Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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

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Top guest favorite
The spacious great room features high wooden ceilings supported by exposed beams. Large windows allow natural light to fill the space, which includes a cozy seating area with a light-colored sofa, a dining table, and a fully equipped kitchen in the background.
Barn in Jermyn
4.98 out of 5 average rating, 216 reviews

Restored Barn - 44 Acres, 100 Acre Lake

Reconnect with nature at this unforgettable retreat. Escape to our renovated barn on a 44-acre eco-paradise. Experience modern farmhouse living with 25-foot ceilings, a great room with beautiful views, fully equipped kitchen, king-size bed in giant loft bedroom, and cozy gas stoves. Hike, kayak or fish on the 100 acre lake, forage for wild berries and ramps in season, or go skiing at Elk Mountain right down the road. One-of-a-kind serenity and rustic, natural luxury in Pennsylvania's wilderness.

Superhost
A tiny cabin with a unique Japanese-inspired design is nestled among tall trees, accompanied by a gravel pathway and a small fire pit. The cabin's natural wood exterior blends with the forest surroundings, creating a serene atmosphere beside a flowing brook.
Cabin in Downsville
4.88 out of 5 average rating, 344 reviews

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.

Top guest favorite
The A-frame cabin is nestled among trees, featuring a wooden deck and wide glass doors that open to the interior. A private hot tub is positioned nearby, providing a relaxing outdoor space surrounded by nature.
Cabin in Damascus
4.98 out of 5 average rating, 264 reviews

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.

Top guest favorite
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, 159 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 favorite
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, 127 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.

Top guest favorite
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
5 out of 5 average rating, 405 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.

Top guest favorite
Cabin in Walton
4.95 out of 5 average rating, 251 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 favorite
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, 146 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 favorite
Home in Deposit
5 out of 5 average rating, 123 reviews

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.

Top guest favorite
Home in Narrowsburg
4.92 out of 5 average rating, 133 reviews

Modern Secluded Retreat

Escape to the center of 11+ acres of woods, water, and dark starry skies—under 2 hours from NYC. Walls of windows pull the outside in, with a stream, pond, and constant wildlife just beyond. Warm up by the fireplace, unwind in the open living space, and sleep deep in a king bed. A large jetted bathtub, bonus half bath, and a flexible bonus room with pool table and ping pong table on heated floors round it out. Peaceful, private, and made for slowing down.

Guest favorite
A rustic cabin is nestled among lush trees, featuring a metal roof and warm, inviting windows. Soft lighting from the windows enhances the natural surroundings, while a stone walkway leads to the entrance, blending harmoniously with the forest landscape.
Place to stay in Downsville
4.88 out of 5 average rating, 230 reviews

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.

Guest favorite
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
4.9 out of 5 average rating, 116 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.

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