Vacation rentals in Windsor

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Popular amenities for Windsor vacation rentals

Other great vacation rentals in Windsor

Guest favorite
An outdoor pool is surrounded by lounge chairs and red umbrellas. Lush green trees frame the space, creating a serene environment. A small poolside shed is visible, adding functionality to the area.
Condo in Killington
4.75 out of 5 average rating, 92 reviews

Still 89 Trails Open, Low, Low Rates

RyanRating, 5 stars1 month ago
Convenient to the slopes via the shuttle that picks up out front. Able to walk to a good restaurant, Still on the Mountain. Place is comfortable and has everything we needed for a weekend skiing.
Superhost
The entrance to the property is framed by a bright yellow exterior, featuring two sets of double doors labeled A and B. Potted plants are placed on either side of the doors, and a gentle pathway leads towards the entrance.
Apartment in Bristol
5 out of 5 average rating, 3 reviews

1 bedroom near Ragged Mountain & Newfound Lake

LianaRating, 5 stars6 months ago
Had a lovely longer-term stay here. The house is beautiful with classic old New England character but totally modern features inside. Walking distance to several walking trails and coffee shops and short drives to countless places for swimming, hiking, rock climbing, and walking. The hosts were extremely kind and accommodating. No complaints here, we had a wonderful stay!
Guest favorite
A billiards room features a vibrant red pool table at its center, surrounded by wooden flooring. Natural light floods in through large windows, highlighting the contemporary decor. An antler chandelier hangs above, while colorful glass items are displayed on a sleek, white shelf against the wall.
Home in Bellows falls
5 out of 5 average rating, 9 reviews

Amazing Views, Skiing Nearby and Amenities Galore!

GillianRating, 5 stars2 months ago
We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!
Guest favorite
A firepit surrounded by red adirondack chairs is placed on a snowy lawn, with a cozy fire burning in the center. The two-story retreat is visible in the background, featuring expansive windows and solar panels on the roof, all under a clear blue sky.
Home in Newport
4.9 out of 5 average rating, 88 reviews

Berry Mountain Lodge: Mountain Views by Lake & Ski

MelissaRating, 5 stars1 month ago
This house was great for a large group to visit Sunapee area. Cassandra was responsive and helpful. The house was clean, neat, very well stocked, and had plenty of space and things to do.
Guest favorite
Home in Gilford
4.88 out of 5 average rating, 201 reviews

Fun & Fabulous Getaway

Joshua MichaelRating, 5 stars2 months ago
My family booked this place because it was close to Gunstock. With plenty of room for the entire family and cozy living area, it had everything we needed. Mohammed was very attentive to any questions we had, and the place had everything we needed and more. The only recommendation I have is to clean more of the snow from the back deck. We had trouble accessing the grill.
Top guest favorite
The modern wooden exterior of the home features large windows that allow natural light to brighten the interior. A spacious deck extends from the second floor, surrounded by lush green grass and colorful autumn foliage.
Home in Plymouth
5 out of 5 average rating, 16 reviews

Luxury Modern Cabin near Okemo & Killington

TariQRating, 5 stars1 month ago
Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!
Superhost
A covered porch features several lounging chairs and a picnic table, providing an inviting space to relax. Lush greenery surrounds the area, with an expansive lawn visible in the distance under a clear blue sky.
Home in Meredith
4.85 out of 5 average rating, 20 reviews

Perfect Lakeview Family Getaway

BradyRating, 5 stars2 months ago
Devon's place worked really well for our Ski Trip. It is located very close to Gunstock mountain and the house was clean and new. Was a little smaller than expected from the photos but nonetheless we had a great time and a great stay. Didn't spend too much time in the space but the location is the best part as it is very close to Gunstock and other ammenities.
Superhost
The exterior of a contemporary A-frame house is set amidst a forest, featuring a new deck with outdoor space. A pathway made of stones leads to the entrance, while sunlight filters through the surrounding trees, casting soft light on the facade.
Home in Jamaica
4.75 out of 5 average rating, 57 reviews

Green Mountain A-Frame with HOT TUB near Stratton

AdrianRating, 5 stars1 month ago
Had an excellent time and the cabin is extremely convenient for any nearby skiing! The house was very well kept (plenty of firewood available, hot tub was clean and ready to go on check-in, grill was gassed up, etc.), and plenty of space for even a large group. Would definitely recommend.

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