Waterfront vacation rentals in Bennington County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Bennington County

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

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Guest favorite

Chalet in Dover

4.98 out of 5 average rating, 94 reviews

Mountain Chalet: brook-hot tub-firepit-mins to ski

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow and Stratton, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best cuisine VT has to offer.

Superhost

Cabin in Wardsboro

4.86 out of 5 average rating, 103 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Guest favorite

Cabin in Rupert

4.99 out of 5 average rating, 90 reviews

Elegant & Rustic VT Cabin - A Peaceful Getaway.

Nestled on 10 hillside acres just outside the small town of West Rupert, our cabin offers a relaxing "get-away-from-it-all," yet is convenient to all that southern VT and eastern NY has to offer. Perfect for a romantic weekend with a special someone, a relaxing country vacation with family, or a fun retreat with good friends. 3 BRs (plus sleeping loft) and full bath. Hike, bike, ski, golf, fish, shop, swim, dine, antique, explore, etc...or just relax and do nothing. Make yourself at home!

Guest favorite

Home in Arlington

5 out of 5 average rating, 21 reviews

New Charming Waterfront Cottage Retreat

This charming Vermont cottage is nestled in the West Arlington Valley, surrounded by the Taconic Mountains and on the Battenkill River. With three private acres, it offers stunning river and mountain views, a cozy retreat with quintessential decor, and luxurious comfort. Enjoy a garden, private trails, and river access. Just 12 minutes from Manchester’s shops and dining, it's perfect for couples or small groups seeking a scenic and relaxing getaway. This special slice of Vermont can be yours.

Guest favorite

Tiny home in Whitingham

4.9 out of 5 average rating, 81 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.

Guest favorite

Home in Manchester

4.98 out of 5 average rating, 87 reviews

Private Riverfront Getaway with Mountain Views

Be close to everything Manchester has to offer while enjoying gorgeous views and total privacy in a comfortable home you will have all to yourself! The perfect getaway any time of year. Feels like you are away from it all, but just minutes from amazing hiking, skiing, shopping, dining, and entertainment! 5 minutes to town and Bromley is less than 10 min away. Stratton and Magic Mt are both less than 25 min drives. Hiking trails, kayaking, fly fishing, and more are all right in your backyard.

Guest favorite

Home in Dover

4.93 out of 5 average rating, 82 reviews

Cozy Riverfront Home, 1mi to Mt Snow, On Moover

The Riverhouse at Mount Snow is 1 mile from the mountain (2 min car ride) or take the FREE MOOver. NEW AC. This cozy cabin has open main floor plan and sleeps 6 comfortably with 3 bedrooms, 2 baths, den, living room with wood fireplace. Washer/dryer, gametable, yard games, gas grill, deck overlooking a river with a swimming hole, private firepit area, privacy fence. Easy in/out right off Rt 100 - Walk to restaurants/brewery. Mt. Views from the front porch/yard. 15 Mins from Lake Whittingham.

Guest favorite

Cabin in Woodford

4.94 out of 5 average rating, 100 reviews

Charming Cabin with 2 baths in the Green Mountains

A cozy cabin nestled high up in the green mountains. A perfect getaway on a quiet street. This home is located in between the towns of Bennington and Wilmington. Across the street from Prospect Mountain (cross-country skiing and snow shoeing) and about 25-30 minutes to Mount Snow (downhill skiing). Vast snowmobile trail in our backyard. Visit the quaint general store nearby or go hiking in Woodford National State Park. At 2,000 ft elevation, the stars are on stage when it's a clear night.

Superhost

Cottage in North Bennington

4.88 out of 5 average rating, 312 reviews

Romantic Private Vermont Cottage - Waterfront

Welcome to beautiful Southern VT! This is a private cottage located in Bennington, VT. The setting is picturesque, on a private lake with diverse wildlife, waterfall and covered bridge. Full kitchen, covered porch, loft bedroom and additional sofa bed. We provide every conceivable amenity for a comfortable stay. A unique retreat for a cozy and peaceful getaway. There is no other vacation property of this quality and character in southern Vermont. Enjoy mornings on your own private lake.

Guest favorite

Guesthouse in Manchester

4.97 out of 5 average rating, 74 reviews

On Bromley Brook

Beautifully detailed separate and private 2nd floor living space on the grounds of a 2 acre 1890's farmhouse. In season, enjoy morning coffee on the large deck overlooking the perennial garden or sit and read a book by the river. In winter take in the beautiful open view of Mt. Equinox. Walk to the center of town for shopping and dining in 10 minutes (0.8 miles). Bromley is 12 minutes away and Stratton is a 22 minute drive. We are nearby and are usually available if needed.

Guest favorite

Home in Londonderry

4.98 out of 5 average rating, 115 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

Guest favorite

Rental unit in Wilmington

4.98 out of 5 average rating, 464 reviews

**Happy Hour! Gorgeous & Modern Downtown Retreat**

Come enjoy our beautiful apartment above our liquor store in downtown Wilmington! Lots of local shops and dining right in town! We are along a river and next to a hiking trail system! Walking distance to the serene 10+ mile lake; kayaks, stand-up paddle boards or motor boat/jet ski rentals nearby. In the winter, enjoy local trails on snowshoes or cross-country skies; only 15 minutes to Mount Snow! We look forward to meeting you!!!