Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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Guest favourite
A tiny cabin with a unique Japanese-inspired design is nestled among tall trees, accompanied by a gravel pathway and a small fire pit. The cabin's natural wood exterior blends with the forest surroundings, creating a serene atmosphere beside a flowing brook.
Cabin in Downsville
4.88 out of 5 average rating, 318 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.

Superhost
A comfortable living area features a dark leather sofa and loveseat, accented with decorative pillows. A rectangular coffee table sits beside the sofa. A media console displaying a flat-screen TV is situated across from the seating, with large glass doors leading to the outside.
Townhouse in Binghamton
4.8 out of 5 average rating, 218 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.

Top guest favourite
The A-frame cabin is nestled among trees, featuring a wooden deck and wide glass doors that open to the interior. A private hot tub is positioned nearby, providing a relaxing outdoor space surrounded by nature.
Cabin in Damascus
5 out of 5 average rating, 214 reviews

Cozy A-Frame | Hot Tub, Fire Pit & Pet-Friendly

Escape to the Cedar Haven A-Frame in Damascus, PA – the perfect romantic hideaway just a short drive from NYC. Nestled in peaceful woods, this cozy 400-square-foot retreat offers all you need for a relaxing escape. Soak in the private hot tub, roast marshmallows by the fire pit, or unwind to music as you watch the forest through wide windows. Whether celebrating a special occasion or just needing time away, the tiny cabin invites you to unplug, reconnect, and make memories in nature’s embrace.

Top guest favourite
A two-story farmhouse features a white exterior with red shutters and a welcoming porch. Surrounding trees display varying autumn leaf colors, while the neatly landscaped front yard displays seasonal decorations amidst fallen leaves.
Farm stay in Susquehanna
4.97 out of 5 average rating, 111 reviews

Windcrest Country Home

Enjoy some time away in a renovated country farmhouse situated on 100 acres of farmland that raises Black Angus cattle. Located 3 miles outside of Susquehanna, PA we have ponds for fishing, swimming, and boating so bring your suits and fishing poles. We are surrounded by woods that have beautiful color in the fall. If you are a skier, Elk Mountain is only a short 25 minutes away. Any season is a relaxing time. After a peaceful day, end your night with a cookout and sitting around the fire pit.

Guest favourite
A newly constructed townhouse is featured, showcasing a blend of green siding and stone accents. The entrance is framed by a covered porch with white railings. A spacious driveway is visible, leading to a two-car garage. Lush landscaping complements the exterior.
Townhouse in Tunkhannock
4.84 out of 5 average rating, 101 reviews

Condominium Rental at StoneHedge Golf Course

Brand new townhouse on one of Northeastern Pennsylvania's Signature golf courses. Golf and romance packages available. Breakfast available upon request for an additional fee. Within steps of our seasonal on-site restaurant (April-October). This location is great for visiting family members, spending a couple of days on the course, and a romantic getaway with a loved one in the beautiful Endless Mountains. Easy access to Route 6 between historic downtown Tunkhannock and Clark Summit.

Top guest favourite
A gravel driveway leads to a secluded cabin nestled among tall pine trees. Sunlight filters through the branches, casting a warm glow on the landscape. The natural surroundings feature a blend of greenery and autumn foliage, creating a tranquil setting.
Cabin in Lisle
4.95 out of 5 average rating, 308 reviews

Private Cabin and Pond Property

Enjoy our secluded cabin, pond, and picnic area with many acres to roam. Rest comes easy with the privacy and peaceful woodlands that is the setting of our family's newly refurbished vacation space. Up to two Cots available upon request (must bring your own bedding.) Comfortable space for up to 4 guests. Our cozy cabin is the perfect chance to unplug from the busyness of life, equipped with WiFi but very sparse cell reception. WiFi calling feature can be used for important connections.

Top guest favourite
Cabin in Walton
4.94 out of 5 average rating, 222 reviews

The Mill House: An Enchanting Stream-Side Retreat

Nestled in the heart of the Catskills and just a 2.5-hour drive from NYC, escape to the perfect fall retreat where you can reconnect with nature and enjoy the serene beauty of the season. This historic gem underwent a recent restoration, 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.

Top guest favourite
Cabin in Binghamton
4.93 out of 5 average rating, 419 reviews

Cozy/Chic Cabin Binghamton NY

Retreat, isolated get-away but nearby town. This cozy cabin is rustic with some chic flair, decor & recent updates. Privately set on 2 wooded acres & near town. 2 stone fireplaces, indoor Jacuzzi tub, 2 1/2 BA, 3-4 BR & 7 person outdoor hot tub. Excellent WIFI, kitchen & dining. Picnic, grill & fire pit. Great fall foliage, near skiing, near hiking, boat launch. Fully outfitted, just bring yourself!! Willing to accommodate guests—ask!!

Top guest favourite
A serene cabin is situated next to a tranquil pond, reflecting the surrounding greenery. The dock extends into the water, offering a peaceful outdoor space. The area features a well-maintained lawn with tall grasses, enhancing the natural setting.
Cabin in Callicoon
4.99 out of 5 average rating, 213 reviews

The Cabin at Pleasant Valley Farm

The cabin is located on a dirt road on our farm with a beautiful pond and an amazing view! This off-grid, cabin has two queen beds (100% cotton sheets), a mini-kitchen with a battery-ignition gas range, solar powered refrigerator, solar lighting, a wood stove, an outdoor shower, a fire pit, and an old-fashioned outhouse. An expansive porch and dock provide comfortable outdoor living. A seasonal favorite, the cabin is available May-Oct.

Top guest favourite
An aerial view showcases the Over Water Bungalow with a green metal roof, surrounded by serene waters and lush greenery. The cabin features a wrap-around deck, enhancing access to nature, while the peaceful setting invites relaxation.
Cabin in Otego
4.99 out of 5 average rating, 160 reviews

Catskills Over Water Bungalow on Lake Albanese!

Catskills Cabin Rentals has designed and built one of the most unique places in the Catskills. Located on Lake Albanese is New York's first Over Water Bungalow featuring 2 bedrooms 1.5 bathrooms. The living room has a wood burning fireplace made with handcrafted stone. In front of the fireplace the home has a glass floor to see fish, turtles, frogs, and more! The home is located on 200 acres with only 4 other log cabins.

Guest favourite
A wooden sauna structure is positioned on a deck overlooking the calm river. Tall trees provide shade, while a mountain can be seen in the distance. The deck features a handrail, and the serene water reflects the blue sky and scattered clouds.
Home in Kirkwood
4.92 out of 5 average rating, 197 reviews

Susquehanna River House (Pet Friendly)

Welcome to the Susquehanna River House — a peaceful, 3-bedroom retreat on the Susquehanna River in Kirkwood, NY. Wake up to river views, sip coffee on the deck, and spend your day kayaking, fishing, or enjoying the sauna. Whether you're visiting for adventure or rest, this cozy escape offers the perfect mix of comfort, nature, and small-town charm — with Downtown Binghamton just 15 minutes away. Pets are welcome

Top guest favourite
A doormat featuring the words 'WELCOME TRAVELERS' in bold, black lettering. The mat is made of natural fibers with a textured surface, positioned on a wooden floor that showcases the warm tones of the flooring.
Home in Binghamton
4.91 out of 5 average rating, 415 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.

Popular amenities for Windsor holiday rentals

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