Vacation rentals in Windsor

Find and book unique accommodations on Airbnb

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
Cabin in Wrightsville
4.98 out of 5 average rating, 252 reviews

The Roundtop Chalet (romantic couples retreat)

Indulge in a getaway to our charming cabin, the perfect retreat for all your special celebrations - be it anniversaries, birthdays, or simply a much-needed escape from routine. Perfectly designed for romantic getaways, this cabin seamlessly blends rustic charm with modern comforts. Savour the warmth of a cozy fireplace, unwinding in a hot tub,and indulge with unlimited lattes, crafted by our Breville Touch Espresso Machine. Embrace serenity at its finest and make memories that will last forever

Guest favorite
A circular gathering area is positioned on a gravel surface, featuring four wooden Adirondack chairs arranged around a stone fire pit. Lush green grass surrounds the space, with trees and a building visible in the background under a partly cloudy sky.
Home in York
4.92 out of 5 average rating, 112 reviews

Peaceful Farm, Pond + Fire Pit Close to Lancaster

Escape to our charming countryside retreat! Relax by the large koi pond and dock, surrounded by lush greenery and soothing streams. Enjoy catch & release fishing! Explore acres of private land for peaceful walks. Nearby, John Rudy Park offers hiking and horseback riding trails. Only 20 minutes from quaint Lancaster, PA. Easy access to I-83 and Route 30. Enjoy the best of both worlds with tranquility and accessibility to restaurants and shops, only 10 minutes away. Perfect rejuvenating getaway!

Top guest favorite
A warm living room is highlighted by wooden beams overhead and natural light streaming through French doors. A cozy sofa is positioned beside a rustic coffee table adorned with decorative items. Soft greenery is placed on surfaces, enhancing a serene environment.
Cabin in Railroad
5.0 out of 5 average rating, 135 reviews

The Creek House: Waterfront with Hot Tub & E-bikes

Featured on Magnolia Network’s “In with the Old” Season 1, Ep. 2 (HBO Max), The Creek House is a hidden gem in the heart of Railroad, PA. Nestled between the NCR Rail Trail and two flowing creeks, this location offers both adventure and relaxation at its finest. Explore the over 40 mile bike trail via E-bike, soak in the hot tub while you enjoy sounds of the creek, or ride the train right through the front yard! This idyllic cabin features professionally designed spaces that are sure to please!

Top guest favorite
A bright kitchen features white cabinetry and open shelving with decorative items. A round dining table is set with wooden chairs, complemented by a floral centerpiece. Natural light streams through sliding glass doors, creating a warm and inviting cooking space.
Farm stay in Lancaster
4.98 out of 5 average rating, 501 reviews

Luxury Farm Cottage - hot tub & patio

Welcome to the Inglewood Farm! Inspired by Old European design and the Cotswolds of England, this gives you a luxury farm stay in a sweet 2-bedroom cottage. Tucked in a peaceful wooded corner on our 20-acre 1700’s farmstead, you can visit the animals, see the rhythm of our family farm life, and enjoy being in nature. New - Hot tub 2025! Located 3 miles south of Lancaster, we are 15-20 minutes within major attractions including Sight & Sound Theatre, Amish Country, Strasburg, and Lititz.

Top guest favorite
Home in Columbia
4.96 out of 5 average rating, 125 reviews

Restored Distillery | Sunroom + Outdoor Sauna

Stay at this historic c. 1755 stone house that was once an operating distillery, now reimagined with stunning design and eco-friendly geothermal power. The showstopper is the dramatic two-story sunroom with stone walls, artwork, and natural light. Enjoy a chef’s kitchen, Peloton bike, and beautifully furnished living spaces. Outdoors, relax in the BRAND NEW top-of-the-line sauna (installed Fall 2025). 15 min to Lancaster, 40 min to Hershey, and easy drives from Baltimore, Philly, DC, and NYC.

Top guest favorite
A cozy sleeping area features a spacious bed adorned with varying patterned bedding. A side table holds a small lamp, while a comfortable chair is positioned beside a dining table for two. Warm lighting enhances the inviting atmosphere, complemented by a scenic artwork on the wall.
Guest suite in Red Lion
4.99 out of 5 average rating, 189 reviews

Private suite with kitchenette

Private suite with kitchenette, full bath, private entrance, and free on-street parking in beautiful rural area. Quiet neighborhood. Centrally located: 30 min. to Harrisburg or Lancaster; 1 hr. to Baltimore or BWI airport; 2 hours to Philadelphia. Ski Roundtop is only 30 minutes away! Hiking and biking on local rail trail. Happy to provide recommendations for restaurants and things to do in the area. Enjoy the Keurig coffee maker, microwave, and mini-fridge; snacks and bottled water provided.

Top guest favorite
A historic stone exterior is showcased, featuring a dark green door adorned with a circular wreath. Two rectangular windows with individual panes complement the textured stone walls. Planters with greenery are seen beneath the windows, adding a touch of nature to the entrance.
Home in Pequea
4.97 out of 5 average rating, 117 reviews

1700’s historic waterfront cottage

Be a part of history while staying on this waterfront property of the Ironmaster's Mansion. The two-story stone guesthouse, steps away from the mansion, was built in the year 1715. The timeless character of the home, paired with the peaceful property creates an escape that feels like you've gone back in time, all while being only 20 minutes outside of Lancaster City. The mansion was home to the first treasurer of the US, General Edward Hand’s daughter, and President Buchanan’s fiance.

Top guest favorite
A spacious living area features a high, wood-paneled ceiling and a prominent stone fireplace, providing warmth and ambiance. Multiple large windows allow natural light to brighten the room, while comfortable seating arrangements encourage relaxation and conversation.
Cabin in Millersville
4.99 out of 5 average rating, 156 reviews

Waterfront Terrain- Relax, Unplug, Enjoy!

RELAX and UNPLUG in the countryside of Lancaster County at this 2,000 sq. ft. house perfect for families, friends groups, and Bridal Party!This cabin is nestled between two hills, making it the most serene spot in the area. You will enjoy hearing the gentle rustles of the creek or spot a deer, or eagle! Play ping-pong or corn hole, in basement or lounge in open concept living room with your favorite beverage. Make the best memories when you choose to stay at the Waterfront Terrain!

Top guest favorite
The exterior view of the log cabin is set amidst a lush, wooded landscape. A stone path leads to the cabin, which features a spacious outdoor deck adorned with plants and seating. The serene ambiance of the surrounding nature invites relaxation.
Place to stay in Airville
4.98 out of 5 average rating, 284 reviews

Waterfront Log Cabin with Hot Tub

Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

Top guest favorite
A charming blue cottage is set against a backdrop of greenery. The entrance features a dark blue door adorned with a decorative wreath. A spacious deck is visible, framed by trees and a small landscaped area with a potted plant.
Cottage in Conestoga
4.98 out of 5 average rating, 160 reviews

Creswell Cottage/no pets

This quaint little secluded cottage. Enjoy beautiful sunrises. Sit on the deck and watch the deer, turkey, rabbits squirrels, and plenty of birds. You can even hear bullfrogs croaking from the neighbors water garden. No pets allowed Enjoy staying among the beautiful countryside of Lancaster County Area attractions include- -turkey hill/enola low grade and Columbia northwest rail trails -site and sound theater -the Fulton theater -Lancaster Central Market

Top guest favorite
The exterior of a transformed tobacco barn is depicted, featuring a blend of red siding and a stone foundation. Lush landscaping with greenery and decorative features can be seen in front of the structure, which is framed by a clear blue sky.
Barn in Columbia
4.98 out of 5 average rating, 114 reviews

The Barn at Broadleaf Bend

Nestled in Lancaster County stands a magnificent 1750's Amish tobacco barn, thoughtfully transformed into a unique Airbnb experience. This historic structure, once the largest tobacco barn in the area, maintains its authentic charm while offering modern comforts. This extraordinary accommodation offers a rare opportunity to experience Lancaster County's agricultural history while enjoying the perfect base for exploring all the region has to offer.

Guest favorite
The unique exterior of the Shoe House is prominently displayed, featuring a smooth, white plaster finish contrasted by gray accents. A bright yellow door serves as an inviting entrance, framed by small windows. Lush landscaping and a well-maintained yard contribute to the charm of this landmark.
Place to stay in Yorkana
4.93 out of 5 average rating, 173 reviews

Iconic "Shoe House" w/ Hot Tub, Firepit & Arcade!

👞 Welcome To The Haines Shoe House 👞 Featured On HGTV & The Amazing Race, Our Incredibly Unique Airbnb Is Nestled Along The Historic Lincoln Highway and Sits Beside Beautiful Pennsylvania Farm Fields! Recently Designated A Historic Landmark, We've Meticulously Designed The Shoe House For Our Guests To Feature A Wood-Burning Outdoor Firepit, Charcoal Grill, Outdoor Dining, Hot Tub, 300 Game Arcade Machine & Foosball!

Popular amenities for Windsor vacation rentals