Top Vacation Rentals in Chestertown, MD for Your Getaway

Brampton 1860 in Chestertown provides adults-only accommodations with a garden and a shared lounge. There's a sun terrace and guests can make use of free Wifi, free private parking, and an electric vehicle charging station. At the bed and breakfast, some units have a private entrance, dining area, fireplace, and microwave. All rooms are equipped with a private bathroom with a hair dryer, while selected rooms come with a fully equipped kitchen with a fridge. À la carte and American breakfast options with warm dishes, fruit, and juice are available. There is an on-site snack bar. Guests at the bed and breakfast will be able to enjoy activities in and around Chestertown, like walking tours. The bed and breakfast also offers outdoor fireplace and a picnic area for a day outdoors. New Castle Airport is 48 miles away.

- "Warm, great staff and loved having squeaky vist whenever we were outside." - "You'll love it here!" - "Pleasant, peaceful and calming."

While you're here, you can enjoy all the comforts of home and more, including a fenced pool and free WiFi, as well as a flat-screen TV and an outdoor entertainment area. Other amenities include laundry facilities, towels, a picnic area, and firewood.

- "Wonderful weekend on a girls trip, rooms were clean with great ac! We loved Michelle at the pool bar, she makes delicious frozen drinks! All of our food was delicious at the restaurant too. Not crowded and all staff was extremely nice!" - "The Marina and taking a walk along the Chesepeake Bay seeking bay glass " - "Stay was great. Loved the bands and bars. It would be nice if we didn’t have to drive 10 miles for breakfast. Eric is fantastic. Did not know golf was free. ( next time will bring clubs)Is there a website? We got all info from Hotels.com. All staff were extremely friendly and helpful. "

Chestertown Family Hideaway with Kayaks and Deck! is located in Rock Hall. This holiday home provides air-conditioned accommodation with free WiFi. The holiday home comes with 4 bedrooms, a flat-screen TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, a microwave, a washing machine, a fridge and an oven. Towels and bed linen are featured. The nearest airport is New Castle Airport, 93 km from the holiday home.

Parking • Laundry • Child Friendly • Pet Friendly • Internet • Wheelchair Accessible

Hotel with free breakfast, near Washington College
A fitness center, coffee/tea in a common area, and a seasonal outdoor pool are available at this smoke-free hotel. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, a business center, a meeting room, and laundry facilities are onsite.
Comfort Inn & Suites Chestertown offers 81 accommodations with coffee/tea makers and designer toiletries. 42-inch flat-screen televisions come with premium satellite channels. Refrigerators and microwaves are provided. Bathrooms include bathtubs or showers with hydromassage showerheads, complimentary toiletries, and hair dryers.

This Chestertown hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Housekeeping is provided daily.

- "My husband and I stayed here to celebrate his 50th birthday, and to have a weekend away. . Very clean, quiet hallways, very nice staff. Our only complaint and it honestly didn’t effect our stay is that our room smelled musty. The room was very clean and nice otherwise." - "This stay was much better than my last stay. I appreciate the attention to detail in the cleanliness of the room. Great job!" - "1. Everything I need in the same place. Security and comfort for me and my family. "

Free Wifi is available throughout the property and private parking is available on site. The air-conditioned vacation home is composed of 4 separate bedrooms, 3 living rooms, a fully equipped kitchen with a toaster and kitchenware, and 5 bathrooms. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. Guests can enjoy the outdoor swimming pool at Pet-Friendly Home on Chester River with Dock!. New Castle Airport is 48 miles from the property.

Security/Safety • Pet Friendly • Child Friendly • Pool • Internet • Accessibility • Parking • Other • Sports/Activities • Guest Services

Hotel in Chestertown with free parking
This hotel features coffee/tea in a common area, laundry facilities, and a 24-hour front desk. Free WiFi in public areas and free self parking are also provided. Additionally, free newspapers, a lobby fireplace, and a vending machine are onsite.
Change of towels is available on request.
Red Roof Inn & Suites Chestertown offers 53 air-conditioned accommodations with coffee/tea makers and hair dryers. 43-inch flat-screen televisions come with premium cable channels and pay movies.

This Chestertown hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and desk chairs; local and long-distance calls are complimentary (restrictions may apply). Additionally, rooms include irons/ironing boards and complimentary toiletries. Change of towels and change of bedsheets can be requested. Housekeeping is provided daily.

- "Front desk staff was very helpful and friendly. Check in was quick and without a hitch. Doing some renovations but is fine for a stay " - "thanks" - "Staff were very kind. Easy parking and comfortable rooms." - "nice hotel. helpful staff. stores and dining are walkable distances." - "Person checking me in was not very cordial; Other staff folks were pleasant; nice to have daily housekeeping; sign for motel was not visible (actually went to the next door motel); room size was excellent; hall carpet needs replacing"

Located in Chestertown, Comfort Inn & Suites Chestertown offers 2-star accommodations with a seasonal outdoor swimming pool, a fitness center and a shared lounge. The property has luggage storage space and free WiFi throughout the property. At the hotel, the rooms are equipped with a desk. All rooms will provide guests with a fridge. Buffet and American breakfast options are available at Comfort Inn & Suites Chestertown. Speaking English and Spanish, staff are always on hand to help at the 24-hour front desk. New Castle Airport is 46 miles from the property.

- "Latoya was especially helpful" - "Nice clean comfortable" - "I stay here every time I come and visit my mother. Always great service. Great location and easy in" - "Pleasantly surprised by the upgrades made on the rooms" - "Front desk staff were super kind." - "Comfortable and close to mall with pizza" - "One stay here is enough we will look for other alternatives in the area with more welcoming fair policies to all not jus"

Motel in Chestertown with free parking
Along with a 24-hour front desk, this motel has express check-in and express check-out. Free WiFi in public areas and free self parking are also provided.
Driftwood Inn offers 28 accommodations with coffee/tea makers and hair dryers. Premium satellite television is provided. Guests can make use of the in-room refrigerators and microwaves. Bathrooms include bathtubs or showers and complimentary toiletries.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Housekeeping is provided daily.

- "May was very pleasant and helpful. Will certainly return when we are in the area" - "Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip" - "Mrs Mae is very friendly and helpful. Checks on you to make sure everything is ok. I’d recommend it - stayed 3 weeks for work. Loved my little room!! Mrs Mae was a bonus!! " - "I decided to go low-budget for my two-night stay in Chestertown (in town for the Rock Hall Triathlons). This place is convenient and an excellent choice for someone who doesn't plan to spend a lot of time in their room. Rooms are spare w/no frills. Basically four lights in the entire room (overhead, wall, bathroom, shower). Bed was reasonably comfortable. I did notice that the shower temperature control looked a little grungy on the inside; otherwise, the room was clean and fit for purpose. I would stay here again if I were seeking to economize."

This motel is located just a 6-minute walk from Washington College. It offers free Wi-Fi and a 24-hour front desk. Downtown Chestertown, Maryland is 2 miles from the motel. The Driftwood Inn has rooms decorated in rustic wood paneling and soft neutral colors. All rooms include a cable TV with HBO channels, a microwave, and refrigerator. Coffee is provided in the lobby and vending machines with drinks are available. The Inn Driftwood also provides copy and fax services at the front desk. Chester River Yacht and Country Club is 2.5 miles away from the Driftwood. Remington Farms National Wildlife Preserve is a 14-minute drive.

- "No frills, gets the job done" - "I will stay again."

Relax on the scenic Eastern Shore. We are located just off the Chester River. Step away from the hustle and bustle to our cozy cottage appointed with modern amenities. Our property is enjoyed my families and friends.
Our tranquil backyard offers a fire pit and picnic table for entertaining
We have bikes and kayaks for guests to enjoy while they unwind

15 mins from Washington College

The main floor includes a spacious living room, dining room and kitchen.
The second floor offers (2) spacious bedrooms with a loft that includes the bunk beds.
Outside has a spacious deck with a picnic table and grill that overlooks a patio with a fire pit for guests to enjoy in the evenings.
Additional entertainment amenities include (2) kayaks, (2) bikes, horse shoes, and fishing poles.

Guests utilize self check in to access the cottage.
The barn stores the additional amenties (kayaks, fishing poles, bikes and fire wood) for safe keeping and easy access.
Minutes down the road you have access to the Chester River and can spend the day paddling with our kayaks

Self check in for guests. Hosts are available as needed by guests. We are here to help, but not intrude on your trip!

Relaxed riverside community

- "Location is very quiet and tranquil. "

Offering a garden, Carriage House Hideaway In Center of Chestertown offers accommodations in Chestertown. The accommodation is non-smoking. New Castle Airport is 48 miles away.

- "Perfect place for a weekend stay" - "To short, definitely need more than one night to enjoy this gem"

The privacy of a waterfront home welcomes you to pause and enjoy the beauty of the Chester River. Water views from every window connects you to the flowing water and the expansive outdoors. The southern exposure welcomes spectacular sunrises and sunsets. Relaxation and inspiration is abundant in this buffer zone!

Located close to both Chestertown and Rock Hall, it is an ideal gathering space for families and friends with many activities available in the area. By boat, this energetic space is located near Comegy Byte, the Langford Creek and the Corsica River. There is a boat launch within 1/4 mile of the house and a boat slip at the house; water depth is 2.5 feet MLT. Fishing from the 70 ' dock does not require a license.

For outside gathering, there is a large deck by the water with tables for dining, a picnic table under the shade of a holly tree and a water view bistro table and pergola beside the house.

For cooking, you can enjoy our amazing chef's kitchen with single oven, dishwasher, and fully stocked with dishes and utensils, including toaster and coffee/tea bar. You can also cook outside on our gas grill or charcoal grill. If dining inside, you can entertain guests at our kitchen table/dining bar or enjoy the water views at our second dining table.

For relaxation and amenities, we have a fantastic living room and dining area with water views, full size washer and dryer, 2 TVs with Direct TV, high speed internet, books, games and more! We also have an outdoor fire pit and indoor fireplace for entertaining. Firewood is available for your use.

We provide kayaks and paddle boards for you to enjoy the water around the property. We also have bicycles for you to explore the surrounding landscape. A few crab pots are available to try your luck for the famous Maryland blue crab. Bring your own fishing gear to fish directly from our private pier!

Three large bedrooms. Entry level bedroom has a king bed with two single day beds. En suite bathroom with shower and soaking tub. Perfect for families with smaller children.

The second bedroom has a king bed and the third bedroom is a queen. Both have chairs for reading and large closets. One hall bathroom has full bath while the other contains a shower stall. Linens (bed sheets, bath towels and hand towels) are provided with the rental contract. Please contact us if you are interested in opting out of the linen rental during your stay.

Come and fall in love with this retreat; return often!

Keywords: Self-catering, one-story water front cottage

- "Beautifully appointed home - clearly the owners care very much about their property. Tastefully decorated. Everything is in tip top shape - inside and out. Super clean. Nothing is lacking - everything you need is here. Jared - the property manager - is very responsive. Peaceful, quiet neighborhood. Thoroughly enjoyed our stay. Thank you!" - "This is our fourth time staying at Cliff Point and we can’t wait to come back. We enjoyed the beautiful sunrises and sunsets, and how comfortable we feel in this home."

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped with a queen sized bed, linens, washer/dryer, microwave, refrigerator, dinette, toiletries, lux robes... everything you could possibly need to escape the hustle and bustle of life. An additional sleeper sofa, crib, etc. are available at request. Walk to the waterfront or historic district, ride bikes on back country roads. We are more than happy to help arrange paddleboard and kayak adventures! *We require guests to have a verified profile by VRBO OR verification by ID prior to stay*

- "Very quiet location and nice room. Plenty of room. Would have liked a regular coffee maker. And a softer chair to sit on." - "Only stayed for one night but would definitely enjoy more. Amazing family with hospitality that went above and beyond.. Close to town and a nice escape." - "Clean bedroom with bathroom and washer/dryer to stay in while visiting family in the area. The neighborhood is quiet. Our privacy was respected. Owners were available to address our questions. We hope to meet them when we visit again. Linda and Dave"

Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens to call your own. Totally private with views of nature all around, this is the perfect place to relax in front of the fireplace. (Electric, but very cozy and realistic.)
Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and coffee maker.
Comfortable queen bed, kitchenette, and washer dryer.

- "Second stay here this year. It’s becoming our eastern shore home away from home." - "Wonderful place for my wife and I visiting our son at Washington College" - "Just what we needed..." - "A cute studio that had everything, plus walking distance to historic and shopping areas. I would stay there again!" - "Very cozy upstairs studio just off High Street. Well appointed and stocked. I highly recommend it." - "Close to town, easy to get to, clean and tastefully appointed suite, awesome hosts. It truly does not get any better than this!!"

Chester River Dreams, offers spectacular views of the Chester River from the Family room, 2 bedrooms, Kitchen, & Dining room, Deck, not to mention from the 'L' head on the dock. All the other rooms enjoy a view of a large pond where you can watch Osprey, Eagles & Heron enjoy the fishing site. Most evenings you can listen to the Bull frogs sing. There are 3 large bedrooms (3 queen beds + 2 twins.) Each bedroom has smart TVs. Two have views of the river & the other has views of the large pond out front. The family room features a queen sleeper sofa with air mattress & has a view of the river. The family room features hardwood flooring, wet bar w/wine frig, recessed lighting, smart TV, and decorative fireplace. The kitchen & dining area feature an open floor plan with ceramic tile flooring, cherry cabinetry, granite counter tops, & a raised bar between the kitchen & dining area. There are double pocket doors into the family room for privacy. There are sliding glass doors from the dining area that will go out to a large deck that has a cushion patio set & umbrella. There is a laundry area that includes a stacked washer & dryer. All bathrooms have been renovated. There is a full living room with a view of a large pond. Plenty of parking, a small beach, 50' dock w/10X20 'L' head to relax & watch the sunrise or fish/crab. Bar-B-Que grill, (propane) as well as plenty of Adirondack chairs. Kayaks & paddle boat & boards are available (pls note, although there are 4 adults life vests, we do not supply children's life vests. Although, we have young grandchildren & as long as they are not in use, feel free to borrow.) There is also a fire pit for those cool nights or to just hang out and make smoors. High speed internet added in 2021 NEW for 2022! The interior and exterior have been freshly painted. New siding and new living room furniture, new patio cushions, 6 smart tv's & ceiling fans. New for 2025! upstairs bedroom with walk in closet and private bath. HUNTERS WELCOME!! For any of you NASCAR fans, we are situated only 40 minutes from Dover Track. We are also 25 minutes from Rock Hall & 45 minutes from Annapolis. 35 minutes from premium outlets in Queenstown.
** Some dates to consider for fun filled family weeks.
Chestertown Tea Party is every memorial day weekend, Rock fish tournaments usually early June and mid Sept
Sunday on 4th of July weekends is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown and parade in Rock Hall. All times are great with lots to do but, if you have never been to this part of the eastern shore then these are the best times. This whole area is loaded with festivals. Here's a few more.
Bettertown days @ Betterton Beach usually the fist weekend in Aug
The second weekend in Aug is pirate's weekend in Rock Hall another great time to be had. Lots of people dress up for the event. In Chestertown, Sultana down rigging late Oct early Nov, early Dec is Dicken's weekend & early Oct is Rock Hall's Fallfest.
Every Sat. till noon in Chestertown's Fountain park, is the farmer's market. Lots of times on Fridays or Saturday evenings(in season) they have entertainment in Fountain park. On the first Friday of every month is 1st Friday in Chestertown(all year long). Many stores stay open and have snacks (wine & beer too) and some have entertainment all FREE. Lots of people walking around during these events. A great way to get to know the town. 3rd Thurs 6-8 pm is cars on high April thru Oct.
Wilmer park has events as well. There are concerts, taste of the town to name a few. If you are planning a certain week and would like to know the events near town, just ask and I will do my best to list everything I know.
Feel free to surf the web as well. Most of the local towns have event calendars you can find online.
Special winter monthly rentals available (rate does not include utilities for stays exceeding 30 days.) Please be aware, that there are no fences. Neighbor has two dogs that are very friendly and may come over to greet you.
FYI, the school zone has camera 24/7, so watch your speed.

- "We really enjoyed our short visit at your rental home. It was very clean and comfortable and provided everything we needed. We liked it so much we hope to return next year for a longer visit! Thank you for your hospitality. " - "Our stay on the Chester River was great. We had plenty of room for four of us. The accommodations were clean and well appointed. We loved sitting out at the end of the dock and even put a fishing line in the water. The house is very secluded but only a few minutes away from Chestertown and any of the shopping we needed. We would go back again. "

Beautiful1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic Chestertown has to offer as the house is walking distance to the shops, restaurants, Chester River Waterfront, and year round Saturday farmers market. Located on a one way street that is flanked with beautiful historic homes and free on street parking. For those with boats, the home is a short walk to the Chestertown Marina which has a boat ramp and transient slips. Our home is only 2.6 miles from Brittland Manor. Please note there is a ring camera by the front door for security purposes.

- "The property is charming, clean, well-equipped, and located steps to the farmers' market and downtown shops. We would definitely stay again." - "What a wonderful vrbo. Centrally located, charming historic home that was renovated. Really felt like “home”. So much so that the family decided that we’d like to make it an annual tradition" - "This home was nicely decorated with everything well thought out by the owner. Well appointed and clean design aesthetic. Loved the walk in closet; don’t even have that at home. Great to be able to walk to the small downtown area. Very welcoming. Would definitely rent again."

Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath.
Our house is in the historic district of Chestertown, and a two block walk from both Washington College and the Chestertown waterfront. It features two master bedroom suites, one on the ground floor. There are three more bedrooms and a secluded yard. Just outside your garden gate is over an acre of manicured gardens to explore. Gas grill on patio

Over the years, we have stayed in a lot of vacation rentals, and we know what we need as guests.

1. Comfortable beds and furniture
2. Quality linens and towels
3. Limitless hot water
4. Well-equipped kitchen (hate buying
corkscrews!)
5. Peace and privacy, but security in knowing
someone is always available.
6. CLEAN, CLEAN, CLEAN.

Our goal is to give you the experience we would want to have. To maintain quality control we do our own cleaning, and we are available 24/7 if you should need anything, but will be invisible otherwise.
The entire house and fenced yard is yours, as well as the large gardens, which are right outside the back gate. We might be doing some gardening in the large garden, but will keep our distance.

- "Home is meticulously maintained, located on a quiet cut de sac. Walking distance to the restaurants and shops on Main St. Wonderful amenities -- coffee bar, bottled water, etc." - "We were a group of family and friends in Chestertown for a week. Bob and Beth have a beautiful, comfortable house, and there was plenty of room for the seven of us. The house was very clean. The kitchen is equipped with everything you need to have a nice dinner at home. We liked the wine refrigerator, too. We will definitely stay at this property again."

Escape to tranquility at Mill Creek House, a contemporary waterfront sanctuary just 15 mins from Chestertown. Enjoy sunset views from the private dock, watch wildlife, and explore the creek with kayaks. Modern amenities like central AC, WiFi, and a gas grill ensure a comfortable stay.

Nestled in nature's embrace, our cozy house offers a serene retreat with breathtaking views and abundant wildlife. As you step onto the property, you'll be greeted by the tranquil sight of the water gently lapping against the dock.

With two bedrooms and 1.5 bathrooms, our home provides a perfect balance of comfort and intimacy. Every room boasts stunning water vistas, ensuring that you're never far from the beauty of nature. Whether you're sipping your morning coffee in the kitchen or lounging in the living room, the panoramic windows allow you to immerse yourself in the natural splendor surrounding the property.

Outside, the land across from our dock is conserved, preserving pristine scenery that's second to none. You'll often spot bald eagles soaring overhead, a testament to the unspoiled wilderness that surrounds us.

For those seeking adventure on the water, we provide four kayaks for guest use. Explore the tranquil creek, meandering through lush marshlands teeming with life. While the water off the dock may be shallow depending on the tide, kayaking towards the bay offers the perfect opportunity for swimming in deeper waters.

Fishing enthusiasts will delight in the abundance of marine life right at their fingertips. Cast your line off the dock and reel in a variety of species, from rockfish to catfish and white perch. Keep an eye out for ospreys and eagles, ever vigilant as they dive for their next meal, a testament to the rich ecosystem thriving in the area.

Recently dredged, our creek now boasts a channel with a depth of 5 feet, including the spur off the dock, ensuring easy access for boating enthusiasts. Whether you're seeking relaxation or adventure, our waterfront retreat promises an unforgettable experience immersed in the wonders of nature.

- "The home is perfectly located to experience nature on the waterfront with wonderful views. The home is fully equipped with everything and very comfortable. Our couple of friends from France truly enjoyed the espresso machine. We all enjoyed kayaking and fishing. We absolutely recommend anyone who loves nature to stay here." - "It was super peaceful and relaxing. We fished and read and spent the week decompressing and absolutely loved the area!"

Welcome to Eagle Point Farm located on Maryland's beautiful Eastern Shore, a 90 minute drive from Washington DC, Philadelphia or Baltimore. Experience the beauty of the Chester River from this secluded farm located minutes from historic Chestertown, Washington College and the new Kent County YMCA.

Our 350-acre working farm sits on the Chester River and features a private forty-foot pool, a sport court (equipped for tennis, basketball, and pickleball), waterfront access and high-speed internet. There is easy access to fishing in the pond or on the river and kayaking, canoeing or paddle boarding from the private dock.

Resident wildlife includes Bald Eagles, Osprey, Deer, Fox, Migrating Water Fowl of all types and Wild Turkeys. Bring your bike and enjoy Kent County's beautiful, flat country roads. Watch the sunset from the deck or screen porch overlooking the pool, pond, river and corn fields. On cooler days, there are two wood burning fireplaces and a fire pit to gather around.

Historic Chestertown offers restaurants, shops, and a wonderful farmer's market on Saturday mornings. Groceries can be delivered from the local Acme grocery store via Instacart. Local restaurants offer both outdoor dining and takeout options.

Our tastefully decorated home offers four bedrooms with ensuite bathrooms. Three bedrooms have queen beds and one bedroom has two twin beds. We have three desks in the house to facilitate work from home -- one in the main bedroom, one in a queen guest bedroom and one in the kitchen. The main bedroom also has a wood burning fireplace. We provide linens and towels. The upstairs great room, leading to a deck and screened porch, offers spectacular river and farm views and a cozy first floor den provides a second gathering space. The dining room seats eight comfortably and the spacious well outfitted kitchen makes it easy to cook for a crowd. The kitchen is fully equipped including a desk and printer, which when coupled with high-speed internet provides an ideal work from home / remote work environment. We welcome families and pets. We ask only that you treat our house as you would your own.

Property Information & Notes:
o Swimming Pool: Please note our swimming pool is open from May 1-October 1.
o Acreage: 350 +/- acres of complete privacy though the farmer may be working in the fields .
o Fireplaces: 2 Wood Burning Fireplace Ample Firewood on site
o Firepit
o WiFi: High speed internet (up to 1 Gigabit down and up) provided via Talkie.
o Pet Policy: This property is dog-friendly for up to two dogs at an additional charge.
o Grill: This property has a propane grill. Propane is provided.
o Fully equipped Gourmet Kitchen
o Screened Porch
o Outdoor dining
o Walking / Running Trails
o Bass Pond

Keywords: Escape, Privacy, Farm, Eastern Shore, Waterfront House, Chester River, Chestertown, Maryland, Country, Wildlife, Secluded, Pool, Dock, Sport Court, Pickleball, Washington College, Fishing, Maryland Crabs, Rock Hall, Chesapeake Bay, WIFI, High Speed Internet Access, Tastefully Decorated, Social Distance, Remote Work, Work From Home, Desk. Monitors, House, private pool, pickleball

- "I am so grateful to have had the opportunity to experience this place! Beth couldn’t have been more helpful and accommodating! The property is a gem…wide open with a perfect view of the river, yet private! It’s a nature lovers dream. I was impressed by the native landscape and conservation efforts. I think there is a lot of history here and I feel so fortunate we were able to experience this special place! And the beds were SO comfortable!!!!"

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer. We look forward to hosting you!

Our guesthouse is a two-floor 525 sqft unit with a queen bedroom and en suite bathroom upstairs, and a living room with dining/working area and kitchenette downstairs. You'll love the private patio space, which offers separate seating and dining areas with beautiful views of our garden and access to the fully-fenced backyard and grill.

We are proud to give back to our town through the renting of our guesthouse. Five percent of our gross revenue is donated to one or more local non-profits annually. Additionally, the guesthouse features artwork from local artists and galleries, and you'll find home goods and products from nearby shops.

Our place is designed to provide you with everything you need for a comfortable stay, including fast wifi, a private entrance with self check-in via keyless entry, and free street or off-street parking.

You'll find all the essentials like towels, bed sheets, soap, and toilet paper, as well as a hairdryer, cleaning products, shampoo, conditioner, and body soap. There are extra pillows and blankets, and hangers to store your clothes.

The guesthouse has two brand new air conditioning and heating units that you control, so you will be comfortable year-round.

Safety is a top priority, so we have a smoke and carbon monoxide alarm, a fire extinguisher, and a first aid kit on hand. Additionally, for awareness, there is a Ring Video Doorbell installed on the front door of the primary house. It is used to monitor our front door but not the door of the guest unit.

In the kitchenette, you'll find a microwave, dishes, silverware, cups, a mini-fridge with freezer, a hot water kettle, a coffee maker (both a Keurig and a Nespresso), wine glasses, and a toaster.

During your stay you will have exclusive access to the following rooms and spaces:

- Bedroom
- Full bathroom
- Kitchenette
- Living room
- Dining area
- Patio

Additionally, you'll be sharing the backyard with us, but we'll do our best to give you privacy during your stay.

If you have any questions or concerns about the areas you can access, or if you need any additional information about your stay, please don't hesitate to ask.

We're committed to providing our guests with an exceptional experience, and we're always available to answer any questions or provide recommendations to help make your stay unforgettable.

Here's what some of our recent guests have said about their stay:

"Perfect apartment-type accommodation located in a lovely walkable town. These hosts literally thought of a guest's every need... Besides being a comfortable, beautiful space top to bottom with an abundance of windows, the things that really stood out for us are: Self-check in keyless entry, gallery artwork throughout; large stone-top table with chairs for eating, gathering, working, etc; coffee machine with Keurig AND Nespresso pods (WOW!)" - Cindy

"Their place was exactly what I was looking for! It was clean, cute, centrally located, but yet private and offered everything I needed for my stay! I loved the special touches from the local businesses, the espressos, coffee, and tea options. Their place was spotless and the bed was extremely comfortable! They were also very responsive with any questions I had. If I ever come back to the area I will definitely stay at their place." - Megan

"Great place and location. Private and quiet, but walkable to restaurants of Chestertown. Comfortable and super clean! Very cute, indoors and out." - Joan

"Stephen and Marianna were delightful hosts for a perfect getaway weekend in Chestertown! Their detailed suggestions of local restaurants and events made our stay more enjoyable, as were their thoughtful messages to us during our stay to ensure that everything was going well. The apartment is such a gem tucked away in a courtyard at the back of their house in the historical section of town!" - Carla

We're confident that you'll love your stay at our guesthouse, and we can't wait to welcome you.

Book now to secure your spot!

- "Beautiful space… Artfully decorated… Super comfy bed… super convenient location… Lots of nice little extras, like coffee maker, mini fridge, plates, cups, utensils… Beautiful outdoor courtyard, with a nice little space to have a cup of coffee or a glass of wine! Hosts are a great couple- very attentive and responsive…. Hope to be back and stay here again…. highly recommend!" - "We had a very enjoyable weekend at this property. The owners were super friendly and helpful! We would definitely stay here again when visiting the area."

Private, one-of-a-kind waterfront home on the Chester River minutes from historic Chestertown. Drive through a gated entry past your private pool and extensive landscaping to a spectacular vista sweeping the riverfront. Bring your own boat or simply enjoy the recently updated custom Ipe deck featuring pier and floating dock for easy access to the water.
Private beach with walk-in sandy river access is perfect for enjoying provided kayaks (1 adult and 2 child), stand-up paddleboards (2), life jackets included.

Enjoy your morning coffee from the expansive screened porch featuring 180-degree views of the beautiful Chester River. Amenities abound with a hot tub on the additional poolside deck, outdoor shower, provided pool floats, pool basketball and two adult bicycles (bring your own helmets).

The completely renovated and beautifully furnished home features a fully-equipped chef’s kitchen, bar seating and table for 8, sectional sofa and additional seating, bar height table, large screen TV, powder room and first floor master bedroom with magnificent en suite master bath and desk area.

Upstairs, there are three additional bedrooms (1 K, 1 Q) each with a private and updated full bath and access to a waterfront balcony that spans the home. The bunkroom features two sets of twin bunkbeds with trundles and includes gaming system, TV and comfortable kid-sized seating.

Take a short bike ride or walk into historic Chestertown to explore this quaint, historic town. Enjoy the farmer’s market every Saturday, speakeasy, cat café, whiskey distillery, River Packet boat cruise daily, wine and tapas bar, shops and multiple outstanding dining options. Check the town calendar and learn more at www.townofchestertown.com to schedule your visit to take advantage of the many special events held throughout the year. End your day gathered around the firepit to watch the blue herons and ospreys as the sun sets on another day in paradise.

Ask about discounted rates for extended stays.

Property information & notes:
- Swimming pool & hot tub open May 1-Oct. 1. Slide is not available for rental use.
- Ample parking for 3-4 vehicles
- First floor gas fireplace
- Gas Grill with provided propane
- Outdoor firepit
- Upstairs and downstairs full-size washer and dryer
- Freshly-laundered sheets & bath and beach towels are provided for your use
- Starter pack of shampoo, soap and toothpaste provided
- WiFi throughout property
- 4 TV’s with Apple TV and Firestick
- NO SMOKING INSIDE OR OUTSIDE ON THE PROPERTY – will result in immediate eviction
- NO PETS
- Please exercise caution when opening and closing the wall of sliding pocket doors. See instructions in welcome packet.
- Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property.
- Please respect the neighbors and neighborhood.

- "This place is a stunner. Beautiful views in all directions, very private setting, incredibly well equipped. The house is very comfortable. We spent most of our time on the screened in porch or in the large wonderful pool. But paddle boarding and kayaking were on the agenda. And get this...a rental home where EVERYTHING works as it should--the pool, the hot tub, the gas grill, the fire pit, and the appliances. Communication with the owner was excellent. In other words, perfect."

Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of all Chestertown has to offer. This apartment span the entire front of a recently restored building, built in 1877. Open living room/dining area/kitchen Historic character with all modem conveniences, including dishwasher, washer/dryer, TV with AppleTv and high speed wifi internet access. Off street parking for one car on first come first served basis with ample street parking.

- "The unit was really nice and location was perfect." - "The place was clean, well organized and decorated and a fantastic location. Would definitely go back again.!" - "we loved the location and being able to walk to the shops and restaurants in Chestertown." - "Best location to be in walking distance that all Chestertown has to offer. Property was clean and had all we needed and more." - "We stayed in this great apartment and found it to be in excellent condition and in a great location. Walking distance to all the shops, restaurants and bars Chestertown has to offer. The host was great to work with and we will be staying here again on our next trip to Chestertown!"

THORNTON Estate, established in 1664, is a quintessential Eastern Shore estate. The magnificent manor house anchors the 325 acre preserved farm outside of Chestertown Maryland.
Lord Baltimore granted the original patent for Thornton from colonial lands he received from King Charles I of England in the early 17th century. Conveyed to Philip Hopkins in 1693 the estate is still owned by his direct descendants. The current manor house — built in 1815 — was fully renovated in 2008.

- "we felt so safe and relaxed. we were out of the busy of life - Matt was amazing whenever we called he was there in 14 minutes, We will return." - "The property is so beautiful with lots of room to spread out both inside and out. The kitchen is well equipped. It was clean. The pool was lovely. And Matt, the property manager, was extremely nice and helpful. It’s perfect for groups and we will definitely be back!!" - "Three of us rented this property for a long weekend and it was absolutely magnificent! The property managers were outstanding, we had complete privacy, and the house did not disappoint! We look forward to returning!"

A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet kitchen, two porches, antiques, rugs, and several writing spaces. Dual zone HVAC, washer & dryer, high-speed internet. Off-street, garage parking with a super-charger and outlet for other electric vehicles.

The main bedroom has a walk-out porch and huge closets. The second bedroom has a high ceiling and comfortable antiques. Two bathrooms are also on the second floor. The third floor has a cool kids/teenager space with three twin beds. The front room has a sofa bed.

The kitchen has a gourmet gas range, warming oven, microwave and collectible china. The spacious living area has a wood stove, and access to a shady porch and small garden with pond.

Holiday home for an easy going, busy family of five. Always glad to make new friends from around the world and give suggestions and advice on your trip. Also, always glad to leave you alone to do your own thing.

- "We were in town for a family event and found this lovely Victorian to be a perfect home base. Clean. Spacious. Nicely decorated. Great chef’s kitchen. Comfortable space to hang out. Walking distance to town. Thank you!" - "Beautiful property. Property owner was very kind & professional." - "A great stay.No problems." - "The reservation process was easy and we were delighted with the property. The Victorian has loads of charm and an expansive and well stocked gourmet kitchen. The house has covered porches and a pretty fountain in a courtyard with garden. Altogether a worthwhile rental. We’ll be back."

Welcome to Goose Landing, our serene waterfront haven nestled on over three acres along the beautiful Fairlee Creek. We're thrilled to share our secluded 4-bedroom, 2.5-bathroom home with you, offering 350 feet of private waterfront and breathtaking panoramic views.

Unwind and explore at your own pace. Enjoy the peace and quiet, gather around the fire pit for cozy evenings, and take advantage of our complimentary kayaks and canoe to explore the tranquil waters. Our private dock is perfect for year-round fun, whether you're into water skiing, kayaking, or fishing. Bringing your own boat? Feel free to dock it with us at no extra charge! For some friendly competition, shoot some hoops on our basketball court or enjoy a game of badminton.

A Birdwatcher's Paradise!
Birding enthusiasts, you're in for a treat! Fairlee Creek is an incredible spot for birdwatching, teeming with a rich variety of bird species typical of coastal Maryland. Keep an eye out for waterfowl, majestic raptors, and delightful songbirds. We've personally spotted a diverse array of feathered friends, including:
• Red-bellied Woodpeckers
• Cardinals
• Blue Jays
• Tundra Swans
• Bald Eagles
• Osprey
• Baltimore Orioles
• Canada Geese
• Snowy Egrets
• Wood Ducks
• Cormorants
• Great Blue Herons

More Ways to Enjoy Goose Landing!
Goose Landing is the perfect place to practice yoga amidst the calming sounds of nature and stunning waterfront views. Find your flow and rejuvenate your mind, body, and spirit in this peaceful setting.
Looking for an even more immersive outdoor experience? We can also accommodate camping on the property, so you can truly connect with nature under the stars.

We are happy to consider special rates for small groups and family reunions, making Goose Landing the perfect destination for your next gathering. We're also happy to help make your stay extra special. Just let us know if you have any special requests.

Come experience tranquility and adventure at Goose Landing!

The space

Sleep
Our spacious home is designed with families in mind, offering four comfortable bedrooms. The primary bedroom, located on the first floor, features a king bed and an attached private bathroom. The remaining bedrooms are upstairs, accessible via a charming spiral staircase. Bedrooms 2 and 3 each have queen beds, while the fourth bedroom is perfect for kids, with a queen bed and two twin bunk beds. An additional bathroom is also located upstairs.

Entertain
Goose Landing is perfect for family fun and entertaining. The large great room with TV and billiard table is ideal for cozy gatherings. Multiple outdoor deck areas, a screened-in porch, and a patio provide plenty of space to enjoy the fresh air. The expansive yard includes an asphalt play area with a basketball hoop, as well as badminton and pickleball nets (not regulation size) for hours of fun. The well-equipped kitchen, complete with a large breakfast bar, invites everyone to join in the cooking. We even have a piano for our musical guests!

Logistics
Our driveway accommodates 3-4 cars. For your convenience, the home is equipped with a keypad door lock, and your code will be sent to you the day before check-in.

For those looking to bring boats during their stay, Fairlee Creek Public Landing is 1/4 mile away and you are welcome to dock your boat on our private dock during your stay. The center of the creek can be counted on to have 3 feet at mean low tide. Typically, the average is closer to 4-5 feet in the center and next to our dock is 2-3 feet of depth. Anyone bringing a boat will need to provide proof of insurance.

Bring your family to Goose Landing for a memorable and fun-filled getaway!

Guest access
Guests have access to the entire property, including the dock, kayaks, canoe, and sports courts. Please be mindful of our neighbors, as sound carries easily along the waterfront. We appreciate you respecting quiet hours between 10pm -10am. Guests will be required to sign a liability waiver for the use of these amenities. This is not a party house.

Other things to note
While we admire and appreciate fury friends, we do not allow them in our home. If this is an issue, we are happy to provide information on pet boarding as an alternative during your stay.

This is our personal vacation home, so you may notice some of our personal belongings around. We kindly ask that you leave them as they are while you are visiting.

Please note that if you cancel a booked reservation, and it is within the timeframe for a full refund, you will receive the refund minus the credit card processing fee of 2.9%.

- "Lydia and John's property is just lovely. A great layout and space to feel cozy but also with room to oneself when needed. We used it all: the dock and family room, the patio and dining area... It was just so special that I hated to leave. We're already planning our next retreat, if they'll have us! Totally worth it:)" - "Our vacation was absolutely perfect. The location was remote enough to disappear, enjoy daily paddles in the kayaks, and do some fishing off of the dock; we even caught a catfish big enough to snap the line, which thrilled my son. The amount of wildlife and birds we saw was unreal. We saw 10+ bald eagles (we even saw one dive into the water to catch a fish), 10+ herons, and plenty more. The house itself was amazing. It's perfectly tucked in the woods, which allowed us to barely even need the AC. We spent a ton of time eating meals and playing games on the screened in side porch. On Lydia's recommendation, we went to Eastern Neck, and our family loved the butterfly trail there. We even made the trip out to Assateague Island, which was a longer day trip but well worth it! The town of Chestertown has a ton of charm as well. It was everything we were hoping for and more. We don't return to many vacations spots - we usually prefer going to see new places - but we will definitely be back to this one!"

Welcome to Riverfront Retreat, a beautiful and spacious home where your family will be able to relax and enjoy the best of the Eastern Shore. With two main floor bedrooms, including a master suite accompanied with sitting room with full river views. The second main floor bedroom, our Library Bedroom, is spacious and features hardwood floors and built in bookcases. The four large bedrooms on the second floor provide plenty of room to spread out and enjoy. Two of the upstairs bedrooms have their own bathroom, and a jack-n-jill bathroom serves the other two bedrooms.

The main floor living areas are equally built to please - the 33X24 combination LR/DR with hardwood floors and a cathedral ceiling is a great spot for family meals around the 14 person dinner table, and for games, all while looking out at the river. Get closer to the river on the deck, which receives mid-day sun, as well as shade from the large Magnolia adjacent to our home.

The main floor kitchen is fully equipped with a large center island, breakfast dining area, and another set of breathtaking views of the river. The ground floor features a great room with pool table, 75 inch television, and views of the river.

Prefer to eat outside? The ground floor also includes a substantial screened-in-porch, complete with two ceiling fans, as well as a table with seating for eight that is ready for you.

Beyond the many attributes of the house itself, the property features a 110 foot private pier, which is great for launching the kayaks that are provided for your enjoyment (4 single, one double), the paddleboard, swimming, and there is a mooring at your disposal if you want to bring your power boat.

All of this, and you are about a four block walk to historic Chestertown.

We purchased the home in November 2020 from the original (1989) owners, and we love this place! In early 2021 the main entry, LR/DR, MBR, Library bedroom, and all upstairs bedrooms were freshly painted and updated. The furniture in the LR/DR and breakfast room is fresh too. Likewise, the furniture on the ground floor, in the great room and the screened-in porch is all fresh. The pool table in the ground floor great room is a classic, which we purchased from a Chestertown resident, and we had it re-felted in the spring of 2021.

The main floor, primary kitchen is spacious and has served us as a wonderful gathering place, and it has original appliances including an electric stove. The ground floor, secondary kitchen is smaller and functional.

Our home is in a wonderful residential neighborhood. Most of our neighbors live in Chestertown year-round. It is important to us to be good neighbors, and so we aim to rent our home to people who want to use it for relaxing, fun vacation getaways - people who will use our home the same way we do. We want and need to be sure that our renters respect our neighbors and avoid any disruptive behavior - things like loud music, other excessive noise, or bright lights, particularly after hours. Likewise, parking is limited to six vehicles, which need to be kept on one of the two driveways. If you are looking for a beautiful home in a great area, with plenty of fun things to do, please come to our River Retreat!

- "The house was perfect for a multi-generational family reunion. The house was clean, and the kitchen, bedrooms and bathrooms had everything we needed for our stay. The property manager was very helpful and easy to contact with questions. We enjoyed the water and beach and walking to Chestertown." - "The whole family enjoyed this beautiful house. We also enjoyed the convenience of the dock right outside the backyard. The short walk into town was also nice"

Modern cottage on tranquil large grounds on 20 acres with a pond on one end and a half mile wide creek 800 feet away on the other with a 100 foot dock. Inside a larger historic 18th century farm with original house and buildings. Expansive views. See beautiful sunsets, birds, deer and more. The salt water pool is shared only with the main house on certain dates in the summer. Guests will have the pool area 6 hours a day to themselves (to Oct 1). Recently renovated and furnished. Outside back yard seating and eating area with BBQ. High speed fiber internet, smart TVs. 2 fat tire bikes available. Central AC and heat. Seating on dock and water with fire pit. Easy access, parking, ground floor Master.

- "Delightful spot. Well supplied lodging. Many acres of beautiful land and water. Rich variety of wildlife." - "lovely grounds " - "Our stay at the Beatrix Cottage in Chestertown was just perfect. It is in a serene and secluded area with lots of wildlife and natural beauty. The dock area allowed for beautiful sunset views. The saltwater pool was perfect and plenty of time was offered to use it while sharing with the owners. Communication with the owner was excellent and all issues were addressed promptly. This was the perfect quiet getaway for my family. I highly recommend this idyllic spot."

Down a half mile lane, surrounded by woods and farm land. This property is located between Chestertown and Rock Hall, Maryland. Just a half mile away from the Chesapeake Bay, this cottage is a wonderful vacation get away. The great room has a queen size pullout couch. Great birding, kayaking, biking and a private beach at Tolchester Marina.
Tolchester has live music on summer weekends and a Tiki Bar!

- "Everything one could need was easily at hand in this comfortable, clean and pleasant cottage. Beautiful setting and appealing home-like atmosphere. Would definitely stay again!" - "We had a great time staying at Tracy's place! Check in was easy- we picked up a key from Tracy at the Inn. Tracy had a whole list of recommendations for local restaurants (even one that delivered). She also suggested local attractions to check out, which was very helpful as we had never been to the area. The cottage gets a 10/10 for cleanliness and coziness. The kitchen has everything you need to make meals, the bed and couch are comfortable and the fire is relaxing. Even though we were in the cottage we were still offered breakfast, which was nice. The breakfasts were great and we even got to enjoy some homemade bacon jam. We had an awesome and relaxing time and we'll definitely go back soon."

Welcome to our charming Chestertown Home! This beautiful house offers a comfortable and inviting space for your stay. With two full bedrooms and bathrooms on the second floor and a cozy third-floor retreat with two twin beds, there is plenty of room for everyone.

Conveniently located behind the house, you will find three reserved off-street parking spaces. Upon entering the back gate, you'll enter a tranquil courtyard perfect for a barbecue. The screened-in porch leads directly to the well-equipped kitchen, with all the essentials and appliances you need to prepare home-cooked meals.

Adjacent to the kitchen, you'll discover two separate relaxation areas, each providing a cozy atmosphere to unwind. A full bathroom is also conveniently located nearby. On the backside of the house is a dining room/living room with a television, offering access to popular streaming services like Netflix, Hulu, and Disney+.

On the other side of the kitchen, you'll find another inviting living room featuring a gas fireplace, creating a warm and cozy ambiance. You'll find the entryway and front door at the end of this living room. Step outside onto the lovely porch, where you can enjoy your morning coffee or evening drinks while taking in the surroundings.

Head up the wooden stairway to the second floor, where you'll discover two spacious bedrooms, each with its full bathroom for added convenience. The third floor offers a peaceful retreat with two twin beds for those traveling with children or additional guests.

We invite you to make yourself at home. Experience comfort, convenience, and a relaxing atmosphere during your stay.

- "The location and home were perfect for a weeklong vacation with my wife and two daughters (ages 13 and 10). Easy walking to restaurants, especially ice cream! Lots of days visiting the community pool 10 minutes away, followed by using the grill in the backyard, walking down Main Street shops, and evening board games. Even drove into Washington DC for a day trip of sightseeing. Home was perfect for our family and we would visit again. Communication with the owner was great, and we really enjoyed the visit."

Quaint and charming, our home away from home in historic Chestertown features 2 bedrooms and 2.5 bathrooms and can accommodate up to 4 adults. Just a few blocks from the downtown shops and restaurants. Also walkable to Washington College.
The space
Some additional features of our home:

- Extremely fast and reliable fiber optic internet
- Dual zone central a/c and heat
- Both bedrooms have queen beds with Sealy Posturepedic mattresses, 600 thread count sheets, and down comforters
- Each bedroom has a large closet and private en suite bathroom
- Additional half bath downstairs
- One TV - in the living room - and it's equipped with YouTube TV
- Beautiful kitchen with gas range and seating for 6
- Brick patio with string lights and 7 foot picnic table for your next crab feast
- Back porch has 2 Adirondack chairs perfect for enjoying your morning coffee or evening cocktail

- "Would stay again- perfectly located, beautiful, well renovated!" - "Was in town for a lacrosse game. This property was ideally situated off High Street and close to everything. Comfortable, great back yard and all the features. Definitely will be back." - "Super cute house right in historic downtown Chestertown MD. Walkable to just about anywhere you would want to go -- all the charming shops, restaurants, the beautiful Chester River Waterfront, and of course Washington College campus, and Lacrosse Field. The house is perfectly appointed and warm and welcoming. Super comfortable beds, good pillows, sheets and towels. Overall a very nice surprise! Easy communication with the host too!"

• Embrace historic charm in our exquisitely renovated third-floor walk-up, located in a beautiful historic building in the Chestertown Historic District.

• Perfectly positioned to overlook Fountain Park and within walking distance of Washington College and all of downtown Chestertown.

• Enjoy unique furnishings that blend early 1900s decor with modern comforts.

• Indulge in luxury amenities with priority booking access at Park Row Floats, a renowned exclusive Float Spa located just below the space.

Pippin’s Retreat offers:

• Two bedrooms, each featuring a queen bed.

• Two full bathrooms, with the primary bedroom offering an ensuite.

• A large, fully-equipped modern kitchen with a view of Fountain Park.

• A comfortable living room with characteristic furnishings, opening onto a sizeable back deck - perfect for relaxing or entertaining.

• We use Melaleuca's nontoxic, plant-based cleaning products to ensure a healthy, chemical-free environment for your stay.

Guest access
• You will have the entire third floor to yourself, including the large back deck that provides an elevated view across the historic rooftops of Chestertown.

• Access through the rear exterior staircase or enjoy walking up the original historic stairway inside the main front lobby, with its charmingly narrow design reflective of the early era.

Other things to note
• We cherish the building's historic elements and ask guests to be mindful of the unique charm of the narrow staircase.

• Visit the Park Row Floats website to make a Spa appointment.

• We use Melaleuca's nontoxic, plant-based cleaning products to ensure a healthy, chemical-free environment for your stay. These eco-friendly cleaners leave your space fresh and welcoming, perfect for guests with sensitivities or anyone looking to avoid harsh chemicals. Relax knowing your comfort and the planet are prioritized - ideal for Washington College parents cheering on their students!

- "We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."

Welcome to Lovely Cove Farm. Close to Chestertown and Rock Hall for shopping and dining, but a world away. Secluded and serene spot for birders and boaters and stargazers. Bald eagles, osprey, herons, songbirds and migratory waterfowl can be seen as they go about their daily routines. And a public boat ramp is nearby. Come by boat or land. Enjoy a dip in your private pool before cooking in the gourmet kitchen. Or grilling outside on the gas grill. The skies at night are dark enough to enjoy constellations, meteors and the Milky Way so vividly and memorably.

Enter the house and be amazed with the views throughout with large windows overlooking East Langford Creek. There is a lovely living room which opens to the outdoor deck and screened-in porch. The first floor includes the living room, kitchen, dining area, a sitting room, powder room, and an office with a daybed.

The second floors have 2 staircases. The one has the master suite with ensuite bathroom. There is a Queen bed and a daybed. The main staircase takes you up to 3 more bedrooms and a hall full bathroom. Bedroom 2 has 2 twin beds. Bedroom 3 has a king bed, and bedroom 4 has a full bed.

The pier can be used for fishing or crabbing. Or, to tie up your boat. There is a floating pier which can be used to launch the provided kayaks or canoe.

The pool is for your personal use. Sorry, no daytime guests.

Child Friendly • Fireplace/Heating • Bedding/Linens • Pool • Security/Safety • Tv • Wellness Facilities • Laundry • Balcony/Terrace • Kitchen • Entertainment • Private Pool

Experience the charm of Chestertown, Maryland by indulging in a stay at our upscale vacation residence. Located just a stone's throw away from the vibrant town center, you'll find a plethora of shops, cafes, and restaurants waiting to be explored.

Come visit us in Downtown Chestertown at our 2-story brand new luxury apartment! This apartment is on the 2nd and 3rd floors of the property. There is no elevator.

This apartment can fit 7 people comfortably. There are two bedrooms, one on the second floor and one on the third floor. On the third floor are three built-in single beds. There are 2 full baths and one half bath. This apartment is perfect for a family stay with a large kitchen and living space.

**This listing is for the upstairs apartment only and does not include access to the back patio space or downstairs apartment.**

Guests have access to the property's front porch, which is a shared space. Guests will not have access to the ground floor back patio/outdoor space. The back patio area is for the downstairs unit only. Free on street parking.

- "Our stay was absolutely perfect! Your home is stunning and we appreciated your kindness and generosity with the snacks and drinks already there for us to enjoy. We will definitely be back!! "

This modern luxury unit boasts a first-floor apartment with two bedrooms, full access to a private back patio/outdoor space, beautiful kitchen with dining area and shared front porch.

**This listing is for the downstairs apartment ONLY with access to the back patio area. There is no access to the upstairs apartment.**

Guests will access their luxury apartment via a smartcode with our smartlock system. Codes will be given prior to check in for front door, unit door and back patio door.

Front porch is a shared space. Back Patio outdoor space is private for this apartment only. Smoking/Vaping allowed in this space. Free on street parking.

Guest Services • Bedding/Linens • Air Conditioner • Child Friendly • Other • Entertainment • Tv • Kitchen • Parking • Security/Safety • Fireplace/Heating • Pet Friendly