Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Cabin in Bovina Center

4.97 out of 5 average rating, 395 reviews

Delightful Cabin with Extras

SarahRating, 5 stars1 month ago

Had a lovely long weekend at Pamela & Alan's warm, cozy home. We made good use of the wood stove, grill, and hot tub and took advantage of the board game and DVD selections as well! We also enjoyed the local attractions such as the Putt Putt Van Winkle mini golf course, Brushland Eating House and Bovina Farm & Fermentory for delicious dinners, Wayside Cider, and even went for a little hike nearby. The house was clean and comfy and we felt right at home - thanks to Pamela and Alan for the wonderful stay!

Top guest favourite

Cottage in Beach Lake

4.99 out of 5 average rating, 116 reviews

Driftwood Cottage on Welcome Lake-peaceful retreat

ChristinaRating, 5 stars6 days ago

I cannot say enough about this home. If you’re looking for a peaceful getaway with beautiful views, this is the place for you. Hosts were extremely helpful & very quick to respond. We got lucky with beautiful weather and got to enjoy the lake but, stargazing in the jacuzzi at night was a perfect touch. We seriously loved every bit of this home and would love to return one day!! Thank you Bob & Julie!!

Superhost

Home in Lake Ariel

4.87 out of 5 average rating, 129 reviews

Lakeview Chalet - Pool & Lake/Beach - Kayaking

Luz AngelaRating, 5 stars4 months ago

Great deck and view of the lake - peaceful and relaxing. The house had all the amenities we needed - great grill, large sitting area and TV to hang out with family. The kids enjoyed playing in the downstairs area and roasting marshmallows out back.

Top guest favourite

Cottage in Livingston Manor

4.99 out of 5 average rating, 146 reviews

Cozy mountain top home - views, 5acres & a gym.

NikhilRating, 5 stars2 weeks ago

The cottage was lovely and very comfortable. Simon left us detailed instructions and we had no issues in finding it and settling in. As the weather took a turn for the worse, we spent most of a day cozy in the house. Our dogs were also very comfortable and loved the large backyard. The house decor is very tastefully done, and not only looks great but looks like special effort has been taken to make everything comfortable and easy to use. Thank you for sharing your home!!

Guest favourite

Home in Lake Ariel

4.82 out of 5 average rating, 78 reviews

20% discount! Holiday special! Poconos Best place!

CeydaRating, 5 stars2 months ago

Javid & Aysel are great hosts, super quick to respond and very helpful. They have a very lovely, homey home, and our group of 13 really enjoyed every level of it. We enjoyed the wood burning fireplace as the family gathered around it and by the kitchen/dining area. The house sits very close to walking trails, ski slopes, and it’s walking distance to beach and the community center which we would like to come back for in the summer!

Superhost

Home in Oneonta

4.89 out of 5 average rating, 28 reviews

1st Class Rentals-#1 Location for Baseball Parents

EricaRating, 5 stars8 months ago

Great location - easy to walk to the main strip that has restaurants. Short drive to gas, DD, bigger chain restaurants, grocery stores, etc. Small park few blocks away for the kids to play wiffle ball. Plenty of parking by the house. Easy drive to All-Star Village. House is equipped with everything you need. The house has beautiful stained glass windows and a lot of "old charm" to it. Lovely front porch to sit outside and enjoy coffee. But expect older appliances, flooring, cabinets, drawers, furniture, windows, bedding, etc. Everything was in working condition. House is spacious and easily accommodated us. We enjoyed our stay very much. Dave made it very easy, provided an early check in which was very helpful to get settled before the ASV parade. One of the families who has a younger son (who hopes he will also play at ASV in the future) already said she would book here again! Thanks Dave!

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Other great vacation rentals in Windsor

Superhost

Home in Laceyville

4.87 out of 5 average rating, 30 reviews

Heated Pool, Cozy 5BR Getaway-Games-Hikes-Wineries

LalaRating, 5 stars8 months ago

The place is clean, peaceful, lovely, quiet. My family had so much fun, especially the pool. Thank you very much.

Guest favourite

Cabin in Hawley

5 out of 5 average rating, 40 reviews

Beautiful Cabin Retreat Getaway in the Woods!

CharlesRating, 5 stars2 months ago

The place was gorgeous- exactly like the pictures. We celebrated my birthday this weekend. Our stay was cozy surrounded by nature. A great place to disconnect. The house was spotless and beautifully decorated. I would definitely stay here again.

Top guest favourite

Home in Barryville

5 out of 5 average rating, 14 reviews

Luxury Mountain Retreat with Panoramic Vista Views

RebeccaRating, 5 stars1 month ago

Mike’s cloud-cabin FAR exceeded our expectations. The view and stay was, by far, our best experience with Airbnb. This was more of a zen retreat over your average home rental. Every corner of the home was designed thoughtfully and with architectural purpose and intent. Truly a gem. Mike was also super accommodating, quick to respond, and extremely kind. The only thing I would change is the fact that we had to leave! I will definitely be booking again. Thank you, Mike!

Guest favourite

Home in Lakeville

4.93 out of 5 average rating, 124 reviews

The Great Escape

CristhianRating, 5 stars4 months ago

Great place. House is lovely, clean and peaceful.

Guest favourite

Home in Endicott

4.96 out of 5 average rating, 56 reviews

Nice 3-bedroom home in quiet community

HeatherRating, 5 stars2 weeks ago

It was everything we could have hoped for while we visited my son at college. We will definitely be back next time!

Superhost

Home in Monticello

4.9 out of 5 average rating, 39 reviews

Modernist Lakefront Sojourn

ShehryarRating, 5 stars3 weeks ago

This accommodation is a great choice to get away from the noise of the city. The house is decorated beautifully and there no lack of space. We especially enjoyed the lake side deck and all the extra amenities like pool tables, ping pong, Jacuzzi and such. There was even a kayak near the lake if you are interested. The host was also very proactive and responsive to our every need and provided great instructions for check in, check out and house rules.

Superhost

Home in Nineveh

4.79 out of 5 average rating, 61 reviews

Peace Of Heaven Ranch - Wildlife, Nature, Serenity

DonnaRating, 5 stars7 months ago

We loved the property. It was beautiful and private. We enjoyed the fire pit and had a campfire each night! We saw deer and wild turkeys on the property. The house was perfect for the 10 of us. The host was so helpful and responded to our questions quickly. Thank you for sharing your house with our family!

Guest favourite

Home in Monticello

4.87 out of 5 average rating, 15 reviews

Luxurious & Newly Renovated Catskills Lakehouse

ShelbyRating, 5 stars1 month ago

We had a weekend youth retreat and stayed at Alan’s spacious home. We had a great time together. the home was as described, the hosts were very friendly and accommodating, and everything was clean and in good condition. Would definitely recommend for a big group!

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Vacation rentals in Windsor

Top-rated vacation rentals in Windsor

Vacation rentals for every style

Popular amenities for Windsor vacation rentals

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