Vacation rentals in Cheshire

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Top-rated vacation rentals in Cheshire

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Guest favorite

Home in Wilmington

5 out of 5 average rating, 10 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 well-maintained entryway showcases wooden steps leading up to the front door, accompanied by a railing featuring horizontal cable wiring. Lush greenery and colorful flowers are planted alongside the steps, enhancing the welcoming approach to the home.

Home in Hoosick Falls

4.85 out of 5 average rating, 13 reviews

Enjoy Fall & Experience Beautiful Changing Colors

Nestled on a private 5 acres lot on the border of NY and Vermont this home is just perfect. Just 30-60 minutes from several ski areas. This charming home has everything you need to relax and enjoy . The night sky perfect for stargazing. Have morning coffee on the deck and watch as deer wander in the fields or the cows across the meadow. Enjoy a quiet evening by the fire after a long day on the slopes or soak in the oversize soaking tub! Stroller, changing table and a pack-n-play included.

Superhost

Home in Readsboro

4.86 out of 5 average rating, 125 reviews

Beautiful Vermont! (Pet Friendly)

Our home is nestled in the Green mtns, with quick access to the road. A babbling brook lulls you from the master bedroom, a clawfoot soaking tub, stocked house(this is our home we Airbnb when we're away working ).Hiking, antiques, shops, lakes, ski, snowboard, covered bridges, local inns, mountain views! Scenic roads, nearby Mt. Snow, VAST snowmobile trails, Mt.Greylock, Mass MOCA museum, N.Adams, MA, Berkshires. Bennington Wilmington. Great location! PEACEFUL & PERFECT Vermont getaway! ☺

Guest favorite

A spacious living area features a central brick fireplace surrounded by built-in bookshelves. Light-colored sofas are arranged around a glass coffee table on a patterned rug, with large windows providing natural light and views of the outdoors.

Home in Old Chatham

4.96 out of 5 average rating, 25 reviews

Post and Beam Hilltop Sanctuary

Enjoy the quiet countryside/mountain views from this breathtaking private hilltop getaway. Step into our stunning vaulted Post & Beam home with central fireplace, cozy loft and spacious open floor plan that features a full wall of windows/doors to the back wrap around deck that allows for an incredible indoor/outdoor living experience with friends and family. Take advantage of our fully stocked chefs kitchen, comfy beds complete with fresh linens/towels and each bedroom has its own full bath.

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 24 reviews

Luxury Redo: Hot Tub, Playroom, Sleeps 12

Creamery: Fully Renovated 5 Bedroom Home, sleeps 12 with large screened porch, outdoor patio with seating, sun umbrella, hot tub, fire pit and billiards! Amenities also include: Central AC, all new kitchen appliances, washer/dryer, 4 Smart tvs, fiber internet + good cell service, propane fireplace, blue stone outdoor patio with seating, billiards table, playroom, high quality linens included, Front porch with seating, superior central location: less than 10 to GB, less than 10 to Catamount!

Top guest favorite

An open door leads to a private balcony, where a serene tree offers shade. A large, relaxed dog rests on the balcony floor. Bright greenery is visible, enhancing the tranquil outdoor atmosphere.

Apartment in Wilmington

4.91 out of 5 average rating, 134 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.

Top guest favorite

A newly renovated kitchen features a spacious layout with wooden flooring and a ceiling adorned with wooden panels. White cabinetry and a contrasting black countertop create an elegant contrast. Pendant lighting hangs above a central island, while a window allows natural light to fill the room.

Apartment in Saratoga Springs

5 out of 5 average rating, 30 reviews

The 1825 Saratoga Getaway - 2 beds 1 bedrm 1 bath

Come and relax in this centrally-located, newly renovated gem that accommodates 4 and offers all there is to enjoy about Saratoga. Two blocks to Beekman St Arts District ✅ 10 min walk to downtown Saratoga ✅ 1.2 miles to the track ✅ 2.3 miles to SPAC ✅ Character & charm of an 1825 house ✅ Top notch hospitality ✅ Includes: 1. New kitchen 2. LR w/ new leather queen sleeper-sofa and electric fireplace 3. BR w/ new queen bed and closet 4. Brand new bathroom w/ rain or wand shower & washer/dryer

Guest favorite

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

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, 69 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

A quiet mountain home is softly illuminated against a backdrop of tall trees and freshly fallen snow, capturing a peaceful winter night. The surrounding landscape showcases a blanketed yard, providing a serene atmosphere for a cozy retreat.

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!

Top guest favorite

A serene outdoor deck features a centrally placed Solo Stove surrounded by five wooden Adirondack chairs. The scene captures a tranquil sunset with soft pink and orange hues reflecting off distant mountains and lush greenery.

Chalet in Craryville

5 out of 5 average rating, 13 reviews

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.

Top guest favorite

Two wooden Adirondack chairs face a small fire pit, surrounded by a serene wooded area. A picnic table is positioned nearby, with a stack of firewood to the side. The Green River flows gently in the background, framed by vibrant greenery.

Apartment in Williamstown

5 out of 5 average rating, 125 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.