Holiday houses in Winchester

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Top-rated holiday rentals in Winchester

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

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Guest favourite

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 favourite

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 favourite

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

Apartment in Dover

4.81 out of 5 average rating, 80 reviews

*Betimor North Apt.4 Newly renovated Mt. Snow

Keep it simple at this peaceful & centra location updated June 2023 Fully stocked kitchen & toothpaste, soaps, shampoo. Relax on the new couch & watch the flatscreen TV Centrally located with comfort & convenience. Dining, shopping all within walking distance. Wilmington is just minutes away Up the road is Mount Snow for skiing and snowboarding. Golf courses close by. Close to hiking trails Nice valley location with many events happening throughout the year. NO PETS allowed

Superhost

Holiday home in Dover

4.81 out of 5 average rating, 32 reviews

Walk to Mount Snow, Cozy, Clean and Comfortable

You can walk, drive or take the shuttle to the slopes. Our unit has some views of the mountain. We strive to give you a fresh, clean, and comfortable condo for that memorable winter getaways. On top of being so close to Mount Snow, you have a garden-level unit with a private deck, a fireplace with complimentary firewood, and a warm heated pool. Our condo will comfortably sleep up to 4 guests, and a full-size kitchen with all the pots and pans for you to cook a special meal.

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 favourite

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 favourite

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.

Superhost

Townhouse in Peru

4.68 out of 5 average rating, 19 reviews

The Best Vermont Has to Offer!

GET AWAY to where you will have the best of all worlds! Within minutes of our beautiful spacious townhouse, there’s skiing, hiking, biking, horseback riding, Bromley Mountain Adventure Park with their famous Alpine Slide, golf, fly fishing, and every other outdoor activity you can think of. Yet nearby, there are also high-end designer outlets, local craft stores, spas and phenomenal restaurants.

Guest favourite

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 favourite

Home in Peterborough

4.95 out of 5 average rating, 93 reviews

Hazelhurst Vacation House

"Hazelhurst" is fully renovated and beautifully decorated vacation rental house in a private setting is just 1/4 mile from downtown shops and restaurants. With three bedrooms, a modern kitchen and plenty of space to relax any time of year. NH Meals and Rooms License #044799