Vacation rentals in Shelburne

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Top-rated vacation rentals in Shelburne

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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-appointed kitchen is visible through an archway. White cabinetry and appliances contrast with the warm wood tones of the floor. A gas stove, microwave, and refrigerator provide modern amenities, while countertops offer ample space for meal preparation.

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 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! ☺

Top guest favorite

A spacious deck features several lounge chairs and a table, inviting relaxation. A bright red umbrella provides shade. The tranquil lake extends in the background, with a private dock visible along the shoreline, framed by lush greenery.

Home in Pittsfield

4.97 out of 5 average rating, 115 reviews

Berkshire Lake- Modern and Updated-close to skiing

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Guest favorite

Two blue Adirondack chairs are positioned on a wooden deck overlooking a lush green lawn and Sadawga Lake. A gas grill is situated nearby. Soft shadows are cast on the deck from the chairs, with the sky above featuring scattered clouds and sunlight.

Tiny home in Whitingham

4.91 out of 5 average rating, 98 reviews

Cozy Lakeside Tiny Home, Near Skiing

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. A perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. It's a quick drive to skiing at Mount Snow, shopping and dining in Wilmington, and direct access to the VAST trail.

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.

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

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, 124 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 spacious interior features warm wooden accents, including a large barn door that leads to another area. The dining table is positioned along one side, and a mirror reflects light from the softly illuminated ceiling. The open design connects to the kitchen area in the background.

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.