Holiday houses in Orange

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Top-rated holiday rentals in Orange

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

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Superhost

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

Home in Hoosick Falls

4.87 out of 5 average rating, 15 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! ☺

Superhost

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!

Superhost

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.

Superhost

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!

Superhost

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!

Superhost

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!

Superhost

Apartment in Williamstown

5 out of 5 average rating, 126 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.

Superhost

Home in Dover

5 out of 5 average rating, 5 reviews

Riverside Home On Route 100 (Moover Bus Stop)

Come stay at our newly renovated VT Route 100 getaway on the Deerfield River. We’re passionate about creating simple, thoughtfully designed homey spaces that make for the perfect retreat to Mount Snow. Located on the Moover route, just north of Snow Republic Brewery and next to High Altitude Ski Rental, this no-stairs unit offers convenience and charm in equal measure.

Superhost

Home in Great Barrington

5 out of 5 average rating, 6 reviews

Summer & Leaf Season Rental!

Charming, cozy cottage, walking distance to Lake Mansfield and Main Street attractions, 20 minutes to Tanglewood, 15 minutes to area summer camps or the Zipline at Catamount Ski Area. Freshly renovated throughout, fully-equipped kitchen, large yard with screened dining porch. Comfortable and stylish home in a centrally-located spot. Attention to all the little details.

Superhost

Townhouse in Dover

4.84 out of 5 average rating, 25 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.