Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

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Top Guest favourite
The image captures a serene lakeside view at sunset, with sunlight reflecting on calm waters. The cottage's exterior and a small dock are visible, framed by wildflowers and trees. The tranquil atmosphere presents an ideal setting for relaxation and enjoyment of nature.
Cottage in Oxford
4.92 out of 5 average rating, 145 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)

Top Guest favourite
A spacious living room features two comfortable gray sofas and a decorative coffee table, positioned around a large screen TV. Natural light filters in, enhancing the warm tones of the walls. A small side table with a lamp adds to the cozy ambiance.
Apartment in Greene
4.98 out of 5 average rating, 181 reviews

New Downtown Greene Apartment *no cleaning fee!*

This spacious one bedroom apartment overlooks peaceful downtown Greene. A quaint little village known for its unique shops and chic restaurants. This apartment gives you 1000+ sqft of a home away from home, equipped with all the amenities: washer/dryer, full kitchen, living room, bedroom, & off-street parking. This beautifully designed, modern apartment is perfect for the business traveler or family staying for recreational purposes. One bedroom with a pullout couch & air mattress, sleeps 6.

Top 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, 133 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!

Guest favourite
A bright living area features a comfortable leather seating arrangement, accented by teal cushions. A wooden coffee table sits in front of the seating. Large windows draped with sheer curtains allow natural light to fill the space, while a television is positioned on a low stand against the wall.
Townhouse in Binghamton
4.88 out of 5 average rating, 172 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, large two person tub, extra basement suite w/bed+bathroom. 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 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
4.84 out of 5 average rating, 291 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.

Top Guest favourite
Cabin in Walton
4.94 out of 5 average rating, 212 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
The riverfront cabin is set amidst tall trees, with warm exterior lighting illuminating its entrance. A wooden deck leads to the front door, while the surrounding landscape features serene greenery and gravel pathways, capturing the tranquil evening ambiance.
Cabin in Greene
4.95 out of 5 average rating, 128 reviews

"Wilma" - Riverfront Cabin

This recently improved riverfront cabin, has a style all its own. Open entertainment space extends on to the 40 ft long deck. The many windows and doors allow nature in, complementing the locally sourced live edge countertops in the kitchen. Beautiful views are seen of the lush landscaping, river and distant mountain, from every room. The kitchen offers all ammenities, such as a dishwasher, large french door style refrigerator, and a ton of storage along with ample countertops.

Guest favourite
A golden sunset casts warm light on trees, illuminating their autumn leaves in shades of orange and yellow. A wooden fence separates the foreground from a serene landscape of rolling hills and greenery, inviting exploration of the natural surroundings.
Apartment in Port Crane
4.99 out of 5 average rating, 71 reviews

Welcome to Osborne Creek!

Something different. Country setting 23 acres and only 10 minutes to downtown Binghamton. Newly renovated spacious efficiency apartment with ALL the comforts of home, whether your staying for 1 night or many nights, our goal is to make you feel like you are on vacation. Linens, pots, pans, towels, washer/dryer provided. Offering accommodations for people traveling with horses too at some point. This is farm and farmhouse with its own private efficiency apartment.

Top Guest favourite
Home in Deposit
5 out of 5 average rating, 106 reviews

Catskill Snuggle Spot-Bedrm Fireplace-Sauna-HotTub

Enjoy a winter escape in the Scandi Farmhouse! Snuggle by the bedroom gas fireplace. Relax in the Finnish sauna, take a plunge in an antique cold tub. Melt away stress in the Hot Tub. Enjoy a roaring campfire in the Solo Stove. 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.

Top 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, 196 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, 411 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.

Guest favourite
The exterior of the garden studio is framed by vibrant greenery, featuring a kayak resting against the roof. Large glass doors reflect the surrounding foliage, while colorful flowers and plants create a welcoming garden space. A secure area for pets is visible alongside.
Guesthouse in Windsor
4.89 out of 5 average rating, 28 reviews

Susquehanna Selfie Studio

Shabby chic riverfront photo studio apartment. Perfect for a quick weekend getaway and great for longer remote work stays. Less than 10 mins from NY 17 and 15 mins from I-81. Fishing and boating access, 1000+ acres NY/PA game lands nearby. 10 mins from Animal Adventure, 7 mins from Aaronic Priesthood Restoration Site. 25 mins from Binghamton University and area shopping centers

Popular amenities for Windsor holiday rentals

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