Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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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, 377 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.

Top guest favourite
A cabin is nestled among the trees, featuring a mix of wood siding and large windows. A screened-in porch extends from the upper level, while a series of stone steps lead to the entry. Lush greenery and landscaping adorn the surroundings.
Cabin in York Haven
4.95 out of 5 average rating, 148 reviews

Conewago Cabin #1

Here you will find a quiet, simple place to stay with a nice view overlooking the creek. It has all the necessary amenities. Fully stocked kitchen with dishwasher. Full size washer and dryer. There is a small porch overlooking the creek. Sony 50" smart tv Keurig with a complimentary assortment of coffee pods. Fireplace This cabin has its own private fire pit. *Pets are welcome, there is a once per stay $20 pet fee. Two pets maximum please. **No smoking or vaping of any kind is allowed.

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, 170 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, 258 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!

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, 551 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.

Superhost
A spacious bed is positioned in a well-lit room with soft bedding and neutral tones. Textured wall art adds visual interest, while a decorative pennant displays the name 'Lancaster.' A window crafted from glass blocks allows natural light to fill the space.
Flat in Marietta
4.83 out of 5 average rating, 376 reviews

Efficiency apartment in Historic Marietta

This efficiency apartment is part of a 19th century home in historic Marietta, PA. The apartment has it's own private entrance so it is completely separate from our actual house. We are right in the heart of historic Marietta, PA. Enjoy the historic architecture of an old train town and unique and vibrant bars/restaurants that Marietta has to offer. Marietta is located on the Susquehanna river in Lancaster county and is a convenient central location to Lancaster, York and Harrisburg.

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, 116 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 spacious room features a king-sized bed framed by framed photographs. A wooden chair sits beside a small table with a plant. Sliding glass doors open to a private balcony, allowing natural light to fill the space.
Guest suite in Peach Bottom
5 out of 5 average rating, 166 reviews

Conowingo Creek Casual

Kick back and relax in this handicap accessible, clean and stylish country charm efficiency apartment, complete with two outdoor seating spaces, walking paths and beautiful scenery located in rural southern Lancaster County. The area is surrounded by country and Amish charm, with nearby hiking trails, while a 30 minute drive will have you in downtown historic Lancaster City where you can stroll, shop and on Tuesday, Friday and Saturday visit the historic Central Market.

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, 252 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 Lancaster attractions, and has a quiet and peaceful feel. ☕️ 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 retreat. ☺️

Top guest favourite
An open-concept living area features a spacious teal sectional sofa and a rustic coffee table atop a textured area rug. Natural light fills the room through a large window adorned with light curtains, while wooden beams and accents lend warmth to the space.
Barn in Lancaster
4.99 out of 5 average rating, 311 reviews

The Barn on Fox Alley

Welcome to The Barn on Fox Alley—a piece of history nestled in the heart of Lancaster city. The Barn on Fox Alley is a repurposed garage built in 1999, transformed into a magnificent Amish barn that pays homage to Lancaster county’s rich heritage. Step inside, and you'll find yourself immersed in the warmth and character of a bygone era. The spacious interior of the barn is meticulously adorned with hand-hewn reused floors and reclaimed barn wood throughout.

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
4.84 out of 5 average rating, 126 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.

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
4.86 out of 5 average rating, 183 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 with KING bed, full PRIVATE attached 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.

Popular amenities for Windsor holiday rentals

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