Holiday rentals 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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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, 361 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

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
4.94 out of 5 average rating, 480 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.

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.
Flat in Greene
4.98 out of 5 average rating, 170 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, 121 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
4.89 out of 5 average rating, 166 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.

Top guest favourite
Cabin in Montrose
4.98 out of 5 average rating, 133 reviews

Cozy Cabin with Mini Goats & Hot tub Starlink WiFi

Here you can relax with the whole family or it’s a perfect getaway for 2. From Spring to late fall we’ll have mini goats and free range rabbits & chickens. The creek is perfect for tubing on a hot summer day.Have a picnic in the trees next to the water.Just a mile away is an ice cream/petting zoo and greenhouse with amish gifts. Next door is our operating hobby farm with donkeys, sheep alpacas, goats and chickens.If you’re looking for a nice relaxing retreat, we have what you’re looking for.

Top guest favourite
A charming cabin is positioned on a grassy knoll, showcasing a wraparound porch with wicker chairs and decorative elements. The structure features a combination of stone and wood materials, with a sloped roof and large windows allowing for natural light.
Cottage in Oxford
4.99 out of 5 average rating, 395 reviews

Beaver Palace Studios and Estates relaxing getaway

Your total getaway from the city and/or hectic life. We offer a very private and personal space for you to unwind and relax Everything on the property is handmade/built by owners. The grounds are very private. There is an abundance of wildlife and 50+ acres of private grounds to explore. Both owners are artists and world travelers. This stay is casual, relaxing and a real get away from it all. Hosts just down the lane for any assistance. Please book accurately # of people and # of pets.

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, 287 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
Home in Narrowsburg
4.92 out of 5 average rating, 474 reviews

Cutest Little House in Narrowsburg

Relax in an idyllic wooded setting with 1000 feet of totally private river frontage, yet a 5 minute drive to Narrowsburg's restaurants and shops. If you like nature, privacy, history, vintage decor & design, this quaint 1950s cottage is for you. Hiking & campfires • Clawfoot tub • Front & back porches • Hummingbird & bunny watching • Den & WiFi • Peace & quiet • All included in your stay! Hundreds of 5-star reviews say it all. IG: #luxtonlake #tenmileriver #cutesthousenarrowsburg

Top guest favourite
Cabin in Walton
4.94 out of 5 average rating, 206 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
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, 194 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
The vibrant sunset casts a warm glow over Tingley Lake, reflecting shades of orange and pink on the water's surface. A wooden dock extends into the lake, surrounded by lush greenery and a visible kayak. A flag gently flutters in the foreground.
Flat in New Milford
4.9 out of 5 average rating, 216 reviews

Tingley Lake Super Suite

The house includes a master suite and 1 bedroom, 1.5 bathrooms, a full kitchen / living area. There is a walk out patio, spacious deck area and dock for swimming, canoeing, kayaking or paddleboarding in beautiful Tingley Lake.Continental breakfast (cold and hot cereal and / or pastry with coffee and fruit) is available for stays less than 3 nights. Private entrance and self-check in.

Popular amenities for Windsor holiday rentals

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