Waterfront vacation rentals in Bennington County

Condo in Manchester

Battenkill River Condo Home, South unit

Seasonal Rental Available for 12/1/23 to 4/1/24!!!! Inquire about it!!! Perfect location to everything Manchester has to offer! The property boasts peaceful views and access to the Battenkill River. While the setting is private and serene, within a few minute drive, you can be to shopping, dining, and hiking. Bromley-12 min! Stratton-25 min! Killington, Mt. Snow, and Okemo all within an hour's drive. No Pets allowed due to owner'sallergy. A separate rental agreement is required for all rentals

Nov 20 – 27

Cabin in Wardsboro

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.

Jan 13 – 20

Cottage in Woodford

Willow Tree Cottage on Peaceful Mountain Lake

Welcome to my romantic cottage on a serene mountain lake in the Green Mountains of Southern Vermont. Only a 3 hour drive from NYC, it's another world of peace, beauty, and tranquility. Nearby are the Appalachian Trail, National Forest, State Park, hiking and cross country ski trails, boating, fishing, and swimming, private dock, antiquing, restaurants, art museums, history, and theatre. This is a cultural and naturalist's wonderland. Recently fully renovated. Not suitable for young children.

Oct 19 – 26

Home in Wilmington

Find your escape at The Coldbrook House, Mt Snow

A beautifully-secluded modern ski home near Mt Snow with 500 feet of private access to the Cold Brook. Exceptionally furnished with custom wood flooring and stone fireplace, Subzero & Wolf appliances, walk-in shower with custom river rock flooring, pool table, shuffleboard, and 7-person hot tub. 10 min to Mount Snow, 30 to Stratton. 5 min to downtown Wilmington and Herriman Reservoir. Perfect for 3-4 families or couples trips. Come enjoy the beauty of Southern Vermont at The Coldbrook House!

Apr 4 – 11

Home in Jamaica

Stratton Spa House with Man Cave

MANAGED BY A 5 STAR TEAM WITH MULTIPLE 5 STAR HOMES Perched on a babbling brook this 4700 square ft. contemporary has all your needs covered. Smart tech, 3 fireplaces, man cave, streaming entertainment, home theater, spa suite, hot tub, sauna, pool table, darts, poker room, dueling xbox room, giant master suite, big guest suite with wood burning stove, large dining table, fully equipped kitchen, Keurig, screened porch, 3 private acres, sun deck, bbq, 1/4m walk to water falls and swimming hole.

Jun 6 – 13

Home in Manchester

Riverfront Getaway w/ Mt 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.

Nov 3 – 10

Apartment in Dover

Brookside Hideaway Retreat

Take it easy at this tranquil getaway in the heart of West Dover, Vermont. Located along the public transportation route, MOOVER, walking distance of restaurants and shops, 2 miles from Mt Snow and 0.6 miles from Mt Snow Golf Course. Close to hiking and biking trails and 6.8 miles from the charming town of Wilmington. Relax listening booke water running steps from the property, the perfect couple's getaway. 23 miles away from Brattleboro, 27 miles from Bennington and 33 miles to Manchester.

Jul 18 – 25

Cottage in North Bennington

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.

Home in Whitingham

Beaver's Bend Lakefront Retreat &~16 Mi to Slopes!

Tucked away in the bends of Whitingham, you’ll find our family’s home - "2nd Fiddle", where our Irish touch is sure to make you feel at home & our NYC energy will keep you entertained. Our home is stocked with paddle boards, canoes, games, Smart TVs, a fire pit, grill & more. To enjoy all Vermont has to offer, we are across the road from Harriman Lake & only 30 minutes from Mt Snow, with the towns of Wilmington & Dover peppered along the way. Come make memories to last a lifetime!

Oct 7 – 14