Beachfront holiday rental in Windsor County

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Popular amenities for Windsor County beachfront rentals

Pet-friendly beachfront home rentals

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

Four Season River Retreat: Private beaches & more!

DanielRating, 5 stars2 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)
Yurt in S. Strafford
4.67 out of 5 average rating, 27 reviews

20' yurt at creek

HollyRating, 5 stars27 months ago
Wonderful!! Bonna's place is well-stocked and thoughtfully arranged, and she is the best. The area is also wonderful for hiking and outdoor fun. Highly recommend!
Cottage in Ludlow
4.79 out of 5 average rating, 29 reviews

3BR lakefront with dock, swim platform, & firepit

MonikaRating, 5 stars1 month ago
vacasa was EXCELLENT. Extremely responsive and very accomadating. The pipes burst in our original booking and they put us in a different one without any hassle at all. Thank you so much for one of the best ski trips ever!
Superhost
Home in Plymouth
4.96 out of 5 average rating, 56 reviews

Renovated Family Lake~Ski House w/ gas fireplace

MaureenRating, 5 stars1 week 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.

Private beachfront home rentals

Guest favourite
Castle in Clarendon
4.98 out of 5 average rating, 465 reviews

Kingsley Grist Mill, Covered Bridge and Waterfall.

BrandanRating, 5 stars2 months ago
This is our yearly, must do trip. We have been going since 2020. We are already planning a summer trip for 2025! Ron and Linda are THE BEST! The Kingsley Grist Mill cannot be described in words or photos, it must be experienced! This time we finally got some decent snow which made it all the more magical. The local recommendations were perfect, we had plenty to do, and plenty to eat while out and about, but the breakfast provided is to die for! Absolutely divine! The concert provided by Ron is superb! And Sid is the most well behaved dog in the world! 10 out of 10, would recommend again and again.
Guest favourite
Cottage in Acworth
5 out of 5 average rating, 17 reviews

Classic lakeside cottage with gorgeous sunset view

KirstenRating, 5 stars7 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.
Yurt in S. Strafford
4.67 out of 5 average rating, 27 reviews

20' yurt at creek

HollyRating, 5 stars27 months ago
Wonderful!! Bonna's place is well-stocked and thoughtfully arranged, and she is the best. The area is also wonderful for hiking and outdoor fun. Highly recommend!
Cabin in Ludlow
4.75 out of 5 average rating, 236 reviews

Beautiful winter cabin near Jackson Gore

SeanRating, 5 stars2 weeks ago
Wife and I loved the home. What a beautiful spot on the river and down the block from Okemo , we would definitely rent the home again. Pete is on top of his response back if u reach out to him on your trip.
Cottage in Ludlow
4.79 out of 5 average rating, 29 reviews

3BR lakefront with dock, swim platform, & firepit

MonikaRating, 5 stars1 month ago
vacasa was EXCELLENT. Extremely responsive and very accomadating. The pipes burst in our original booking and they put us in a different one without any hassle at all. Thank you so much for one of the best ski trips ever!
Guest favourite
Cabin in Mount Holly
4.98 out of 5 average rating, 46 reviews

Lake House near Ludlow/Okemo and Killington

PaigeRating, 5 stars1 week 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, 11 reviews

Cheerful 4-br lakeside cottage- minutes to Okemo!

CharleneRating, 5 stars3 weeks ago
Christopher's place was absolutely wonderful - charming, immaculate, and tastefully renovated, with perfect amenities and lovely touches, like warm radiant floor heating, high quality dishware and cookware, and lovely views, too. We stayed for a ski weekend, and everything at the house was exceptional and comfortable, and felt like a very thoughtfully made home. Our family was super happy to be in the beautiful surroundings both inside and out. Such a treat to stay in such a beautiful space, with such a kind and easygoing host; indeed, we do hope to return again soon. Five stars! Highly recommend. Thanks so much Christopher!
Guest favourite
Home in Cavendish
4.93 out of 5 average rating, 43 reviews

Four Season River Retreat: Private beaches & more!

DanielRating, 5 stars2 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)

Destinations to explore