
Holiday rentals in Windsor
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Top-rated holiday rentals in Windsor
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⭐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

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.

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.

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!

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.

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.

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.

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.

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.

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.

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

Creekside of the Moon A-frame Cabin
Creekside of the moon A-frame glamp. Float, fish and play in the Catskills. Glamp on the Charlotte Creek in a newly built modern tiny a-frame. Sleep under the full moon. A giant moon light hangs over the bed(s) with a stunning reflection in the window at night over the creekview. Perfect for a romantic getaway, fishing trip, or glamping spot in the Catskills. Close to Cooperstown, NY IG @aframe_moon
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Charming cabin in the woods. Fire pit and Fiber!

Rivers Edge

Winter Get-away w/ Great Views-King Bed-Pool Table

The Porch at Alchemized Acres

Nature Escape to Beautiful Upstate NY

Charming 120-year-old farmhouse by the creek.

Comfort Meets Convenience | Easy Highway Access

45 Acres of peace, quiet, and outdoor fun!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
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- East River Holiday rentals
- Mississauga Holiday rentals
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- Jersey Shore Holiday rentals
- Cornell University
- Elk Mountain Ski Resort
- Bethel Woods Center for the Arts
- Greek Peak Mountain Resort
- Chenango Valley State Park
- Pocono Mountains
- Claws 'N' Paws
- Lackawanna State Park
- Woodloch Resort
- Ithaca College
- Six Mile Creek Vineyard
- Upper Delaware Scenic and Recreational River
- The Andes Hotel
- Three Hammers Winery
- Steamtown National Historic Site
- Newton Lake
- The Settlers Inn
- University of Scranton
- Electric City Aquarium




