Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A two-story house is nestled in a snowy landscape, surrounded by bare trees. The exterior features a combination of beige and green, with large windows allowing for ample natural light. A covered deck with wooden beams and a patio area is visible in the foreground.

Home in Wilmington

5 out of 5 average rating, 8 reviews

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

Enjoy stunning lake & mountain views w/ easy access to hiking, swimming, boating, & fishing (kayaks, paddle board, and bikes included). Cathedral ceilings w/ beams provide a cozy feel & heated floors give an always-warm home in the winter. Covered deck w/ grill is great for outdoor dining. Additional features include outdoor hot tub, sauna, & quality game room (pool table, shuffleboard, foosball, ping pong). 4WD/AWD required in winter. Close to Mt. Snow & downtown Wilmington w/ shops and dining.

Superhost

A spacious room features two beds with floral-patterned bedding. Natural wood elements, including door frames and furniture, add a warm touch. Soft lighting is provided by a lamp on a small bedside table, while framed artwork adorns the walls.

Apartment in Pownal

5 out of 5 average rating, 8 reviews

"The Triple Chambers"

This beautiful, spacious, and historic property was formerly the Inn at Oak Hill. It is convenient to Williams College, Williamstown Theater Festival, Clark Art Museum, MassMOCA, FreshGrass Festival, BerkshireStock, Jiminy Peak, Bennington College, VAST snowmobile trails, and many other destinations in southern Vermont and western Massachusetts. Comfortably furnished with modern amenities such as Wi-Fi and satellite TV, our home also surrounds you with beautifully preserved & original features.

Guest favorite

A modern chalet sits surrounded by lush greenery, featuring a stunning wrap-around deck adorned with string lights. An inviting fire pit area with seating complements the spacious backyard, highlighting the connection between indoor comfort and natural beauty.

Cabin in Wilmington

5 out of 5 average rating, 69 reviews

Modern Chalet-private deck/firepit/ clubhouse pool

Nestled in the Green Mountains this custom modern chalet is the perfect location for your family vacation! Enjoy the peaceful tranquility, 12 min. from Mt Snow. The private wrap around deck is perfect for morning sunrise & coffee Located in Chimney Hill, with outdoor & indoor pool, gym, tennis cts. Harriman Reservoir & Lake Raponda for kayak/swimming & Wilmington restaurants, shopping and Golf are close by. The home is pet free & has high speed fiber! New EV Tesla charger Insta @Bearlairlodge

Guest favorite

A comfortable living area features a dark leather sofa with two accent pillows and a coffee table atop a patterned rug. A dining table with four chairs is positioned nearby, and natural light enters through a window dressed with light curtains. Wall decor includes vintage skis and decorative deer antlers.

Apartment in Wilmington

4.91 out of 5 average rating, 130 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Superhost

A modern townhouse features a striking facade with a mix of wooden shingles and large windows. Lush landscaping surrounds the entrance, which is approached by a stone pathway leading up to the front door. A clear blue sky adds to the inviting exterior.

Townhouse in Wilmington

4.87 out of 5 average rating, 15 reviews

VT Ski House - Great for Families and Groups!!!

Available for Christmas Week !! Perfect getaway!! 5 bedroom brand-new townhouse located at The Hermitage Club in beautiful southern Vt. Three master bedrooms, two children bedrooms with bunk beds. Modern kitchen. Upstairs and downstairs living rooms. Outdoor space. Walk in closets. Washer/Dryer. Brand New Green Egg Grill! Very short drive to Mt. Snow. Ski In- Ski Out for Hermitage Club Members! Located near fantastic hiking, mountain golf, world class fishing, the great outdoors!

Guest favorite

An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.

Villa in Pownal

4.94 out of 5 average rating, 67 reviews

Vermont Vacation Villa—Grapevine Getaway

Nestled in the stunning natural beauty of Vermont, this striking villa offers the perfect escape from the hustle and bustle of everyday life. Surrounded by rolling hills, and picturesque countryside, this home is a paradise. Whether exploring the area's cultural institutions, immersing yourself in the natural beauty of Vermont, or relaxing and unwinding with family and friends, this vacation home is the perfect retreat. Experience the magic of this beautiful area for yourself!

Guest favorite

The spacious living area features comfortable seating with a sectional couch and additional chairs. Natural light filters through large windows, illuminating the room. A dining area with barstools is visible in the background, along with charming decor that enhances the lodge-style ambiance.

Condo in Stratton

5 out of 5 average rating, 12 reviews

Top Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt

Rising Bear Duplex 411 at Stratton Mt-Seasonal Rental Available Spacious 3Br/4Bth Lodge on The Commons w/ Ice Skating Pond, Heated Pool, 2 Min Walk To Ski Family Friendly Spacious Lodge With Mountain Views, Excellent Location. Inspired by the great lodges, Rising Bear is located on the Commons, with ice skating, firepits and family activities. Convenient heated underground parking space and generous living spaces make Rising Bear ideal for bigger families and group gatherings.

Superhost

A sprawling grassy yard is surrounded by trees, providing natural shade. A wooden deck and seating area are positioned in the background, inviting outdoor relaxation. The white house is visible beyond the tree line, contributing to the serene countryside setting.

Home in Readsboro

4.86 out of 5 average rating, 125 reviews

December in Peaceful Vermont (Pet Friendly)

Country Home, nestled in the Green mountains, panoramic views, with access to the road. A babbling brook to lull you asleep from the master bedroom, a clawfoot soaking tub, stocked house. Hiking, antiques, shops, lakes, ski, snowboard, covered bridges, local inns, mountain views! Enjoy Vermont! Scenic roads, nearby Mt. Snow, VAST snowmobile trails, Mt.Greylock, Mass MOCA museum, N.Adams, MA, Berkshires. Bennington Wilmington. PEACEFUL & PERFECT Vermont getaway! ☺

Guest favorite

Home in Harrisville

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Guest favorite

The exterior of a spacious home is presented, featuring a light-colored facade and a welcoming red door. The surrounding area is partially covered in snow, with pine trees in the background and a fire pit area visible on the lawn.

Home in Wilmington

5 out of 5 average rating, 26 reviews

Kiki's Mountain Chateau

Refresh and reset within this spacious, serene space destined to be a memorable family retreat. A charming getaway with all the comforts of home with the best nature has to offer. Located in the small town of Wilmington and just a short scenic drive to Mount Snow. Local watersports, winter sports, nature trails, foliage, bird watching, stargazing and plenty of local charm. Kiki's has enough room for everyone to unwind or gather together. ***Hot Tub has arrived!

Guest favorite

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and oven. White cabinetry offers ample storage. A central island features a sink and prep space, complemented by a set of kitchen utensils. Natural light enters through a nearby window.

Apartment in Williamstown

5 out of 5 average rating, 119 reviews

Downtown | Waterfront | Walk to Shops

★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.

Guest favorite

A tranquil scene of a calm lake reflecting lush green trees and charming homes along the shoreline. A wooden dock provides access to the water, while kayaks rest on the bank, inviting exploration of the serene surroundings.

Cottage in Westminster

5 out of 5 average rating, 58 reviews

Cottage @ Partridge Pond

Relax on Partridge Pond. Great for paddle boarding and swimming or just hanging out on the deck/dock and grilling. Great local restaurants and Wachusetts brewery 5 min up the road and Wachusetts ski area 10 min away. Local hiking trails and golf course nearby. Newly furnished. Updated utilities. Quiet area and a great retreat. Year round entertainment. We enjoy our time here. This is a ‘pet-free’ property.