Holiday rentals 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.
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 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!

Top guest favourite
A cozy bedroom features a spacious bed covered with a light blue quilt. A decorative windmill hangs on an accent wall of rustic bricks. Natural light filters in from a nearby window, and a wooden dresser complements the warm tones of the room.
Farm stay in Mount Joy
4.96 out of 5 average rating, 313 reviews

Historic Farm Suite-2 min to Spooky Nook!

Enjoy this cozy 2nd floor guest suite for 2 in a 200 year old farmhouse! The space is a 3 room guest suite, with private entrance, full bath, bedroom and living room. The listing is NOT for the entire house. Our family is in the process of moving out of the main part of the house. Enjoy petting our goats and watching our cattle. An abundance of various birds, deer, and foxes roam the farm and surrounding area. Spend the evening by the fire pit so you can appreciate the quiet & stars.

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, 550 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 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, 116 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
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
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.

Popular amenities for Windsor holiday rentals

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