Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

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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.
Apartment in York
4.89 out of 5 average rating, 187 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.

Superhost
A modern living area is featured with a gray sofa adorned with colorful throw pillows. A blue area rug lies on the floor, complementing the light wood tones. Large windows allow natural light to fill the space, and a small round table with orange chairs is visible.
Apartment in York
4.84 out of 5 average rating, 219 reviews

Weekend Away Studio

Located a block from Continental Square, this historical building is cute and comfortable. Perfect for a weekend downtown, the unit offers city views from a corner room with lots of natural light. This studio apartment is equipped with a full kitchen, bathroom, washer and dryer. Kitchen wares, linens, pillows and bath towels are provided. Please read all details before booking. We look forward to hosting you! If your dates are already booked, check out our profile for another downtown space.

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, 162 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, 244 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.
Guesthouse in Columbia
4.97 out of 5 average rating, 235 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
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
4.96 out of 5 average rating, 109 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
Apartment in York
5 out of 5 average rating, 25 reviews

Lg. Quiet 1BR Apartment Perfect for Professionals

Lg 1 bedroom apartment in a safe neighborhood. Close to York Hospital, WellSpan’s Apple Hill & OSS. Designated parking just steps from the door. Attached to a business with 24/7 security monitoring and maintenance, with separate entrances. Enjoy quiet evenings—no neighbors above or below! Relax on the front porch, admire the hardwood floors, and enjoy the brand-new walk-in shower. Just minutes from restaurants, a grocery store, a gym, and more!

Top Guest favourite
The exterior of a brick townhouse features multiple large windows framed in white, allowing natural light to fill the interior. Ivy climbs one side of the building, while a sign indicating the pen shop hangs nearby. Sidewalk seating is seen adjacent to the entrance.
Apartment in York
4.99 out of 5 average rating, 288 reviews

Experience Historic York in the Pen House Suite

Work, play, or relax in this centrally located 1860's Federal-style townhouse atop a nostalgic pen shop. Located within the Market District, this private 5 room apartment filled with 18th century simplistic charm has all new modern conveniences contrasting with stucco walls, beamed ceilings and random-width plank floors. Local art, York ephemera, maps and photography throughout the space.

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.).

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, 190 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!

Top Guest favourite
An open concept living area is presented, featuring a comfortable brown sofa with cushions and a decorative throw. A coffee table with slender legs is placed in front. A dining table with four chairs and large windows allows natural light, enhancing the space's cozy feel.
Holiday home in Lancaster
4.98 out of 5 average rating, 168 reviews

Sweet Retreat

Take a break and unwind at this peaceful getaway. We are 5 minutes from Millersville, 25 minutes from Sight and Sound and 45 minutes from Hershey Park. Feel free to bring your bikes and your hiking shoes. We are just minutes away from the Enola low grade rail trail.

Popular amenities for Windsor holiday rentals

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