Best Accommodations in Winchester

A recently renovated vacation home, Storybook Lake Front Villa with Private Beach! offers accommodations in Winchester. This beachfront property offers access to a patio, free private parking, and free Wifi. Outdoor seating is also available at the vacation home. Featuring a balcony with lake views, this vacation home also includes a flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 1 bathroom with a shower and a hair dryer. The vacation home offers bed linen, towels, and laundry service. Guests at Storybook Lake Front Villa with Private Beach! will be able to enjoy activities in and around Winchester, like fishing, canoeing, and hiking. An indoor play area is also available at the accommodation, while guests can also relax in the garden. Fort Dummer State Park is 18 miles from Storybook Lake Front Villa with Private Beach!. Worcester Regional Airport is 55 miles from the property.

Internet • Balcony/Terrace • Pet Friendly • Security/Safety • Sports/Activities • Laundry • Parking • Other • Barbecue/Outdoor Cooking • Child Friendly • Oceanfront • View

Bed & breakfast in West Chesterfield with free breakfast and a restaurant
This smoke-free bed & breakfast features a restaurant, a bar/lounge, and conference space. Free cooked-to-order breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, concierge services, a library, and express check-in are onsite.
Chesterfield Inn offers 15 air-conditioned accommodations with DVD players and minibars. Pillowtop beds feature premium bedding. Flat-screen televisions come with satellite channels. Bathrooms include shower/tub combinations, bathrobes, designer toiletries, and complimentary toiletries.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and phones. Additionally, rooms include hair dryers and irons/ironing boards. Housekeeping is offered daily and in-room massages can be requested.

- "We came just for a night and loved it. The place was clean and cozy. The food was amazing. They even made us a gluten free breakfast which is so great! Thank you so much 💜" - "This is a genuine five star property, an ideal of what a country inn should be. Beautifully designed and decorated, comfortable and welcoming, charming staff. One of the nicest places we’ve ever stayed." - "Great stay" - "Lots of things were lovely; fantastic room service food (unbelievably fresh and delicious, better than anywhere I’ve ever eaten in a hotel while traveling), beautiful serene natural setting, and wonderful design of the buildings plus COOKIES and tea in the afternoon. The service was also fantastic. The paint could use freshening and the bathroom grout needs redoing (or consider retiling). A piece of one window pane, a wood bit, fell off… so I stuck it back, obviously needs a proper repair. With minor refurbishment, this establishment could be exquisite. Also, New Hampshire or Vermont local bath products would be preferable to English imports. Other things that made this a lovely place to visit was Yoda the tuxedo cat, the reclaimed barn main building, the lovely fireplaces, the proximity to Brattleboro and Keene, the pond and surrounding area, and the very amiable and kind, friendly staff. "

Picturesque Lakefront Retreat at Spofford Lake, Sleeps 10 is located in Chesterfield, just 18 miles from Santa's Land USA and 25 miles from Molly Stark State Park. The air-conditioned accommodation is 13 miles from Fort Dummer State Park. With free Wifi, this 2-bedroom vacation home provides a cable TV, a washing machine, and a fully equipped kitchen with a microwave and fridge. Towels and bed linen are provided in the vacation home. The accommodation has a fireplace. Bellows Falls Amtrak Station is 28 miles from the vacation home, while Mount Snow Resort is 30 miles away. Worcester Regional Airport is 64 miles from the property.

Internet • Air Conditioner • Fireplace/Heating • Child Friendly • Security/Safety • Parking

Riverfront bed & breakfast with free breakfast and a 24-hour business center
Along with a bar/lounge, this smoke-free bed & breakfast has a 24-hour business center and spa services. Free full breakfast is provided, as well as free WiFi in public areas, free self parking, and free train station pick-up. Additionally, concierge services, a computer station, and a library are onsite.
Inn on Putney Road offers 6 accommodations with DVD players and complimentary bottled water. Each accommodation is individually furnished and decorated. Flat-screen televisions come with cable channels. Bathrooms include shower/tub combinations, bathrobes, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and desk chairs. Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

- "A lovely four day stay in Vermont. Inn was perfect, with gardens to enjoy and lots of lounges and nooks to spend time and read. We had a suite with a separate sitting room, which allowed us to have our daughter accompany us on a last minute visit. Paul and his staff are super accommodating and are genuinely friendly hosts. Paul also cooks all the breakfasts which are superb! Different breakfasts each day, beautifully presented and absolutely delicious!"

Rustic-Chic Cottage with Yard and Grill - Near Hiking! offers accommodations in Northfield, 25 miles from East Village Historic District and 27 miles from Hampshire College. The air-conditioned accommodation is 24 miles from Beneski Museum of Natural History. Free Wifi is available throughout the property and Amherst College is 24 miles away. Providing a patio with garden views, this vacation home also offers a flat-screen TV, a well-equipped kitchen with an oven, a microwave, and a toaster, as well as 1 bathroom with a bath and a hair dryer. The property has an outdoor dining area. Guests can also relax in the garden. Pelham Town Hall Historic District is 28 miles from the vacation home, while Fort Dummer State Park is 20 miles away. Worcester Regional Airport is 49 miles from the property.

- "Perfect for rest and relaxation in a private park like garden setting." - "I would return even if I had no reason to be in that area!!" - "Great place, great location!" - "Excellent" - "Magical little place - close to lots of activities."

Colonial bed & breakfast in Northfield with free breakfast
A microwave in a common area, a refrigerator in a common area, and a library are available at this smoke-free bed & breakfast. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, tour/ticket assistance, wedding services, and a garden are onsite.
Housekeeping is available once per stay.
Centennial House offers 5 air-conditioned accommodations with hair dryers and complimentary toiletries. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Televisions come with cable channels.

Bathrooms include bathtubs or showers. Guests can surf the web using the complimentary wired and wireless Internet access. Housekeeping is provided once per stay.

- "We had a wonderful stay while visiting our family here in Northfield. Joan and Steve have such a charming home and we were delighted and grateful to wake up to an amazing breakfast. Lucy the pup was an extra bonus and the only thing I regret is not getting more pets in. Looking forward to more stays in the future!" - "What a lovely stay. The food was delicious and the hosts were so kind. " - "Loved our stay" - "The room was exceptionally clean and cozy. Lucy the pet dog so sweet and friendly! We enjoyed conversing with Steve and Joan."

Quaint Massachusetts Home with Yard and Grill! offers accommodations in Gill, 29 miles from Amherst College and 28 miles from Beneski Museum of Natural History. Complimentary Wifi is available throughout the property and private parking is available on site. The property features a 24-hour front desk. The vacation home features 2 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with a hair dryer. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. East Village Historic District is 28 miles from Quaint Massachusetts Home with Yard and Grill!, while Fort Dummer State Park is 16 miles from the property. Worcester Regional Airport is 53 miles away.

- "It was great" - "First Air b& b stay with my family. Was hesitant but would now think about doing again" - "Quiet, country location."

Bed & breakfast in Keene with free breakfast
A garden, barbecue grills, and free breakfast are available at this smoke-free bed & breakfast. Free WiFi in public areas and free self parking are also provided.
Housekeeping is available on request.
The Carriage Barn Inn offers 4 accommodations with air conditioning. This Keene bed & breakfast provides complimentary wireless Internet access.

Bathrooms include shower/tub combinations. Business-friendly amenities include phones; local and long-distance calls are complimentary (restrictions may apply). Housekeeping is offered on request and irons/ironing boards can be requested.

- "Great location. Easy accessibility to everything. Owner, Will was a delight!" - "Owner is very personable. We enjoyed talking to Joe and learning about the history of the house. Location was great and we were easily able to walk downtown." - "Wonderful host, beautiful facility, quiet and beautiful setting. Highly recommend. " - "Loved the property. Beautiful old house!" - "The property was very clean and comfortable, and we enjoyed meeting our host Joe and talking with him. We would stay here again if we return to Keene."

Featuring garden views, The Tartan Fox at the Meadmere in Swanzey provides accommodations, massage services, and a garden. Housed in a building dating back to 19th century, this bed and breakfast is 25 miles from Fort Dummer State Park and 26 miles from Bellows Falls Amtrak Station. The bed and breakfast features rooms with air conditioning, free private parking, and free Wifi. All units come with a seating area, a TV with cable channels, and a private bathroom with a hair dryer and shower. Rooms are fitted with a coffee machine, while some have a patio. At the bed and breakfast, units are fitted with bed linen and towels. Full English/Irish and vegetarian breakfast options with warm dishes, fresh pastries, and fruit are available. The bed and breakfast also comes with outdoor fireplace and a picnic area for a day outdoors. Santa's Land USA is 28 miles from the bed and breakfast. Worcester Regional Airport is 55 miles from the property.

Wellness Facilities • Balcony/Terrace • Internet • Security/Safety • Sports/Activities • View • Parking • Accessibility • Fireplace/Heating • Air Conditioner • Other • Guest Services

Traveling professionals take note; this unit has it all! Beautiful two bedroom in Victorian style that can be found throughout with some truly unique features. Hardwood floors. Sunlight drenches the unit throughout the day so much so that you will find yourself rarely turning on a light! Thoughtfully appointed furniture to include comfortable beds in each bedroom. Two heat pumps provide AC for those rare hot Vermont summer days. Propane cooking. All utilities included in rent; heat, Wifi, snow removal. Washer/dryer is provided in the basement. Dedicated off street parking for two cars. Best part - seconds walk to all that downtown has to offer! Food, art, fun! What's Gallery Walk? Come find out! Its what makes Brattleboro a one of a kind place to visit and live! -Walk to the Retreat, AMTRAK station with daily direct service to Burlington and NYC
-Minutes drive to area hospitals, SIT, Keene NH and Greenfield MA
For more information, visit our website at
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60 day minimum
Pets welcome - $100/month pet fee does apply

Pet Friendly • Tv • Internet • Other • Security/Safety • Bedding/Linens • Laundry • Fireplace/Heating • Air Conditioner • Kitchen • Wellness Facilities • Balcony/Terrace

Lakefront Orange Vacation Rental - Pet Friendly! is located in Orange, just 29 miles from Amherst College and 22 miles from Pelham Town Hall Historic District. The property is around 27 miles from East Village Historic District, 28 miles from Beneski Museum of Natural History, and 27 miles from Athletic Fields North. The property provides a 24-hour front desk and free Wifi is available throughout the property. Featuring lake views, the spacious apartment is composed of 1 bedroom and 1 bathroom with a hair dryer and free toiletries. Towels and bed linen are featured in the apartment. The accommodation has a fireplace. If you'd prefer to cook in the comfort of your own space, you can make use of the kitchen facilities, which include an oven, coffee machine, and a microwave. Emily Dickinson Museum is 28 miles from the apartment, while Amherst College Museum of Natural History is 28 miles away. Worcester Regional Airport is 37 miles from the property.

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

Bed & breakfast with free breakfast, 6-minute walk to River Gallery School
Along with coffee/tea in a common area, this smoke-free bed & breakfast has a library and a communal living room. Free full breakfast, free WiFi in public areas, and free self parking are also provided.
Private bathrooms are not ensuite and housekeeping is available on request.
The One Cat B&B offers 2 accommodations with DVD players and coffee/tea makers. These individually decorated and furnished accommodations have separate sitting areas. 31-inch LCD televisions come with premium digital channels.

Rooms have detached private bathrooms. Bathrooms include complimentary toiletries and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and ceiling fans. Change of towels and change of bedsheets can be requested. Housekeeping is provided on request.

- "Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!" - "Perfect location near downtown Brattleboro. Convenient, easy walk to shops, restaurants, museums. Pat and Conrad were warm, welcoming hosts. Conrad's homemade bread was delicious. I'm returning in October for his homemade English muffins and for some leaf peeping in the Green Mountains and the White Mountains just across the river. My room was very comfortable, with a comfy loveseat tucked under the corner windows for a perfect reading nook and what was probably the most comfortable bed I've ever slept in."

Deck, Mountain Views Colorful Retreat in Vernon! is located in Vernon, just 10 miles from Fort Dummer State Park and 25 miles from Santa's Land USA. Free Wifi is available throughout the property and Beneski Museum of Natural History is 31 miles away. The air-conditioned apartment consists of 2 bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a shower and a hair dryer. Towels and bed linen are available in the apartment. For added privacy, the accommodation features a private entrance. Molly Stark State Park is 26 miles from the apartment, while Athletic Fields North is 29 miles from the property. Worcester Regional Airport is 58 miles away.

Accessibility • Parking • Other • Guest Services • Security/Safety • Internet • Child Friendly

'The Gate House' aka 'Feathered Nest' | Fire Pit | Close to I-91 | WiFi

Book your next couple’s getaway or solo retreat at this 1-bathroom Vernon studio! Nestled on 7 acres, this vacation rental features a bright, charming interior, a well-stocked kitchenette, and a private outdoor space with a fire pit. When you’re not exploring the on-site trails, visit the sugar houses in Brattleboro or shred the slopes at a nearby resort!

-- THE PROPERTY --

MRT-11153470-001

SLEEPING ARRANGEMENTS
- Studio: 1 queen bed

MAIN FEATURES
- Dining counter
- Wood-burning fire pit

OUTDOOR LIVING
- Wood-burning fire pit
- Hiking & snowshoe trail access on-site

KITCHENETTE
- 2-burner stove, refrigerator
- Dishware/flatware, cooking basics, spices
- Drip coffee maker, electric kettle
- Microwave, toaster oven

GENERAL
- Free WiFi
- Keyless entry
- Linens/towels
- A/C & heat pump

FAQ
- Wood-burning stove unavailable

ACCESSIBILITY
- Single-story studio, stone path & 3 steps to enter

PARKING
- Gravel driveway (2 vehicles)

ADDT’L ACCOMMODATIONS
- An additional property is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking

-- THE LOCATION --

- Direct access to 5,000 acres of hiking & snowshoe trails
- Near multiple ski resorts
- 0.1 miles to Tiny Bread Box
- 2 miles to Vernon Recreation Center - seasonal pool (w/ fee), tennis courts, pickleball, driving range, basketball
- 10 miles to Brattleboro - shops, restaurants, breweries, Vermont sugar houses
- 100 miles to Manchester-Boston Regional Airport

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome--because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in

ADDITIONAL INFORMATION
- The wood-burning stove is not available for guest use
- This single-story studio requires a stone path and 3 steps to enter
- There is another bookable vacation rental located on-site, in the next-door property with a separate entrance, that shares the outdoor areas; other travelers may be present during your stay

- "Excellent little cozy cabin perfect for me. Kitchen was well stocked with what I needed for small meals made. Bed and bathroom excellent. Was able to enjoy a woods walk in the nearby town forest. Will be back soon. Wanted to add an extra day and that was accommodated with ease." - "What an amazing little cabin! It had everything I needed and was so well kept and beautifully decorated. I will tell others about it and I will be back again. "

Historic Home with Modern Updates on Less Than 4 Acres offers accommodations in Royalston, 23 miles from Pelham Town Hall Historic District and 29 miles from East Village Historic District. This vacation home offers accommodations with a patio. Free Wifi is available throughout the property and Amherst College is 30 miles away. The air-conditioned vacation home consists of 4 bedrooms, 3 living rooms, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a shower and a hair dryer. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. Beneski Museum of Natural History is 30 miles from the vacation home, while Athletic Fields North is 29 miles away. Worcester Regional Airport is 39 miles from the property.

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

This fully furnished two bedroom apartment features light filled rooms with plenty of space to work or stretch out and relax. Excellent high speed wifi. You will find a stocked kitchen that provides everything you need to live comfortably while away from home, or perhaps this is your new home? Thoughtfully appointed furniture can be found throughout which puts the emphasis in this warm and welcoming space. Everything is included in in rent; heat, electric, high speed wifi, use of shared W/D, off street parking and snow removal from the driveway.

Kitchen • Child Friendly • Wellness Facilities • Internet • Security/Safety • Fireplace/Heating • Air Conditioner • Pet Friendly • Bedding/Linens • Laundry

The Zen Waterfront Retreat: A Sweetwater Stay is located in Orange, just 28 miles from Amherst College and 21 miles from Pelham Town Hall Historic District. The vacation home features both Wifi and private parking free of charge. East Village Historic District is 27 miles from the vacation home and Beneski Museum of Natural History is 28 miles away. The vacation home consists of 3 separate bedrooms, 3 bathrooms, and 2 living rooms. The accommodation is non-smoking. Guests at The Zen Waterfront Retreat: A Sweetwater Stay will be able to enjoy activities in and around Orange, like fishing and canoeing. Athletic Fields North is 27 miles from the accommodation, while Emily Dickinson Museum is 28 miles away. Worcester Regional Airport is 38 miles from the property.

Guest Services • Security/Safety • Balcony/Terrace • Air Conditioner • Parking • Pet Friendly • Child Friendly • Internet • Other • Sports/Activities

New Hampshire Meals & Rentals Operator's License #063697
We only rent to mature adults aged 25 and older. No children allowed under 8 years old.
Private beach, dock, raft, rowboat, canoe, 5 Kayaks, or launch your boat. ROKU TV, high speed internet, WIFI, 42' flat screen internet TV.
Sleeps 6 - two bedrooms - One with Queen bed, one with two single beds (Can be made into a Queen), and a full-size pullout couch in the
family/living room.
106 feet of sandy beach with dock and raft for your swimming, boating, or fishing pleasure.
8' sliding door to patio 80 feet from water's edge.
Central air conditioning
Faces east for beautiful sunrises. Beach is sunny all day.
Eight golf courses are in the region.
Everything provided except beach towels.
Activities - swimming, fishing, boating, hiking, mountain climbing, golf, miniature golf, go carts, bowling, shopping, restaurants, plays, auctions, antiquing, Ice Fishing, Ice Skating, Snowmobiling, Cross Country Skiing, 1 hr. to Snow Skiing - Okemo - Mount Snow - Crotched Mountain.

The best of New England awaits you. A quaint New England town with baked bean suppers, antique shops & auctions, fairs and friendly people all nestled in the foothills of New Hampshire. Enjoy your weekends and vacations with deer, fox, Bald Eagles, and Canadian geese as life slows down to a relaxed pace. Four miles from New Hampshire's largest wilderness state park - Pisgah State Park. It's great for hiking and enjoying the great outdoors. Twenty-four miles to Mount Monadnock - Elevation 3,125' - One of the most frequently climbed mountains in the world.

- Most people are having such a great time - They don't leave the lake.

This abode is located on Forest Lake in Winchester, NH. The Monadnock Region is great for Summertime fun, Fall foliage, Winter activities or Springtime hiking.
- Handicap accessible - No stairs to climb or hills to navigate. 80 feet from the water's edge.
- No running up and down stairs with food plates, etc. The patio and barbecue grill are right outside your sliding door.
- Beach is sunny all day from sunrise to sunset - Some beaches are shady most of the day.
- Equipment provided - Canoe, rowboat, 5 kayaks, life vests
- We do have a dog on the premises. Her name is Lady Callie. She is very friendly and loves everyone.

2 hrs. from Boston, MA (90 mi.)
1 hr. 20 min. from Hartford, CT (85 mi.)
2 hrs. from Albany, NY (100 mi.)
3 hrs. from NYC (200 mi.)

- "Bill felt like my uncle, he was so kind and welcoming! And the doggo, Lady Cassie made our days bright with cuddles and pats like she was an old friend! The view of the lake and the leaves reflecting on the water was magical!! I can't wait to come back when it's warmer and take advantage of the kayaks!!" - "the property was even better than the pictures shown on VRBO. everything was spotless,everything you could ever want was included . there were kayaks, canoe,rowboat,fire pit all in like new condition. brand new kitchen and bath we hope to go again soon. PS.fishing was great also"

Walk to Trails Artsy Mtn-View Getaway in Vernon! offers accommodations in Vernon, 10 miles from Fort Dummer State Park and 25 miles from Santa's Land USA. This apartment features accommodations with a patio. Free Wifi is available throughout the property and Beneski Museum of Natural History is 31 miles away. The air-conditioned apartment consists of 1 bedroom, a living room, a fully equipped kitchen with an oven and a coffee machine, and 1 bathroom with a shower and a hair dryer. Towels and bed linen are offered in the apartment. For added privacy, the accommodation features a private entrance. Molly Stark State Park is 26 miles from the apartment, while Athletic Fields North is 29 miles from the property. Worcester Regional Airport is 58 miles away.

Accessibility • Internet • Fireplace/Heating • Guest Services • Parking • Child Friendly • Security/Safety • Other

Close to Northfield Mount Hermon School, The Gill Tavern, The Farm Table & Kringle Candle, Crumpler Fox Golf Course. You'll love this place because of the ambiance, privacy, the setting & the view. This place is great for couples, solo adventures, and business travelers.
In accordance with CDC guidelines we disinfect.
For guests who intend to work from home here or who like to stream, we upgraded our WiFi Extender to Tri-Band - giving super-fast speeds up to 2.2 Gbps

A 900 square foot space, with pull down queen Murphy bed. The mattress is very comfortable. The apartment has a living area, gallery kitchen, and bathroom with shower, vanity unit and toilet. Off the apartment is a 200 square foot deck, raised with a beautiful view of the trees and the Leyden hills beyond. The deck is private.

Guest access
Our apartment is self contained. It has its own entrance, and its own deck for your private use. The apartment is adjacent to our house, but the view from each deck does not look out at the other deck.

Other things to note
Hickory Hill Treetop Apartment is owned by the proprietors of Hickory Hills Pet Resort. The apartment sits well back from the facility. During the day there will be occasional noise from barking dogs.

- "Had a great, comfortable, clean, and easy stay!" - "The space worked for me and the hosts were very accommodating. Thank you. :-)" - "It's such a beautiful, private location and the place was very spacious and super clean. It had everything we needed, and the view was spectacular. Communication was great, and check in was easy. We could hear the pups a little, but it wasn't disruptive. Look forward to returning! Thank you so much for a great stay"