Beachfront vacation rentals in Windsor County

Find and book unique beachfront homes on Airbnb

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Popular amenities for Windsor County beachfront rentals

Pet-friendly beachfront home rentals

Guest favorite
Home in Cavendish
4.93 out of 5 average rating, 43 reviews

Four Season River Retreat: Private beaches & more!

DanielRating, 5 stars5 months ago
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)
Cottage in Ludlow
4.79 out of 5 average rating, 33 reviews

3BR lakefront with dock, swim platform, & firepit

EricRating, 5 stars2 months ago
We had an amazing stay at this beautiful house for a weekend ski getaway. The house is located on a gorgeous lake just minutes from Okemo, making it a perfect stay for Skiing. The views of the lake are spectacular with direct lake front access. We had a very comfortable stay and enjoyed the hot tub after skiing as well as sitting in the living room by the gas fire place. This is by far one of the nicest AirBnBs that we have booked near Okemo and we look forward to staying at the house again in the summer and winter.
Superhost
Home in Plymouth
4.96 out of 5 average rating, 56 reviews

Renovated Family Lake~Ski House w/ gas fireplace

MaureenRating, 5 stars3 months ago
Place was beautiful and very well appointed. Comfortable beds and plenty of room for a weekend of skiing with 7 adults We had a small issue with parking due to a large snowfall. We needed all four parking spots but the driveway wasn’t completely cleared. Melanie was very responsive and we were able to park 4 cars. Just something to be aware of if you’re coming in the winter.
Home in Stockbridge
New place to stay

Riverfront Retreat in Stockbridge

Private beachfront home rentals

Top guest favorite
Castle in Clarendon
4.98 out of 5 average rating, 468 reviews

Kingsley Grist Mill, w/ Private Beach & Waterfall

CarolineRating, 5 stars2 days ago
This was our second fabulous stay at the historic Kingsley Gristmill. What a uniquely wonderful place. Ron and Linda provided all of the creature comforts we could ask for, including scrumptious breakfasts. The sight and sound of Mill River (our two balconies overlook the River) were magnificent. The Mill is filled with historic treasures and art. We went on several beautiful hikes nearby, and visited Manchester, the Killington area and Woodstock, all easy day trips. We will definitely return. Five huge stars.
Guest favorite
Cottage in Acworth
5 out of 5 average rating, 17 reviews

Classic lakeside cottage with gorgeous sunset view

KirstenRating, 5 stars11 months ago
We just got back from an amazing few days at Breezy Pines. Mary was always quick to respond to any questions I had. The cottage was well equipped from kitchen supplies to comfortable linens and towel, Wi-fi, as well as wood for the fire pit. We enjoyed lazy days lounging in the sun and swimming. Meals were enjoyed on the screen porch overlooking the lake. Amazing sunset views. We enjoyed every minute of our stay.
Cottage in Ludlow
4.79 out of 5 average rating, 33 reviews

3BR lakefront with dock, swim platform, & firepit

EricRating, 5 stars2 months ago
We had an amazing stay at this beautiful house for a weekend ski getaway. The house is located on a gorgeous lake just minutes from Okemo, making it a perfect stay for Skiing. The views of the lake are spectacular with direct lake front access. We had a very comfortable stay and enjoyed the hot tub after skiing as well as sitting in the living room by the gas fire place. This is by far one of the nicest AirBnBs that we have booked near Okemo and we look forward to staying at the house again in the summer and winter.
Cabin in Ludlow
4.73 out of 5 average rating, 247 reviews

Beautiful Lake Cabin near Jackson Gore 4 Families

DaphneRating, 5 stars3 weeks ago
My husband and I found this an excellent value for a weekend getaway in Vermont. We enjoyed hiking and shopping nearby, and paddling on this little lake (it's really a long, narrow pond). The kitchen, bathroom, and floors of the cabin are newly renovated. The kitchen has everything you could possibly need without being cluttered. The water side location is pastoral and we saw beaver, geese, and goslings all from the picture window.
Guest favorite
Cabin in Mount Holly
4.98 out of 5 average rating, 46 reviews

Lake House near Ludlow/Okemo and Killington

PaigeRating, 5 stars3 months ago
We had a lovely stay at Ambers place. Her home is extremely cozy and homey—the perfect vibe for a lake / ski weekend. It’s very spacious (the photos don’t do it justice), had a well stocked kitchen, and a pretty lake view. About 10 mins from Okemo and 30 mins from Killington. Would definitely recommend!
Cottage in Ludlow
5 out of 5 average rating, 12 reviews

Cheerful 4-br lakeside cottage- minutes to Okemo!

TimothyRating, 5 stars3 months ago
Beautiful, well equipped home on a lake. The house was very cozy with beautiful views of the lake and Okemo mountain. Bedrooms were perfectly configured for our family of 5, with plenty of bathrooms and seating areas throughout. House had great heating options (radiant heat, heat pumps and gas fireplace) to stay comfortable during a very, very cold week of skiing. We saw a bald eagle as well! Very easy to access Jackson Gore base area (5 minutes) and only a few more to the main base area. 10 minutes to town. Couple great restaurants nearby. Host was very responsive and accommodating. We arrived during a massive snow storm and Chris was very helpful addressing issues with plowing and shoveling of driveway/walkway. One thing to note is that the house is located on a gravel/dirt road. You need a 4WD vehicle with proper tires to access this area safely during bad weather. Would stay again!
Guest favorite
Home in Cavendish
4.93 out of 5 average rating, 43 reviews

Four Season River Retreat: Private beaches & more!

DanielRating, 5 stars5 months ago
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)
Home in Ludlow
4.87 out of 5 average rating, 93 reviews

Tranquil Ludlow Waterfront Retreat

DaneenRating, 5 stars2 months ago
Brian's house was a great home base for our week-long ski vacation. Check-in was easy and we fit comfortably with 4 adults and two children under 5. The kitchen was well-equipped (we cooked at the house a lot). The mattresses and pillows were perfect for us (on the firmer side). Communication with Brian was fantastic. We had one home maintenance issue that came up during the week and Brian was very quick to engage the right people who got it resolved for us. The location was perfect. We enjoyed looking at the river through the living room windows and even watched as a beaver walked around down there. The house was a short 10 minute drive to Okemo and Ludlow (which has a good grocery store). The Green Mountain Sugar House was on the way home from the ski hill, where we stopped to get maple frosties for the kids. There was also a nice hike 10 minutes away at Buttermilk Falls, where we saw beautiful ice formations around the falls. We would love to come back again in the summer!

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