Waterfront vacation rentals in Windham County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Windham County

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

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Guest favorite

Home in Grafton

4.93 out of 5 average rating, 106 reviews

The Grafton Chateau

Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

Guest favorite

Home in Jamaica

4.94 out of 5 average rating, 167 reviews

Cozy Riverfront Home in beautiful Jamaica

. Surrounded by tall pines and mountains, with the tranquil sound of the West River outside, here you can escape into nature while still enjoying all the cozy comforts of home. Our newly renovated home has been transformed into a getaway spot for romance, friends or family. The deck, set on the waterfront, is a beautiful, serene space to dine or take a soak in our wood burning hot tub. Put on some records, make a meal and cuddle up in front of the fire after a long day of playing outdoors.

Superhost

Home in South Londonderry

4.84 out of 5 average rating, 128 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

This VERY NEW and VERY romantic treehouse is finished!!! The Honey Pond Treehouse is made especially for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…You will enjoy private hot tubbing, sauna time, relaxing, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes…biking & disc golf at Magic Mnt!

Guest favorite

Chalet in Jamaica

4.98 out of 5 average rating, 241 reviews

Vermont Chalet

Escape to our cozy A-frame on 3 private acres in Southern Vermont for a peaceful, secluded retreat. Relax to the soothing sounds of the river across the street while unwinding on the covered, screened-in porch. Enjoy a fully stocked kitchen, updated bathroom, strong WiFi, video games and books by a warm wood stove. Explore local towns, hike, or wander through our tranquil forest. With an EV charger, local artisan soaps, and warm woodstove, this is the perfect spot for a serene getaway.

Guest favorite

Cabin in Newfane

4.98 out of 5 average rating, 253 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

Come stay in our sparkling clean, renovated log cabin in the woods with beautiful views of river, mountains and stars. Located by the charming village of Williamsville, close to historic Newfane village, 12 miles from Mount Snow for skiing, and right on the refreshingly cool and clear Rock River. It's the perfect place for a romantic getaway, a family vacation or quality times with dear friends. Recent addition: outdoor hot tub with views of mountains, river and open sky above.

Guest favorite

Cottage in Newfane

4.97 out of 5 average rating, 115 reviews

Silk Purse Cottage on Baker Brook

The "Silk Purse" started life in the 60's as a 10x40 mobile home. Its placement next to Baker Brook offers a private view out of every window and easy vehicle access. The screened porch is a relaxing place to have coffee or cocktails. Extra windows add interior light in this shaded woodland setting, and a beautiful 12x14 addition with a skylight and a full wall of glass give an unobstructed, private view of the stream. 20 minutes to Brattleboro, 30 to Stratton, 25 to Mt. Snow.

Guest favorite

Rental unit in Brattleboro

4.98 out of 5 average rating, 119 reviews

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by. A half hour from skiing and 5 min away from snowmobile trails. A gorgeous view of the river and mountain across the street .

Guest favorite

Home in Londonderry

4.98 out of 5 average rating, 112 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, 463 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!!!

Guest favorite

Home in Brattleboro

4.95 out of 5 average rating, 115 reviews

Spacious Brattleboro home on river, walk to town

Look no further for the perfect retreat. This spacious area for AirBnB guests (approx 3,000 sq feet) consists of 4 bedrooms, 4 bathrooms (2 en-suite), a formal living room & dining room, a TV-room, and kitchen (eat-in) with family area opening onto a deck. Dramatic river & Wantastiquet Mountain views (foliage or greenery). Ten minute walk to Brattleboro Main Street.

Guest favorite

Guesthouse in Putney

4.97 out of 5 average rating, 264 reviews

Cozy cottage loft and retreat

Returning guests, please ask about our discount! Relax and recharge in our peaceful Vermont cottage. Enjoy this sweet getaway with hardwood floors, fast wifi, a fully equipped kitchen, a quiet sleeping loft with a queen size bed, gorgeous natural light, views of surrounding hills and pond, gardens, and your own private entrance and back deck next to the Putney Brook.

Guest favorite

Rental unit in Newfane

4.97 out of 5 average rating, 430 reviews

Rock River Retreat: VT Oasis Pet Friendly

Your private treetop guest suite and beach await at our 1790's colonial on the Rock River in the quiet village of South Newfane, VT. PLEASE READ THE ENTIRE DESCRIPTION BELOW RE: PET POLICIES & kitchenette details. We welcome your furry family members for a $10 fee per pet, per day.