Best Vacation Rentals in Harpswell

7.2 miles from Bowdoin College in North Harpswell, Casco Breeze features accommodations with access to a fitness room. Guests can benefit from a patio and an outdoor fireplace. Outdoor seating is also available at the vacation home. The vacation home consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a walk-in shower and free toiletries. Towels and bed linen are available in the vacation home. There's also a seating area and a fireplace. There is an on-site restaurant. Portland International Jetport Airport is 35 miles from the property.

- "Great location and amazing views!" - "Magical place" - "GREAT Stcy!!" - "This is a gorgeous home, but it needs some TLC."

Immerse yourself in the beauty of Maine's coastline with a vacation rental at Woodbine Cottage. Enjoy stunning views, fishing off the association dock, and explore walking paths along the shore and through classic Maine woods. Perfect for a relaxing getaway in a serene coastal setting.

- "Everything about our stay was flawless. The instructions and communication prior to arrival were complete and clear. Anne is a fantastic hostess whose attention to detail and thoughtful gestures made our experience truly unforgettable. She met us at the cottage and made sure we had everything we needed for our stay. She also mailed something back to us my daughter forgot and left behind. The property was clean and cozy, beds were comfortable, and the kitchen was well stocked. It was evident that Anne puts a great deal of effort into maintaining a clean, comfortable and welcoming environment for her guests. The thoughtful touches and amenities provided by her truly made us feel welcome. We watched beautiful sunsets from the porch and enjoyed the refreshing sea breeze. We were also able to observe the eagles on the nest which made this trip even more special for us. We enjoyed this cottage immensely and would definitely return in the future."

Clark Cove offers accommodations in Harpswell Center, 10 miles from Bowdoin College. The vacation home has access to a restaurant. On clear days, guests can head outside to enjoy the vacation home's outdoor fireplace or simply kick back and relax. Featuring a patio and sea views, the spacious vacation home includes 2 bedrooms, a living room, satellite flat-screen TV, an equipped kitchen, and 3 bathrooms with a bath and a shower. Towels and bed linen are available in the vacation home. There's also a seating area and a fireplace. Portland International Jetport Airport is 39 miles from the property.

Sports/Activities • Laundry • Private Beach • Security/Safety • Restaurant • Child Friendly • Fireplace/Heating • View • Guest Services • Barbecue/Outdoor Cooking • Ocean View • Balcony/Terrace

This second floor unit comprises of two bedrooms and one bathroom. *Important to note: The bathroom can only be accessed through the master bedroom.*

The updated kitchen has new stainless steel appliances and a dishwasher. Kitchen is outfitted with a four person dining table and all the amenities you'll need for your stay including cooking essentials.

The smaller front bedroom has a full-sized bed, closet, dresser and stand up fan but no cooling. This room gets great morning sun and is perfect for early risers.

The master bedroom has a king-sized bed, seating area with leather recliner, built-in closet, wi-fi connect TV for streaming and the en-suite bathroom. This room also has a split system to provide all heating and cooling needs.

The only bathroom is accessed through the master bedroom and is fully updated with recessed lighting and a walk-in shower. All necessary linens are supplied.

The outside deck boasts comfortable chairs and a gas fire pit, great for Maine's cooler summer nights. From the deck you'll be able to view the gardens, driftwood sculptures of local artist and catch ocean glimpses through the trees.

- "The place was so cute and perfect for me and my husband! We found it to be the perfect location! The owners were so friendly and helpful! We want to go back someday and we’ll definitely stay here again! The place was immaculately clean!" - "The property was very clean, in a good quiet location, and the host was especially attentive and went above and beyond in providing us a stock pot and utensils to cook lobsters."

Tide's Edge offers accommodations in Cundys Harbor, 12 miles from Bowdoin College. The vacation home has access to a restaurant. On clear days, guests can head outside to enjoy the vacation home's outdoor fireplace or simply kick back and relax. The air-conditioned vacation home also features a TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 3 bathrooms with a walk-in shower. The property offers sea views. Guests at the vacation home will be able to enjoy activities in and around Cundys Harbor, like cycling. The vacation home has a picnic area where you can spend the day outdoors. Portland International Jetport Airport is 40 miles from the property.

Balcony/Terrace • Fireplace/Heating • Guest Services • Pet Friendly • Sports/Activities • Restaurant • Security/Safety • Barbecue/Outdoor Cooking • Ocean View • Laundry • Private Beach • View

Beachfront bed & breakfast for sun and fun
A private beach, free use of bicycles, and a garden are available at this bed & breakfast. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include a picnic area.
Housekeeping is available on request.
Harpswell Inn offers 11 accommodations. Guests can surf the web using the complimentary wireless Internet access (speed: 50+ Mbps). Change of towels and change of bedsheets can be requested. Housekeeping is provided on request.
A private beach and complimentary bicycles are featured at the bed & breakfast.

- "Nice country inn, beautiful views. best wishes for the new ownwers." - "Had a great stay. The owner was SO welcoming. The setting is beautiful!!!!" - "Just the road leading to the property is cluttered with junk cars etc. otherwise beautiful property and amazing sunsets over the ocean"

Harpswell Retreat offers accommodations in Cundys Harbor, 11 miles from Bowdoin College. Guests can benefit from a patio and an outdoor fireplace. With direct access to a balcony, the air-conditioned vacation home consists of 2 bedrooms. Offering a terrace with sea views, this vacation home also has a satellite TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a walk-in shower and a hair dryer. The property has an outdoor dining area. Guests may enjoy a meal at the on-site restaurant. Guests at the vacation home will be able to enjoy activities in and around Cundys Harbor, like cycling. The vacation home has a picnic area where you can spend the day outdoors. Portland International Jetport Airport is 39 miles away.

- "Excellent enjoyed my stay" - "Great place for a quick getaway from Boston!" - "It was a charming getaway spot that served 3 of us perfectly that I would highly recommend." - "I highly recommend this rental to family and friends" - "Amazing place for a couple but not great if you need a second bedroom"

Feel the gentle breezes, watch (or try to catch from the dock) fish as they are flipping, see seals playing, and view boats hauling their famous catch of crustaceans from the many incredible vantage points offered by this cottage. You can enjoy the back patio with a gas fire pit, the sun porch for BBQ lunches, and even the screened porch for relaxing when the bugs come out. You are welcome to join us next door for a nightcap at their "martini bar" for additional conversation and local insight while enjoying stunning views! Harpswell is made up of Harpswell Neck, which is contiguous with the Town of Brunswick, as well as three large islands connected by bridges: Sebascodegan Island (locally known as Great Island, where the cottage is located), Orr's Island, and Bailey Island, along with over 200 smaller islands. Harpswell is a short 30-minute drive to Portland, 45 minutes to Boothbay, 47 minutes to Augusta, and an hour to Camden. And of course, the world-famous L.L. Bean flagship store is just a quick 20-minute hop to Freeport. This central spot in Harpswell is perfect for exploring the Midcoast. This is truly the way life should be!

Bedding/Linens • Laundry • Kitchen • Barbecue/Outdoor Cooking • Fireplace/Heating • Security/Safety • Air Conditioner • Internet • Balcony/Terrace • Other • Wellness Facilities • Child Friendly

Free Wifi is available throughout the property and Bowdoin College is 7.3 miles away. Featuring a patio with river views, this vacation home also includes a TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a walk-in shower and free toiletries. The property has an outdoor dining area. Guests at Casa Familia can enjoy cycling nearby, or make the most of the garden. The nearest airport is Portland International Jetport Airport, 35 miles from the vacation home.

Balcony/Terrace • Other • Child Friendly • Guest Services • Security/Safety • Sports/Activities • View • Parking • Barbecue/Outdoor Cooking • Internet • Fireplace/Heating • Laundry

Your cozy “bungalow” is part of an incredible 8-acre private estate with a private beach, walking trails, cliff views, a shared deep water dock, and even a freshwater swimming pond. The Bungalow is an 800 sq ft heated modern post & beam structure providing ample living space with a modern kitchen, two bedrooms (one queen, one full), and a 300 sq ft living/dining room area with an adjoining screen porch. There is also a bathroom with a tub/shower that includes a washer and dryer. Off the porch is a private lawn with four Adirondack chairs, a fire pit, and a BBQ.

You are just a short walk through open fields to a private ocean beach perfect for launching your kayak. Continue your walk to a shared private dock great for swimming. Our dock is on the local harbor at Lookout Point and faces westward for fantastic sunsets and expansive island views. This is an active lobstering harbor so you can purchase your lobsters right next door!

The Bungalow is located on an incredible 8-acre private family estate in a lush field surrounded by 1,500 feet of ocean frontage. You get to share this calm and quiet estate with a family-owned cottage and year-round home while having your own secluded corner all to yourself.

So come swim off the dock, launch your kayak, swim off the rocks, read a book, have a lobster, take walks . . . just relax and enjoy!

- "Excellent location for cozy hygge cabin." - "I can't begin to tell you how wonderful this house , location and owners are. It's peaceful, it's clean and tastefully decorated. It's easy to find and yes there are things o do around the area but why leave this beautiful scenery. Susan is probably the friendliest host that I have rented from. I can't wait to come back next year!!!" - "I can't say enough positive things about this experience. The bungalow is situated so that when you're sitting in the living room and looking out window you see the cliffs and the bay. Looking out the kitchen window you see the pond. The bungalow was very clean and had everything we needed. The owners, Susan and Ned, were extremely friendly and respectful of us. We definitely plan to go back during a time that everything has re-opened after the winter season."

Free Wifi is available throughout the property and Bowdoin College is 11 miles away. The vacation home consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a bath and free toiletries. Towels and bed linen are available in the vacation home. The property offers sea views. Guests at Harpswell Beach House can enjoy cycling nearby, or make the most of the garden. Portland International Jetport Airport is 39 miles from the property.

View • Security/Safety • Pet Friendly • Other • Sports/Activities • Laundry • Internet • Child Friendly • Parking • Guest Services

Cozy Sunny Oceanfront Cottage on your own private point with 250ft of coastal frontage and unobstructed ocean views from each of the 8 windows in the living room. Experience peace and tranquility as you gaze at the golden sunset reflecting across the water. Enjoy the wonder of nature as you watch our local bald eagle, loons, Canada geese, ducks, deer, turkey and many local birds. Watch the lobsterman pull his traps, seagulls harvest their clams, and osprey dive for dinner….. or cast your own fishing pole off the rocks and fish for stripers … just steps from your front door. Nature's entertainment is constantly changing just outside your window. It’s no wonder that Maine nurtures so many artists and poets. Our beautiful surroundings are the inspiration for the poet to translate words into emotion and the artist to transform paint into a vision.
The cottage is 5 minutes from Brunswick which hosts an abundance of great restaurants, shops, cinemas, golf courses, museums, bike and walking paths, and the popular Maine Music Theatre. Smithsonian Magazine voted Brunswick as one of America’s best small towns in 2012. Maine’s largest city, historic Portland, is only 45 minutes away…..Although one would wonder why you would ever want to leave. So sit back, relax, and remember days gone by, when life was simpler and vacations were a time for rest, relaxation and renewal.

- "The hosts of this retreat, Diane and Larry, could not have been more welcoming or informative. Diane has a very well organized "tourist booth" right inside the cabin: sightseeing, restuarants, museums and many other area attractions. This cabin is truly special as it sits on it's own little pennisula, away from the big house so it's very private. Really clean and well organized kitchen, but the bathroom is kinda small. But hey, you're in a cabin in the Maine woods not a spa lol! It too is just right...the bedroom has a comfy king bed with a good variety of pillows to lounge around on after your hikes or touring lighthouses. There's a table in front of the big windows which face west for the fantastic sunsets. the table has a drop leaf so you can have your coffee there and plan your day. The yard has access to the water so you can toss a fishing line in if so inclined at high tide. And the entire property itself is so beautifully landscaped with flowers blooming in all the right places!! We had such a relaxing vacation there we are thinking of going back in the fall. Thank you Diane and Larry for such a great week in Maine! Mary & Steve"

Oceanfront Studio with Private Dock in Harpswell! offers accommodations in Dyer Cove, 11 miles from Bowdoin College. With sea views, this accommodation provides a patio. With free Wifi, this apartment offers a TV, and a fully equipped kitchen with a microwave and toaster. Towels and bed linen are featured in the apartment. For added privacy, the accommodation features a private entrance. Portland International Jetport Airport is 39 miles away.

Parking • View • Internet • Ocean View • Security/Safety • Child Friendly • Other • Sports/Activities • Guest Services • Oceanfront

Completely renovated and will be ready for 2025! Pictures coming soon! This beautifully located downstairs apartment is just feet from the water's edge. You can hear the waves at night feet from your window and smell the salt air. Wake up to lobster boats on the water and the sight of eagles flying around the shore that surrounds you. Pets are welcome here at Hopkins View but there is an accompanying “per fee” per night.

- "A most enjoyable stay. Clean, comfortable (even the bed) and what was represented online accurately reflected what we found when arriving." - "Lovely, cozy cottage on the water. Beautiful views all day as the tide comes and goes. Comfortable furniture, quality linens and nicely stocked kitchen equipment. Perfect for one or two people who’d like to enjoy the experience of being right on Maine’s coast. Lots of lobster dinners at nearby restaurants and seafood shacks. We had a wonderful time."

Sitting 10 ft from the water's edge, this 1 bedroom 2nd floor unit has beautiful views of the working waterfront community of Cundy's Harbor. This beautifully located unit is the full second floor of a two unit property. The unit has its own outside stairway to the entry door on the 2nd floor. With its 10 x 25 foot wrap around deck, you can relax in a deck chair or eat dinner and play games at the table provided.

Launch your Kayak from the front yard and explore the rocky shore that surrounds the edge of the yard. There is also public boat ramp just moments away. With the changing of the tides the shoreline may look different each day. Watch for wildlife, seals, eagles and a variety of birds make the Maine coast their home in the summer.

With an open floorplan this unit is cozy and welcoming. Two large couches and a recliner make the area comfy for watching the 65 inch smart screen TV, The fully stocked galley kitchen has full size appliances, dishes and utensils, including a coffee maker, air fryer, 2 slice toaster and blender. The bedroom has a queen bed, the bathroom has a single sink and shower, no tub.

Located in the small community of Cundy's Harbor, take a walk around the village, explore the working waterfront community and see lobsters being brought in at the end of the day. Take a drive and see all that Harpswell has to offer from gift shops, restaurants, sailing excursions, free summer concerts, to candy and ice cream shops. Fun Fact: the town of Harpswell has 216 miles of coastline! That is a lot to explore.

Feel like a break from the coast? Freeport's famous LL Bean and a variety of outlet stores are less than 30 minutes away. Brunswick, only 15 minutes away, is home to Maine State Music Theatre, Bowdoin College with its museums, as well as a thriving downtown area with shops and restaurants. We also have 4 local golf courses.

We welcome 1 Dog under 50 lbs with an additional per day charge of $60.00 per day.

We recommend a car for your stay here in Harpswell, Osprey's Nest is located 15 minutes from major grocery stores and the town of Brunswick. If you will be flying to Maine, we recommend Portland International Jetport (PWM). If assistance is needed for varying flight arrivals of your party, Safe Harbour Property Management offers concierge rides to and from PWM starting at $125.00.

Kayak rental and rate inquiries may be found at:
Seaspray Kayaking 207-404-1100
Rings Marine Service 207-865-6143

- "From the moment we pulled into the drive we fell in love with this little quaint cabin. It is right on the water and wonderfull views from all over. The cabin was spanky clean in every aspect, with a well stocked kitchen. My only suggestion would maybe put a large umbrella on the deck but I can understand that ir could be a problem if people left it up while gone. I can promise you we will be bck next year!" - "The property was immaculate & well equipped. Exceptional views from sunrise to sunset. Comfy bed. Perfect holiday."

This is a newly renovated home, with a nice size kitchen with everything you made need for preparing your meals. Children under the age of 17 are free to stay.
A large living room to relax and the t.v. Is cable ready and we offer Netflix also.
There are 2 bedrooms with a queen size bed in each. We provide all the linens and towels.
There is a full bathroom with a tub.
There is a deck attached to the house for relaxing.
Here is a propane fire pit for your own personal use.
Enjoy the large yard and private parking. It is wheelchair accessible.
There are many local walking paths. Enjoy watching the fisherman leaving the bay to get their daily catch. Bald and golden eagles are a pleasure to watch flying overhead.
There is a propane fire pit to enjoy while sitting outside.
Many local attractions to see. Go kayaking right out front of the house. Enjoy fishing and/or swimming off the dock just out front of the house. There is a private deck attached to the house. The nearest town is Brunswick.

- "We loved the view! The hosts were very quick to respond to any questions. This is a lovely spot to relax and watch the sea." - "After 6 days is crowded Bar Harbor, this was a perfect spot to relax. The weather was perfect, the views were great and the house had everything we needed." - "We sincerely enjoyed our stay. A very nice and clean place with many amenities. What a great place to relax, wet a line, and forget about the world."

Located in Harpswell!!!
ANOTHER DAY IN PARADISE!!!! Surrounded by 300 acres of pristine land in Harpswell Maine sits a west facing home tucked away beneath 60 foot pine trees. Watch time slow down as you sit on a deck, in the gardens or sunroom watching the lobstermen and clammers out front, or take walks thru the Austin Carey Wildlife Trails. Enjoy a one floor ranch style home, 2 bedroom 2 full-baths, attached garage and mudroom with washer and dryer, full kitchen and dining room, living room with bay windows and sliding glass door all facing the rock bound coast of Maine. Wake up each morning to watch the herons, egrets and other waterfowl dine out front. Drive to nearby islands, visit Land's End on Baileys Island and enjoy lobster dinners at nearby restaurants. Visit Bowdoin College in historic Brunswick Maine and everyone;s favorite, LLBean! Enjoy Maine State Theater performances, the Harriet Beecher Stowe home, visit Bath Maritime Museum, Coastal Maine Botanical Gardens and Camden is just up the road!!! and much much more!!

- "wonderful view of the water. lots of hiking in the area. good lobsters close by yet very secluded for a peaceful vacation. Harpswell is a beautiful area." - "We thoroughly enjoyed our stay. Nancy was so welcoming and we so enjoyed our conversations. The house is very comfortable and peaceful, it’s all on one floor. Sitting on the deck in the evenings, overlooking the water of Long Reach inlet you can “hear” the silence and watch the sunset. Beautiful view of the water as well from the living room and the sunroom. Her flower gardens bring a smile to your face. A great place to go to get away from the day to day rush."

Never feel hot in summer in this beautiful and large ocean front studio.(over 1000 square feet) natural ocean breeze crossing through every window, and you can watch sun rise every mornings. Private dock equipped with boats and kayaks so you can go boating, lobstering, clamming, or just laying down under the sun and watch seagulls and duck swimming by. This property is nicely furnished with a full kitchen, everything you need is provided to make sure you enjoy your wonderful stay.

- "This home is in a beautiful and convenient spot. This spot is idyllic for relaxing, reading your book or just enjoying nature. I got to see lots of fish as well as seals. The hosts are incredibly gracious and very helpful with everything we needed. Perfect spot and well worth the stay." - "Property managers were very welcoming and helpful. The place was beautiful right on the water with windows all around. we enjoyed our stay" - "This is a new listing and we were fortunate to be the very first guests! Do not hesitate booking this incredible property because there aren’t a lot of reviews- it IS everything you see in the photos and more! The hosts were very helpful and over the top kind! It was very clean and we had everything we needed. I loved all of the windows that wrapped around the boathouse- we had cool ocean breezes and the most incredible sunrises you’ve ever seen! We especially enjoyed the dock- a great place to relax, fish (super fun), or take the kayaks out and enjoy a peaceful paddle in the beautiful bay. Adult and child life jackets were also supplied. We saw many types of birds including Osprey, gulls, blue heron, cranes, pipers and more and had a seal that entertained us our last day! The location is perfect for anything you want to do. Not far from Portland, close to the cute shops in Brunswick, and a short distance to breathtaking Orr’s & Bailey’s Islands. There are many places to explore. We highly recommend visiting The Giant’s Stairs and shopping at Land’s End Gift Store. Favorite restaurants: Iris Eats Maine (Good for you food!!), Sundrenched (best Haddock I’ve ever had!!) and of course Little Tokyo in Brunswick, owned by the hosts - excellent cuisine & service! We loved the boathouse so much, we stayed an extra day! It was hard to leave this little slice of heaven… but we’ll definitely go back. You will LOVE your stay & you will love the hosts! Don’t hesitate- book now!"

Located at the edge of Gun Point Cove, The Studio, is a rare property. The highest tides flow under the deck and from the living room, you are sitting eye-level to lobstermen hauling their traps just yards away. Unrestricted and spectacular 270 degree views of bustling Casco Bay. This is the perfect get-away where a weary soul can rejuvenate and be inspired by Nature’s best.
The secluded pebble beach just a few steps away, is the ultimate for searching for sea glass and contains a large tidal pool where squid, fish, lobsters and crabs can usually be found by brave individuals willing to wade into the knee-deep cool sea water.
Moonlit nights are absolutely breathtaking. With none of the typical city-light pollution, the true colors of the night shine through and the moon light reflects vividly off a jet-black shimmering mirror.
This property is perfect for two, but accommodates four. It is the little sister to The Point (Vrbo 683109) located nearby. Both properties share a solar-heated saltwater swimming pool which is located between the cottages.

- "The pictures do not do this cottage justice. It is serene, and you are literally on the water. The property manager was extremely helpful and communicative. Also I've never seen a cleaner rental and I am an OCD cleaner. Thank you for the relaxation and the ability to be so close to nature." - "My husband and I had a fantastic time during our stay @ the Studio. We enjoyed the stunning views from our porch, exploring on the beach at both low and high tide, watching the lobster boats and soaking up the sun while relaxing on the porch. There were plenty of towns nearby for shopping for necessities and dining. We had a wonderful vacation."

Welcome to Drake!

Looking for a romantic couple's getaway? This charming, newly remodeled one-bedroom cottage is located in the heart of Cundy's Harbor. Enjoy your morning coffee on the deck, that sits right over the water, while watching the lobstermen head out for their day.

Upon entering this adorable, quaint cottage you will first notice it's open concept living/kitchen area. The kitchen appliances are all smaller, including the fridge, but you can still utilize them for all your cooking needs. The bathroom is located on the first level and has a stand up shower. The sliding glass doors lead you right to the deck that sits out over the water. Upstairs you will find a large sized bedroom with a king size bed and beautiful ocean views.

*Note- the parking for the cottage is across the lawn.

- "Our week at Drake cottage was beautiful, relaxing and much too short! The space and amenities are just right for two and exactly as advertised – the cottage and the location are just about as perfect as it gets. Time spent on the deck was a joy and the spaces inside, upstairs and down, managed to be both cozy and airy at the same time. The cottage was impeccably clean and outfitted, and Your Island Connection was consistently and immediately available if needed. We brought our sea kayaks with us and there was ample room to park the trailer and launching access was a very short carry down the end of the road. It was a wonderful week, and we are already planning and so looking forward to our next visit!"