
Waterfront vacation rentals in Windsor County
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Top-rated waterfront accommodations in Windsor County
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Vacation rentals for every style
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Popular amenities for Windsor County waterfront rentals
Waterfront apartment rentals

Private Riverside Studio* Upper Valley*Vermont
Nice place, small and quaint. I don’t think it’s suitable for a long term stay, but good for a quick weekend and has the necessities needed for a short stay.

Spacious, Sunny, Second Story 2 Bedroom Apartment
Overall A great place. Would def book it again. -Very spacious. We are a fam of 3 and more than enough for us. Easily could fit a fam Of 5. -Clean.

Connecticut River Odyssey
Liz is a very kind and accommodating hostess. We would definitely go back.

Dog heavenly! Private, beautiful and relaxing.
The place had everything I was looking for. Very peaceful, private and safe 👌🏽 Loved de sound of the river in the backyard and to be able to sit by it and enjoy the sense of peace that it gives. Surrounded by nature, the place is just perfect for that well-needed getaway to unwind and relax 👌🏽 That Superhost title is well-earned! Liz is such a wonderful host 👏🏽 She is super responsive, very attentive, wonderfully helpful and kind 🧡 She helped me make the most of my stay 🧡 Poop Stick is such a lovely dog 🥰 I will definitely be staying again in the future. Highly recommended place ⭐️⭐️⭐️⭐️⭐️

49 River Street
Our stay at Michael’s was perfect for what we needed. Our son lives nearby so this rental provides a convenient place to stay when we visit. Michael was very accommodating. We had mentioned an extra person might be with us and we were surprised to find an air mattress and pillows waiting for us. We were pleasantly surprised that we didn’t need to walk to the coffee shop in the morning. A Keurig with pods and a delightful selection of tea, hot cocoa and creamers saved us a trip. We will definitely be returning.

Rustic 64 Acre Woodland Haven on a Beautiful River
We really enjoyed our time at Kevin’s place. The listing was as described and Kevin was really proactive and helpful when we had questions. There was going to be a big storm that would have snowed us in the day we were supposed to check out so we decided to leave a day early. Kevin offered to refund our final day which we really appreciated

Vermont Studio Getaway in historic Woodstock VT
Great little place for a couple or a small family (at most 2 toddlers). Lots of stuff near by to everyone to do. The bedroom and the living room are a common room which was great for us because we all fell asleep at the same time after a fun and busy day!

Ski Getaway in the heart of Vermont
Collen is very nice and thoughtful. The space is mostly as described, however you can't go on the back porch where the nice view would be. Also, it is directly off the road which is a pretty busy highway, and for some, like us, is not ideal or safe feeling.
Waterfront house rentals

Twin Mountain River House
The house was beautiful and in a perfect location. Everything was clean and well cared for. The owner was very responsive and detailed—we didn’t need to message them at all during our stay! Would recommend to everyone.

Lakeview | Family-friendly | Stargaze | Relax
This lake house lives up to all wonderful reviews it has been given. So comfortable, open , and beautiful scenery. My husband, myself and our dog spent several days enjoying the peaceful surroundings. We saw loons,Canadian geese, mallards, kingfisher, and even an eagle that swooped in for a fish . The house itself has all the comforts of home you could need. We loved the coffee mugs so much that we bought some for home! Also a Nespresso machine may be in our future. Thank you to Danielle and family for creating such a welcoming and serene home.

Cornish-Windsor Bridge Retreat with Amazing Views
We had a lovely stay at Jonathan's place at a pretty much perfect time of year. The views were incredible! The home had a ton of character, and somehow managed to be cozy despite being huge. The view from the shower/bath did not get old! We would definitely recommend to friends and family looking for a getaway.

Cozy Crescent Cottage
Everything about our stay was amazing! The views were beautiful! The hosts were quick to respond whenever I reached out. They provided anything and everything you could think of! We had so much fun hiking on the trail to the small waterfall just minutes from the cottage, kayaking, and playing games they had. It was so nice to stay at a place that made us feel at home.

BEST OF LAKE FRONT LIVING, HOT TUB & FIREPIT !!
This place was perfect inside and out. It looked exactly like the photos. It was unique and inviting. Nicholas was amazing with his communication, help, and we truly felt like he went the extra mile. The house was well stocked. The beds were very comfortable and the couches upstairs were a favorite place to relax and unwind. There was a nice place for a fire outside and plenty of wood. We would 100% recommend staying here!

Amherst 1: Lakefront Cabin!
This place is beautiful, meticulously organized and have everything you need! It’s great for a small family or group of friends that want to unwind on the lake. I’ll be back!

Four Season River Retreat: Private beaches & more!
We had a great stay. Everyone really loved the farmhouse feel. Check in was easy and Jarad was very responsive and accommodating. We would have loved to use the outdoor space and bar but it was just too cold this visit, we will be back to give that all a shot when the weather warms up. There was a great local grocer not to far away and the ski mountain was just a short drive. This was a great place to stay and it had the first indoor toilet in cavadish (at least according to the previous owner)

On Silver Lake & Close To Woodstock
Beautiful clean home situated right on the lake. Felt right at home. Diane was amazing in sending our group local recommendations, food, entertainment. She was so proactive and accommodated early check in time. Diane’s home was filled with amenities. From expansive living room with fire place to full kitchen filled with amenities, her home felt right at home. Can’t wait for our next visit
Waterfront condo rentals

2BR Riverfront 2nd-Floor | Balcony |
Great stay if you’re looking for something close to the mountain but still right in town! Walkable to everything on Main Street. The apt was as advertised and easy to access and had everything we needed to enjoy a ski weekend.

Spacious 4BR Lakefront | Deck | Pool
Nice house, very comfy

Golfer's Paradise
Great Place! You have everything that you need in the house and, you can’t be on a better location !
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- Stratton Mountain
- Okemo Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Pats Peak Ski Area
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Hooper Golf Course
- Bretwood Golf Course
- Dartmouth Skiway
- Veterans Memorial Recreation Area Ski Hill
- Baker Hill Golf Club
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Santa's Land USA
- Brattleboro Ski Hill
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