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Holiday rentals 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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Top guest favourite
A modern kitchen and dining area are presented with a large island and a dining table surrounded by six chairs. Natural light fills the space through large windows, complementing the neutral color palette. Fresh flowers are arranged in a vase on the countertop.
Home in York
4.94 out of 5 average rating, 358 reviews

The Inn- Newly Renovated Designer Furnished

Newly renovated home features all of the modern amenities families enjoy. A large island for entertaining, a dining table seating 8, large living room, a bright sunroom with plenty of seating, as well as a sun porch with a bistro table & chairs, outdoor seating, & 3 spacious bedrooms upstairs each has a queen size bed. The home is a minute's walk from our popular home decor boutique, Gray Apple Market. A 10 minute drive to downtown York & other popular destinations such as the York Fairgrounds.

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, 180 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
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
5 out of 5 average rating, 163 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 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, 127 reviews

Waterfront Terrain- Relax, Unplug, Enjoy!

This 2,000 sq. ft. House is perfect for families looking to RELAX and UNPLUG in the countryside of Lancaster County while still being close to major attractions. 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 in basement or lounge in open concept living room with your favorite beverage can also be experienced when you choose to stay at the Waterfront Terrain!

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, 247 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, 237 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.

Guest favourite
A wooden deck is accessed by a set of steps, featuring a rail and a covered area above. The house showcases a mix of green siding and natural wood elements, highlighted by a circular window and skylights that allow sunlight to illuminate the space.
Bungalow in Columbia
4.98 out of 5 average rating, 112 reviews

The River Bungalow @ Manor Station

Take it easy at this unique and tranquil getaway. The entire home has been newly renovated with thoughtful touches and an eclectic feel. Conveniences include a wood stove, sleep number mattress, Viking gas stovetop/oven, deck facing river with propane grill, a covered carport entry, and a 180* river view at the top of the property! We are very excited to welcome guests and hope to provide a memorable experience for all. Well behaved dogs welcome upon request. Wood stove $25/night.

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, 147 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

Superhost
A spacious bedroom is brightened by natural light from two large windows. The bed features a soft, textured blanket and fluffy pillows. A cozy accent chair complements the room, while a dark wood dresser adds storage space. Light pink walls enhance the calm environment.
Guest suite in York
4.87 out of 5 average rating, 177 reviews

Quiet INNspiration Suite

Private suite in a quiet neighborhood just outside the city. The unit is tastefully decorated, sparkling clean and includes a very comfortable bedroom, full bathroom, & mini eating area. There is a small kitchenette with a mini fridge and freezer, a microwave, toaster oven, Keurig machine and electric kettle with all essential kitchen items. It's well equipped for short as well as long stays.

Top guest favourite
A comfortable living area features a neatly arranged sofa and armchair, with a round coffee table at its center. Natural light enters through large windows, while a stone fireplace adds a rustic touch. A television and decorative elements complement the warm ambiance of the space.
Home in York
4.99 out of 5 average rating, 184 reviews

Sunrise on Wilson

Welcome! Enjoy a cup of Lancaster County coffee on the back porch and watch the sun rise over the pastures. Our quiet location is ideal for those who wish to relax and unwind. Great for families or those traveling for business alike! We are conveniently and centrally located between York (9 mi.) Lancaster (20 mi.), Hershey (30 mi.), Gettysburg (40 mi.) and Baltimore(60 mi.).

Guest favourite
The living area features light grey walls complemented by hardwood flooring. A cozy armchair and a sofa provide seating, while a round dining table with chairs accommodates four. Two windows invite natural light, and a decorative area rug adds warmth to the space.
Flat in Mountville
4.95 out of 5 average rating, 680 reviews

Mountville: The Penny House

THE PENNY HOUSE! Renovated and decorated 2 bedroom apartment. My wife and sought to create a modern, comfortable clean and light feel. The Penny House was once a carriage house for horses; years later the second floor was converted into two unique living spaces. (Note: See my other listing if the Penny House calendar is full) Easy access to many local destinations.

Top 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, 192 reviews

The Roundtop Chalet (romantic couples retreat)

We invite you to experience this Charming Cabin!!! The perfect spot to celebrate anniversaries, birthdays or any special occasion! A Romantic couples getaway with a Cozy Fireplace, Hot Tub, and endless Lattes with our Breville touch Espresso machine!

Popular amenities for Windsor holiday rentals

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