Beachfront holiday rental 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 favourite
Home in Cavendish
4.93 out of 5 average rating, 43 reviews

Four Season River Retreat: Private beaches & more!

DanielRating, 5 stars3 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 stars28 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
4.81 out of 5 average rating, 31 reviews

3BR lakefront with dock, swim platform, & firepit

EricRating, 5 stars3 days 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 stars1 month 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

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

Kingsley Grist Mill, w/ Private Beach & Waterfall

BrandanRating, 5 stars3 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 stars8 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 stars28 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
4.74 out of 5 average rating, 242 reviews

Beautiful winter cabin near Jackson Gore

JacenRating, 5 stars3 weeks ago
Super convenient location. Easy access. Very clean and spacious , definitely recommend.
Cottage in Ludlow
4.81 out of 5 average rating, 31 reviews

3BR lakefront with dock, swim platform, & firepit

EricRating, 5 stars3 days 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.
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 month 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 stars1 month 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 favourite
Home in Cavendish
4.93 out of 5 average rating, 43 reviews

Four Season River Retreat: Private beaches & more!

DanielRating, 5 stars3 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)

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