Holiday rentals in Windsor

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Windsor

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

%{current} / %{total}1 / 1
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, 227 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 comfortable bedroom features a wooden bed with a blue and white patterned bedspread. Decorative pillows add texture. A bedside lamp sits on a white nightstand. A chair is positioned nearby, and two doors lead to additional storage space.
Flat in York
4.89 out of 5 average rating, 196 reviews

Quiet INNspiration Cottage

Private small apartment in a quiet neighborhood close to the city. It has a separate entrance on lower level with tile floors. The unit is sparkling clean and includes a very comfortable bedroom, bathroom, living room & eating area. There is a kitchenette with a mini fridge and freezer, a microwave, hot plate, toaster oven and coffee & tea maker with all essential kitchen items. There is also a large capacity washer and dryer in the unit. It's fully equipped for short as well as long stays.

Top guest favourite
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
4.93 out of 5 average rating, 103 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 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 out of 5 average rating, 109 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!

Guest favourite
Cabin in York
4.92 out of 5 average rating, 197 reviews

Private Home on Rustic Farm

The Loomis House is a cozy loft cabin on private property. Free from the distractions of the outside world, but with all the conveniences of modern life. Deep Run Farm enjoys a quiet setting on the grounds of a colonial-era farm. Some of the original structures on the property date to the 1800s. This perfect rustic setting is conveniently close to shopping and major highways (US 30 and Interstate 83). Come to disconnect and enjoy the wildlife, or just for a quick lay-over in a quiet space.

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 rustic cabin is nestled among trees, elevated on a wooden deck. The vibrant red roof contrasts with the surrounding greenery. Four red chairs are arranged on the deck, providing a view of the natural landscape. Sunlight filters through the leaves, creating a serene ambiance.
Cabin in Airville
4.98 out of 5 average rating, 113 reviews

"ON THE ROCKS CABIN" the perfect getaway for 2!

Cabin is very charming, but rustic. Kitchen has full size frig, microwave, toaster oven, hot plate, toaster+ keurig. Coffee, condiments, soap & shampoo provided. There is a gas grill. Guests provide their qs sheets, towels, campfire wood & drinking water. A variety of dvd’s & games, hot water in & outside shower & tub. Tubes for floating provided, swim your own risk. Fire pit, creek is stocked. Steps to deck overlooking the creek.Trash goes home with guests, smoking on the decks only.

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, 260 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, 129 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
The charming stone house is bathed in warm light, highlighting its inviting windows. Lush landscaping features a gravel pathway and seating areas, with a fire pit surrounded by chairs. Soft lighting strung between trees creates a cozy ambiance in the outdoor space.
Cottage in Stevens
5 out of 5 average rating, 125 reviews

Cozy Cottage •HOT TUB • FIRE PIT• Peaceful Getaway

🌾 Welcome to Your Cozy Farm Retreat A peaceful, private guest cottage located on our small, quiet farm — complete with your own private hot tub, fire pit, and beautiful views. This is the perfect escape to relax, recharge, and enjoy the countryside. Sip coffee overlooking the fields, unwind in the hot tub under the stars, or explore the local farms, breweries, and trails nearby. Perfect for couples or solo travelers seeking a quiet getaway.

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, 151 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