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Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

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

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Guest favourite
A spacious wraparound front porch is lined with white railing, casting shadows on the wooden floor. Lush greenery is visible in the surrounding area, with a glimpse of the street and a fire hydrant in the distance.
Home in Binghamton
4.95 out of 5 average rating, 474 reviews

Quiet Private Apartment Park Setting West Side

Last minute? 1-2 nights? Please inquire!! 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 min drive. Close to BU. A variety of restaurants, bars, shops, antiques in the area.

Guest favourite
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
4.81 out of 5 average rating, 195 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
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
4.97 out of 5 average rating, 156 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, 112 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, 110 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.

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, 285 reviews

Rink Side Cabin at The Farm Rink

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, 191 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.

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
4.94 out of 5 average rating, 118 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.

Top 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
5 out of 5 average rating, 63 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
A waterfront property is showcased with a raised structure featuring a large deck and steps leading up to the entry. The exterior is clad in neutral siding, while the area underneath provides a shaded space. An American flag gently flutters in the breeze.
Home in Kirkwood
4.92 out of 5 average rating, 193 reviews

Susquehanna River House

Welcome to the Susquehanna River House — a peaceful, fully remodeled 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.

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, 401 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
A serene pond reflects the clear blue sky, framed by lush greenery and tall grasses. A floating dock is visible on the water, surrounded by gently rolling hills and distant trees, creating a peaceful natural landscape in a countryside setting.
Bungalow in Windsor
4.89 out of 5 average rating, 104 reviews

Ernie’s Retro Retreat

Take it easy at this 1980s inspired bungalow in a peaceful country setting. The interior is beautifully decorated with retro accents and modern comforts. Enjoy beautiful views from every room of rolling hills and forests. There’s plenty to do at the half acre fishing/ swimming pond and this location is close to Hawkins Pond and hiking trails.

Popular amenities for Windsor holiday rentals

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