Holiday houses 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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Guest favourite
A charming cabin is set beside a serene pond, featuring a colorful fountain that lights up the water. Soft string lights illuminate the outdoor space, creating a cozy atmosphere amidst the surrounding trees.
Cabin in Wrightsville
4.98 out of 5 average rating, 224 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

Top Guest favourite
A tranquil porch is featured with two wooden rocking chairs positioned side by side. The floor is made of polished wood planks, and the railing provides an open view of the surrounding greenery. Sunlight filters softly through the nearby trees.
Home in York
4.93 out of 5 average rating, 102 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 favourite
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, 179 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 favourite
A wooden gate adorned with longhorn decorations frames a vast green field, leading towards rolling hills in the distance. The sky above is clear with a few fluffy clouds, enhancing the serene rural landscape.
Farm stay in New Park
4.96 out of 5 average rating, 160 reviews

Dusty Roads Ranch

Relax, rejuvenate and enjoy the scenery. This is a impeccably maintained private property in southern York county, Pennsylvania. Located in a convenient location from York, Lancaster, and Baltimore. Close by to county parks, breweries/wineries, and farms. Enjoy your sunset fireside on our lush horse farm or take a walk through our trailed woods. Massage therapy available upon request. We recommed 4-wheel drive for winter bookings. There is a camera that faces the driveway as you pull in.

Top Guest favourite
Home in Pequea
4.97 out of 5 average rating, 107 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 favourite
Cabin in Millersville
4.99 out of 5 average rating, 142 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 favourite
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, 259 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 favourite
The exterior of a charming yellow house is showcased, featuring red shutters and a red front door adorned with a wreath. A front porch with steps leads to the entrance, and vibrant flower pots are positioned on either side, complemented by a large tree's canopy overhead.
Home in Marietta
4.97 out of 5 average rating, 127 reviews

Little Yellow House Marietta PA

Experience a part of early Marietta history in this 1807 "Yellow House" that was expanded and newly updated to offer the charm of its log home. TRAINS!!!!Across the street is a freight train line service. The trains are random at all hours. They are briefly loud. Otherwise this a lovely space situated along the Susquehanna. There are several restaurants close by. Close to Hershey and Lancaster Amish Country. Bike trail across the street. Cayaking on the Susquehanna River.

Top Guest favourite
A cozy living area is highlighted by a gas stove fireplace set within a charming brick wall. Light green walls complement a soft area rug and a round wooden coffee table. Two comfortable chairs are positioned invitingly, and natural light flows through large windows.
Home in Lancaster
5 out of 5 average rating, 194 reviews

Cozy cottage on beautiful dairy farm in Strasburg

Tranquil. Refreshing. Restful. These are the perfect words to describe Graystone Cottage, located on a working dairy farm just outside the quaint historic town of Strasburg in Lancaster County, PA. Built in 1753, this 1000 square feet, newly restored limestone cottage was the original settlement home on the 135-acre homestead. Boasting a French country esthetic, this little darling has the most captivating views of rolling hills, a brook, and lush green farmland.

Top Guest favourite
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
4.97 out of 5 average rating, 153 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

Guest favourite
The exterior of a charming house features a light grey facade with white trim and a pitched roof. Symmetrical windows with shutters enhance the inviting appearance. A well-maintained front yard with shrubs and a pathway leads to the entrance, complemented by a lamp post.
Home in Red Lion
4.85 out of 5 average rating, 130 reviews

Wise Ave—Home Sweet Home/Main&Spacious Loft

Great location! A short drive from local restaurants like Lion’s Pride (café) and The Great American Saloon, also from gas station and convenience stores like Giant and Weis. Enjoy a peaceful stay in a quiet location in town and free WiFi. Whether you’re looking for a long-term stay or need a quick stop for your journey, ideal for families, groups, or couples looking for a roomier stay. Our home is comfort and ease in mind.

Guest favourite
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
4.92 out of 5 average rating, 150 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 holiday rentals

  1. Airbnb
  2. United States
  3. Pennsylvania
  4. York County
  5. Windsor