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 favorite

Cabin in Downsville

4.86 out of 5 average rating, 183 reviews

Tiny glamping cabin with mineral spring hot tub

This off grid, alternative powered site is located towards the front of a large twelve acre estate, alongside a flowing brook. Elevated over a natural spring that flows year round, the Japanese inspired aesthetics of this private, tiny cabin sits perched atop a deck among the wooded trees overlooking the waterway the mineral spring feeds, but not before filling the in-ground, cedar lined, two person, bubbling hot tub heated with a wood burning stove. One of two glamping sites on the 12 acres.

Guest favorite

Cottage in Oxford

4.93 out of 5 average rating, 100 reviews

✨Lakeside Reflections

🚣‍♂️ Lakeside Reflections is a year-round lakeside cottage in the quiet upstate NY countryside with pristine views of Lake Gerry. 🌻 Come enjoy a peaceful nook of historic Oxford complete with gardens, decks, docks, boats, and modern amenities. ♨️ Grill out on the lakefront deck, or fish directly off the deck! 🛶 Jump in the lake, or take a kayak, paddle boat, or walk around the lake. 🔥 Have a campfire (BYO wood) 🎟️ Enjoy one of the many local attractions (see our Airbnb guidebook for ideas)

Superhost

Townhouse in Binghamton

4.78 out of 5 average rating, 146 reviews

Lovely Custom Home

This is a great location to get to know the Greater Binghamton area - minutes from Binghamton University, SUNY Broome, downtown, Chenango Valley State Park. Visit with or entertain your whole family in a comfortable, safe area. Gas fireplace, beautiful two person jacuzzi tub, newly renovated kitchen. Great to stay while you tour the colleges, visit on parent weekend, enjoy the Southern Tier at large, or just have a stopping point on a longer journey. Easily get on and off from 81, 88, and 17.

Guest favorite

Chalet in Willet

4.96 out of 5 average rating, 140 reviews

Lakefront Home; private getaway, campfire & hikes!

Welcome to the Sunset Chalet - your serene, lakeside getaway! Gorgeous lakefront with lake access, over an acre of private land, and trails to explore! A private swimming pond & fire pits. Free use of 2 kayaks- 2 adult life jackets; and a canoe (Summer time). Rejuvenate with amazing views and hikes. We are conveniently located near Greek Peak Resort Ski Area, and Labrador Mountain. Not far from wine trails, Ithaca, and great hiking. Lots of open space. Relax, and savor the tranquility!

Guest favorite

Cabin in Walton

4.95 out of 5 average rating, 110 reviews

The Mill House: An Enchanting, Stream-Side Retreat

Escape and reconnect with nature at The Mill House, one of the most charming and beloved homes in the Catskills; just a 2.5-hour drive from NYC. Built in the early 1800s, this historic 1 bed/1 bath gem underwent a meticulous restoration in 2021, marrying its saw mill heritage with contemporary luxuries, including a Nest thermostat, smart speakers, keyless entry, and fast wifi. Original exposed post and beam construction and Scandinavian-inspired design make for a unique and cozy atmosphere.

Guest favorite

Chalet in Susquehanna

5 out of 5 average rating, 101 reviews

DEER RUN LODGE

Tucked away in the beautiful mountains of NE PA. Access to PA State Game land #299. 3 ski resorts within an hour drive. O&W snowmobile trail within a short drive. Fly-fishing on the West Branch of the Delaware River within 4 miles. Covered Deck, Gas Grill, Fire pit for cozy campfires. 20 minutes from 2 quaint towns offering restaurants, theaters, grocery stores. The weekend getaway place to read a book, hunt, fish, bird watch. NO PETS ALLOWED except for well trained service or hunting dogs.

Superhost

Cabin in Roscoe

4.86 out of 5 average rating, 483 reviews

Postcard Cabins Western Catskills - New York

An easy drive from the city, Postcard Cabins, formerly Getaway, is the ultimate way to experience the great outdoors. Nestled across acres of private woodlands, our tiny cabins have everything you need (AC/Heat, en-suite bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you disconnect from the everyday. As part of your stay, you'll receive a complimentary allocation of provisions, like s’mores, coffee and more.*

Guest favorite

Home in Binghamton

4.94 out of 5 average rating, 370 reviews

Quiet Private Apartment Park Setting West Side

This is an older home with one apartment on the first floor and a vacant apartment upstairs. Guests have the entire property to themselves. Free off-street parking. There is a small park across the street and a larger city park one block away w/carousel, pool, tennis courts, ice rink (all seasonal), amazing playground and walking paths. Three hospitals are within a 10 minute drive. Close to BU/SUNY. A nice variety of restaurants, bars, shops, antiques in the area. Check out the guidebook!

Guest favorite

Guest suite in Montrose

4.97 out of 5 average rating, 229 reviews

Hoots Inn, (formerly Noonan's Getaway)

If you are looking to escape to the woods and a lake this is your place. We are 25 minutes from Binghamton, NY and 35 minutes to Elk Mountain PA. Our place is comfortable and is your home for the time you are here. Complete house with lake access from the yard, kayaks, canoe, paddle boats, row boat and more. There is a pavilion, firepit and BBQ grill at your disposal. Peace and quiet with no motors allowed on the lake. NO PARTIES OR EVENTS ALLOWED DUE TO COVID CONCERNS.

Guest favorite

Home in Warren Center

4.99 out of 5 average rating, 180 reviews

Country Tucked Inn, with pond Sauna woods hunting.

Tucked Inn is a totally remodeled house in a quiet country setting. The pond offers swimming, a dock, pedal boat and fishing. The sunroom has a sauna for 2. The owners are next door and have a 500 acre family farm with beef cattle and a maple syrup operation. Sit on the front porch or grill on the back porch and enjoy the propane fire ring. Kids can run and play. Hunting available a mile away on a State Game Lands 219. Enjoy hiking in the large woods just out your back door.

Guest favorite

Home in Newark Valley

4.96 out of 5 average rating, 277 reviews

Private Scenic Retreat

The entire place is yours to enjoy! Our guest house is located on a dead-end road five minutes from the town of Newark Valley and only 30 minutes from Binghamton, Cortland, and Ithaca Included is a kitchen with open common area, two bedrooms, full bath and washer/dryer within living area. A farm setting is viewable from the common area and attached deck. There is a 2 acre pond and miles of scenic trails spread over 250+ acres, with sights as far as Pennsylvania!

Guest favorite

Home in Binghamton

4.92 out of 5 average rating, 354 reviews

The Milk House

Adorable little place to call your home away from home. Living room, kitchen with appliances, dishes, silverware, etc bathroom with accessories and king size bed. 2 big screen TV's with cable and WiFi. Dog and cat friendly with a fenced in yard and a dog run. Close by to Dunkin Donuts, restaurants, and grocery stores. Park is 2 minutes away if you want to get out and go for a stroll.