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

Home in Dover

4.98 out of 5 average rating, 42 reviews

Modern 3-Story Cabin! Ski-on/Ski-off, Hot Tub & EV

Slopeside Rd! Perfect for Skiing, Hiking, Biking, Foliage, or Carinthia Base Lodge Events! Our newly renovated 2300 sq ft family-friendly Mt Snow retreat (4 bedrooms - King, 2 Queens, 4 Twins - 2 kitchens, 2 family rooms, brand new hot tub, and EV charger) is a memorable getaway home for any season! Skiers can walk out the front door with skis and be on the slopes (or great hiking) in seconds. Seconds to Carinthia and short stroll/ski to the main base of Mt. Snow. FYI Instacart delivers here!

Guest favorite

Cabin in Wilmington

5 out of 5 average rating, 65 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 the place to be for morning sunrise & coffee Located in Chimney Hill, includes outdoor & indoor pool, gym, tennis, basketball cts. Harriman Reservoir & Lake Raponda for kayaking/ swimming & Wilmington restaurants & shopping are close by. The home is pet free & has high speed fiber! Insta @bearlairlodge

Guest favorite

Villa in Pownal

4.93 out of 5 average rating, 60 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

Condo in Stratton

5 out of 5 average rating, 10 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

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

Apartment in Williamstown

5 out of 5 average rating, 115 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

Cottage in Westminster

5 out of 5 average rating, 55 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.

Guest favorite

Townhouse in Dover

4.94 out of 5 average rating, 16 reviews

New! Mt Snow Condo. Walk to lifts, pool, Hot tub

This completely renovated unit is the perfect opportunity for a small family looking to experience the beauty and excitement of mountain life! Enjoy the convenience of walking distance to the ski slopes and the comfort of an indoor heated pool and tennis courts at your fingertips. Plus, it's just minutes away from the lake and picturesque hiking in the summer and fall.

Guest favorite

Home in Newbury

5 out of 5 average rating, 13 reviews

Nature, comfort, & large tiled hot tub

Sitting at 1,100 feet above sea level, on 32 acres, bask in the fresh mountain air at this unique and family-friendly place. Relax with an oversized stone and tile hot tub with a waterfall. 7 minute drive to skiing at Mt. Sunapee. Minutes to various trailheads. Wilderness and wildlife abound. Bring your family and friends to this unforgettable location.