
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.

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.

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.

DEER RUN LODGE
Tucked away in the beautiful mountains of NE PA. Access to PA State Game land #299. 3 ski resorts within an hour drive. O&W snowmobile trail within a short drive. Fly-fishing on the West Branch of the Delaware River within 4 miles. Covered Deck, Gas Grill, Fire pit for cozy campfires. 20 minutes from 2 quaint towns offering restaurants, theaters, grocery stores. The weekend getaway place to read a book, hunt, fish, bird watch. NO PETS ALLOWED except for well trained service or hunting dogs.

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.

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.

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.

Cozy/Chic Cabin Binghamton NY
Retreat, isolated get-away but nearby town. This cozy cabin is rustic with some chic flair, decor & recent updates. Privately set on 2 wooded acres & near town. 2 stone fireplaces, indoor Jacuzzi tub, 2 1/2 BA, 3-4 BR & 7 person outdoor hot tub. Excellent WIFI, kitchen & dining. Picnic, grill & fire pit. Great fall foliage, near skiing, near hiking, boat launch. Fully outfitted, just bring yourself!! Willing to accommodate guests—ask!!

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
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

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Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Cornell University
- Bethel Woods Center for the Arts
- Elk Mountain Ski Resort
- Greek Peak Mountain Resort
- Claws 'N' Paws
- Woodloch Resort
- Pocono Mountains
- Three Hammers Winery
- Upper Delaware Scenic and Recreational River
- Six Mile Creek Vineyard
- Ithaca College
- Steamtown National Historic Site
- Lackawanna State Park
- The Andes Hotel
- The Settlers Inn
- Newton Lake
- Villa Roma Resort
- Electric City Aquarium
- Ross Park Zoo





