Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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Top guest favourite
A cozy living area features a stone wall accentuated by natural light from multiple windows. Two upholstered armchairs and a sectional sofa are arranged around a fireplace, which is complemented by a mounted television above a wooden shelf. A floor lamp stands nearby.
Barn in Quarryville
5 out of 5 average rating, 141 reviews

The Barn at Locustwood Farm

Come enjoy your stay in our 1900 sq ft 19thcentury restored stone barn. We’re 15 minutes from Sight and Sound and the shops at Strasburg. With lots of trails and the Susquehanna River close by, your family can spend many hours hiking in southern Lancaster County. Experience the local Britain Hill Vineyard,coffee,and ice cream shops nearby. The charming city of Lancaster with its many authentic restaurants is only a 20 minute drive. We would love to have you come and enjoy the barn stay with us

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, 189 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 rustic wall features two framed art pieces amidst a beautifully textured white brick backdrop. A wooden shelf displays decorative items, including candles, bottles, and colorful glass orbs, creating an artistic focal point in the space.
Loft in York
4.94 out of 5 average rating, 191 reviews

Cozy up in “The Loft” w/artsy vibe. 1 min to Hosp.

2 blocks to York Hospital. Extended stay discount offered. The property is full of art and beauty! I love living here, and opening up the "Loft” of my home to guests! This is my second listing on my property. The Loft space is quite sizable, 750 sf, with an all open floor plan. Property built 100 years ago...and as they say, they're just not built like this anymore! It is bright and cheery by day, and private by night. The "Loft” space has a funky city vibe with the open floor plan. CHARMING!

Guest favourite
The two-story farmhouse features a classic red brick exterior with a covered porch. Large windows provide ample natural light. A sprawling tree is situated nearby, complemented by lush green grass that surrounds the home, adding to the serene rural ambiance.
Farm stay in Conestoga
4.98 out of 5 average rating, 182 reviews

Cozy Hilltop Farmhouse

Our cozy farmhouse is your home away from home! This Lancaster county farm is nearly 100 acres of rolling hills and will provide you with a peaceful farm atmosphere with amazing sunrises and sunsets! Perfect for a romantic getaway. There is 1 bedroom with a queen size bed, attached full bath. 1 pullout couch in living room. 1/2 bath on first floor. Come experience the rich heritage of Amish country while checking out the many nearby Lancaster attractions. Also, say hi to our 20 beautiful hens!

Top guest favourite
The living area features high, exposed wood beams and large windows that fill the space with natural light. A cozy white wood-burning stove is positioned near a leather sofa, complemented by a collection of firewood nearby, creating a warm and inviting setting.
Home in Columbia
4.99 out of 5 average rating, 110 reviews

Restored Distillery | Sunroom + 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 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, 167 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 grand historic home is showcased, featuring a prominent facade with a steep staircase leading to the entrance. The red brick steps are flanked by carefully manicured greenery, while American flags are displayed, adding a touch of charm to the structure.
Guest suite in Marietta
5 out of 5 average rating, 254 reviews

Private suite - The Cassel House of Marietta

Welcome to The Cassel House of Marietta, where historical charm meets modern luxury! Guests enjoy a private suite which includes a bedroom, bath, kitchenette, large living room, and a spacious patio. Reliable Wi-Fi, Cable TV, plush towels, and outdoor games are also included. The Cassel House is conveniently located between Lancaster, Hershey, York and Harrisburg. Experience the charm of a historic home built in 1885 with the proximity to major destinations that tourists and locals enjoy!

Top guest favourite
A modern kitchen features light gray cabinetry, a large island with wooden accents, and stainless steel appliances. Natural light fills the space through large windows, complemented by subtle pendant lighting. A small dining area is visible, inviting casual meals and gatherings.
Guest house in Columbia
4.97 out of 5 average rating, 243 reviews

The Carriage House-Serene, Rural Setting w/Firepit

Welcome to our newly renovated large 1-bedroom suite, located above our three car garage in a stunning rural area with plenty of outdoor space. It is perfectly situated near numerous attractions, and it offers a comfortable and quiet retreat from the hustle and bustle of city life. We, The Host's, live in the main house of the property, but are very respectful to your privacy. Whether you're in town on business or seeking a relaxing retreat, we know you will enjoy this charming place.

Top guest favourite
A comfortable living room is furnished with a light-colored sofa and a plaid accent chair. Natural light fills the space through large windows adorned with sheer curtains. A wooden coffee table and lamp are positioned near a TV setup, creating a cozy, inviting area.
Flat in Millersville
4.89 out of 5 average rating, 539 reviews

Comfortable one bedroom with parking

This is a first-floor, one-bedroom apartment with full eat-in kitchen, and living room with Netflix-only t.v. Terrific for budget-conscious travelers who like to save by eating in; families, business travelers and visitors of Millersville University. There is a small bathroom off the bedroom with shower. A private entrance to come and go as you please. Located in a safe neighborhood, this secure apartment is clean and offers plenty of off-street parking. Just 5 miles from Lancaster City.

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, 149 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 favourite
An outdoor courtyard presents a stone fireplace framed by warm lighting from string lights. Comfortable seating is arranged around a decorative rug, with a small round table nearby. Large windows and a wooden door promote a connection to the interior space.
Cottage in Columbia
4.98 out of 5 average rating, 123 reviews

The BirdHouse. Dog friendly. Accommodates 2 guests

Enjoy the coziness of the BirdHouse. Our kitchen has the necessities to cook. We provide olive oil, spices, salt and pepper, farm fresh eggs, coffee filters, and trash bags. For the bathroom we provide starter shampoo and conditioner, toilet paper, and of course the towels. Linens provided also. Enjoy the courtyard area with its gas fireplace and seating area. Cook on the gas grill and enjoy a meal at the bistro table. Please come and relax!

Guest favourite
Place to stay in Yorkana
4.92 out of 5 average rating, 123 reviews

Unique Shoe-Shaped House w/ Hot Tub & Firepit

👞 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 and Hot Tub!

Popular amenities for Windsor holiday rentals

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