Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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Guest favourite
A serene bedroom is featured with a spacious bed dressed in a soft green coverlet. Natural light enters through two windows, framed by light-colored blinds. A wooden dresser and a plant add subtle touches, while a patterned area rug complements the hardwood floor.
Home in Conestoga
4.93 out of 5 average rating, 109 reviews

The Safe Harbor Home (Peaceful, Quiet, Nature)

Quiet and calming, this retreat rests at the end of a private road in a historic village, nestled right up against the forest. Under 30 minutes from: -Spooky Nook Sports -Dutch Wonderland -Tanger Outlets -Sight and Sound Theatres -Downtown Lancaster -Central Market -Lauxmont Farms -Fulton Theatre -Strasburg Railroad -Tanglewood Manor Golf Club -Lancaster Convention Center -56 minutes from Hershey Park -10 minutes from the Pequea Boat Launch -11 minutes from Millersville University

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.

Guest favourite
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.
Flat in York
4.84 out of 5 average rating, 225 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.

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, 143 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, 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, 255 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, 244 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, 543 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
4.84 out of 5 average rating, 371 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
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, 302 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.

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.
Flat in York
4.99 out of 5 average rating, 291 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, 185 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.).

Popular amenities for Windsor holiday rentals

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