
Waterfront holiday rentals in Windham County
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in Windham County
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham County waterfront rentals
Waterfront apartment accommodation

Brookside Hideaway Retreat
Charming and cozy place with the river right in the terrace area. Magical! The place had everything needed for a comfortable stay. The kitchen well packed! Super clean and organized. 5mins drive to Mt Snow.

**Happy Hour! Gorgeous & Modern Downtown Retreat**
This place was absolutely awesome!! There’s a lake right down the street, we got in some good fishing over there😁 there’s also a dispensary and liquor store downstairs. Hands down the coolest dispensary I’ve ever been in. Also, love the golden retriever in the liquor store!! The flea market was right down the street as well as a small pink colored coffee shack. They had the best iced lattes and they use espresso cubes for ice! Can’t wait to go back!

A Beautiful Secret Den - with a private hot tub!
Beautiful location, great host! We loved the hot tub and the proximity to Magic Mountain. We will definitely be back!

Private 1st Floor Apartment/ Secluded Paradise
My stay at paradise Island was great and exactly what I needed for a couple weeks while I was working on a project ,I was able to relax ,rest, and enjoy a nice peaceful area and set my mind at ease ,met such wonderful hosts and very welcoming ,I appreciate the hospitality and what a beautiful place thank you again .

West Wing at Mantana Meadows on the West River
Perfect spot for a weekend getaway to Stratton. Everything was pristine when we arrived late in the evening. To our delight in the morning, we awoke to a view of the rushing river behind the house. Plenty of room for our party of four, and there was a good deal of entertainment from hundreds of DVDs and YouTube TV. Larry the host was right next door if we needed him. Highly recommend!

Globetrotter Retreat - Minutes to the Mountain
We had a great 4 day stay at Nina’s place. The apt is exactly as pictured and described on Airbnb. The space was a nice size, the furniture comfortable with the bed on the softer side, really good Water pressure in the shower, good amount of kitchen ware To create breakfast and lunches and light dinners. We loved the proximity to town and yet how quiet the place was, and there is a river directly in back. Nina was very prompt in responding to questions and gave us great recommendations for hikes in the area. There is a great bookstore and a number of really wonderful gift stores with Vermont artist’s works a block from the apt. And about a mile down the road starfire bakery with truly amazing baked goods. Make it a priority to Go there and try lots of things! We really loved our stay at Nina’s place and hope we can return in the fall or winter.
Waterfront house rentals

Spacious Brattleboro home on river, walk to town
It was perfect for my overflow guests attending a weekend family reunion!

Pinecone Pond
We had the most lovely stay at Pincone Pond. The house is absolutely spotless and well stocked with everything you need in the kitchen, shampoo and condition in the bathrooms and throw blankets for the cool evenings. The house is so homey and comfortable and the grounds are stunning. Beautiful yard and pond which were well cared for. Catherine has thought of everything including chairs for sitting by the pond or fire pit. Just a lovely, peaceful spot.

Frosted Willows
The place had great scenery and was comfortable. Weather was horrible throughout the weekend but we managed to have a great time in the home anyway. Chelsea was very responsive and helpful.

Magical Retreat Cottage - Waterfalls Everywhere
Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER
Wonderful place with great family room with fireplace especially when your weather doesn’t cooperate. The house is well kept and the instructions for everything were placed all around where needed. Fenced yard was great for the dog. The bed in the master is super comfortable with great linens. Loved the house-would live in it in a heart beat. Plenty of games, air hockey table, darts and another game table…grill, firewood- even poop scoops for the dog! Well done!

The Grafton Chateau
The Grafton house was perfect for our multi-family with the big space, bedrooms, and bathrooms. We loved the living room area where we could all sit together for family games. The property and house are beautiful and the perfect Vermont vibes. As a skiing family, we liked the location between our favorite ski resorts. Raphael was a wonderful host in providing instructions before our arrival and helpful advice. We really enjoyed our stay at the Gafton house.

Cozy Riverfront Home in beautiful Jamaica
Great place. Very isolated and a beautiful location but still has all the creature comforts. The deck, view, and space are amazing. Fast WiFi, 2 bathrooms, and a dishwasher with garbage disposal are really cool in a rustic location like this. The wood fires hot tub was obviously the star of the show. Clear instructions and good communication for everything. The gas grill and gas fire pit were nice. Every thing was comfortable and great. Stress free. Hope to stay here again, thanks for everything.

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts
What an amazing experience! Our kids loved every second of it. Our hosts were amazing, responsive, and inviting. The home was beautiful and the scenery was spectacular. I highly recommend staying here. It was a great life experience! Thank you!
Destinations to explore
- Rentals with a kayak Windham County
- Rentals with a hot tub Windham County
- Townhouse rentals Windham County
- Rentals with an EV charger Windham County
- Family-friendly rentals Windham County
- Rentals with a washing machine and dryer Windham County
- Fitness-friendly rentals Windham County
- Rentals with outdoor seating Windham County
- Rentals with beach access Windham County
- Beachfront rentals Windham County
- Pet-friendly rentals Windham County
- Bed and breakfasts Windham County
- Apartment rentals Windham County
- Rentals with a sauna Windham County
- Rentals with a patio Windham County
- House rentals Windham County
- Chalet rentals Windham County
- Rentals with pools Windham County
- Kid-friendly rentals Windham County
- Rentals with lake access Windham County
- Farmstay rentals Windham County
- Rentals with an accessible height toilet Windham County
- Private suite rentals Windham County
- Condo rentals Windham County
- Rentals with a fire pit Windham County
- Cabin rentals Windham County
- Rentals with a fireplace Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with breakfast Windham County
- Tiny house rentals Windham County
- Waterfront rentals Vermont
- Waterfront rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club
- Brattleboro Ski Hill