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Holiday rentals in Windsor

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Windsor

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

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Top guest favourite
A charming cottage is framed by vibrant pink rhododendron blooms, creating a striking entrance. A pathway of circular stepping stones leads from the grassy area to the front door, surrounded by lush greenery.
Tiny home in Oxford
4.96 out of 5 average rating, 385 reviews

⭐Wildflower Country Cottage

🏡 Cozy cottage in the countryside. Gardens galore to explore! 🏘 Less than 5 minutes from town 🎟 Many local attractions including: 🦒 Animal Adventure 🏎 Northeast Classic Car Museum 🥾 State Parks, and hiking trails 🚶‍♂️Enjoy an afternoon in the gazebo or take a stroll around any of the many garden paths. 📕 See our guidebook for our favorite local attractions and eateries. ℹ️ Please check out our other listing: Lakeside Reflections https://airbnb.com/h/lakesidereflections

Superhost
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
4.87 out of 5 average rating, 341 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.

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
4.98 out of 5 average rating, 261 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.

Guest favourite
An A-frame cabin is set amidst lush trees, featuring a spacious deck with a railing and steps leading to the exterior. Large windows reflect natural light, and the rustic wood facade is complemented by greenery surrounding the property.
Cabin in Susquehanna
4.98 out of 5 average rating, 160 reviews

Quill Creek Aframe

Welcome to our charming A-frame retreat near Elk! At 101 Longacre Rd, Susquehanna, PA! This cozy cabin features 2 bedrooms, 1 bathroom, a spacious deck, back patio, and a fire pit. Perfect for couples, families, or friends, our cabin offers a serene escape with modern comforts. Enjoy the stunning surroundings, unwind by the fire, or explore the beauty of Susquehanna. Ideal for those seeking tranquility and adventure. Book your stay today and create lasting memories at our lovely A-frame cabin!

Top guest favourite
A cozy living room features wooden beams and warm wood flooring. A comfortable dark sofa is complemented by a coffee table and a lamp. Artwork adorns the walls, while large windows allow natural light to fill the space, creating a serene atmosphere.
Home in Susquehanna
5 out of 5 average rating, 124 reviews

Olivia House

Olivia House is located in the quaint village of Steven's Point Pa. There is a large kitchen, dining & living room area and the original farm house features the family room which has been re-modeled but still retains the rustic farmhouse charm. The master bedroom has an attached bathroom with a large shower. The second bedroom is near another bathroom with a tub. There are 5 twin beds upstairs with an ajoining loft. A half bath is located in the laundry room. A BBQ grill inhabits the deck.

Top guest favourite
The exterior of the lake house is shown, featuring a gray facade with large windows and a welcoming front porch. Two black chairs are positioned on the porch, overlooking the serene lake and surrounding greenery, with a view of a paddleboat and other outdoor activities in the distance.
Cabin in Windsor
4.92 out of 5 average rating, 38 reviews

Halekulani is Beaver Lake

Enjoy this newly renovated Hawaiian style lake house at Beaver Lake with great views and charm of a cabin in the woods. This 2-bedroom property sleeps 6, has internet and WiFi with 2 Roku TVs, A/C, full kitchen, full bath, 3 eating areas, paddleboat, kayaks, and fire pit on a great fishing lake. Whether you are looking for a peaceful place to get away, a time to mix work with play, or just a change in scenery, the Halekulani is sure to meet your needs. Dogs are allowed for extra fee.

Guest favourite
A rustic cabin with a red metal roof is situated near a tranquil pond surrounded by green foliage. A large wooden deck extends from the front, offering views of the natural landscape. Stone steps lead from the pond's edge to the cabin, enhancing the serene atmosphere.
Cabin in Vestal
4.85 out of 5 average rating, 312 reviews

324 Knight Road, Vestal, NY

This cabin is a rustic getaway with all the comforts of home. Nestled in the woods, the cabin has an abundance of hiking trails with a covered bridge, and small farm that guests are welcome to visit. From APPROXIMATELY December 1 - March 1, the property is home to a full size sheet of ice. The rink and farm are featured in the 2022 Bauer Hockey holiday catalog. Be sure to bring your skates! A travelling massage therapist may be available for private bookings with a few days notice.

Guest favourite
A serene river view is framed by lush trees, with a grassy area leading to the water's edge. A gravel driveway provides access to the property, while power lines are visible against the sky. The scene conveys a peaceful outdoor setting suitable for relaxation.
Home in Windsor
4.81 out of 5 average rating, 70 reviews

Waterfront Vacation Rental

The property is a hidden gem, a private, relaxing, peaceful, cozy, quiet, fun getaway with a country setting, and access to the river for Kayaking, fishing, tubing & swimming. Grilling/Cookouts, & fire pits. Centrally located to Cole Park & State Park. Biking, hiking. Animal adventure, zoo, drive-in movies, restaurants, golfing, Chucksters family fun, skate estate, midway lanes, and fun zone, Our area is known for, wineries @ the 5 Great Lakes, spiedies sandwiches, maple syrups.

Top guest favourite
Home in Deposit
5 out of 5 average rating, 120 reviews

Couples Escape-Sauna-Cold Plunge-HotTub-eBikes

Enjoy a serene escape at the Scandi Farmhouse! Relax in the Finnish sauna, take a plunge in an antique cold tub. Snuggle by the bedroom gas fireplace. Melt away stress in the Hot Tub. Cruise a country road on an eBike. Enjoy a roaring campfire in the Solo Stove. Paddle on a nearby lake. Unwind to the sound of the tumbling brook and enjoy the wildlife. Spin vintage vinyl on the turntable, or strum an Ovation guitar. Enjoy a well equipped kitchen with a Sous Vide & quality cookware.

Guest favourite
Home in Harpursville
4.92 out of 5 average rating, 63 reviews

Hillside Haven w/ Great Views-King Bed-Pool Table

Relax with the whole family at this peaceful place to stay. This tasteful gem is newly remodeled top to bottom, and is perched on a hillside overlooking the beautiful Susquehanna River valley. Challenge your friends to a game of pool in the game room, or relax on the huge deck and enjoy the view. (up to 15 miles on a clear day!) This property is located a quick 25 minutes from Binghamton, only 6 minutes from Animal Adventure Park and 9 minutes from Nathaniel Cole Park.

Guest favourite
A rustic cabin is nestled among lush trees, featuring a metal roof and warm, inviting windows. Soft lighting from the windows enhances the natural surroundings, while a stone walkway leads to the entrance, blending harmoniously with the forest landscape.
Place to stay in Downsville
4.88 out of 5 average rating, 229 reviews

Half Moon: Fairytale Catskills Retreat

Enjoy nature in style at this fairytale in the forest. This idyllic escape combines whimsical structures, curated gathering spaces and a private wooded hillside surrounded by hiking trails and quaint towns. Disclaimer: This is a rustic cabin. Heating is from a wood-burning stove, there is no AC. The bath house is a separate structure from the cabin, up a hillside with stone steps. Cooking is via charcoal grills, small outdoor kitchenette or fire.

Guest favourite
A spacious living area is furnished with a prominent red sectional sofa surrounding a circular coffee table. Natural light filters through the windows, illuminating the neutral-colored walls and flooring. A decorative wall art piece enhances the ambiance, while a ceiling fan adds comfort.
Flat in Ouaquaga
4.94 out of 5 average rating, 32 reviews

Rural Retreat

Relax on 4 acres of nature in a rural setting of Upstate New York. The backyard butt's up to the Susquehanna River, hop on in! Walk down the street to see the neighbors cows and horses or to the boat ramp access. Community members occasionally do sunset yoga on the walking Ouaquaga bridge (2 min walk) from the property. There's also a park close by and the zoo Animal Adventure within 3 miles. At night cozy up in the open concept apartment.

Popular amenities for Windsor holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Broome County
  5. Windsor