Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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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, 258 reviews

The Carriage House- A Non-Toxic, Peaceful Retreat

🏠 🌻Welcome to The Carriage House - a very unique, NON-TOXIC, extra large 1-bedroom suite located above our three-car garage in a stunning rural area with plenty of outdoor space. 🌿Perfectly situated near many popular venues and Lancaster attractions with a quiet, peaceful feel. 🌷☕️ We, the hosts, live in the main house but respect your privacy. ☑️ Whether you're in town for business, vacation, touring the area, or just need a relaxing retreat, we know you’ll enjoy this charming place! ☺️💫🍷

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, 220 reviews

The Roundtop Chalet (romantic couples retreat)

Indulge in a getaway to our charming cabin, the perfect retreat for all your special celebrations - be it anniversaries, birthdays, or simply a much-needed escape from routine. Perfectly designed for romantic getaways, this cabin seamlessly blends rustic charm with modern comforts. Savour the warmth of a cozy fireplace, unwinding in a hot tub,and indulge with unlimited lattes, crafted by our Breville Touch Espresso Machine. Embrace serenity at its finest and make memories that will last forever

Top guest favourite
Three red Adirondack chairs are positioned along a grassy bank, overlooking a calm body of water. The scene is framed by lush green trees, with sunlight filtering through the leaves, creating a serene atmosphere by the water's edge.
Home in Lancaster
4.96 out of 5 average rating, 155 reviews

Dog-friendly Farmhouse w/ Peaceful Waterfall View

Calming sounds of the waterfall and views of Mill Creek nature 7 minutes from Sight & Sound. Located along a convenient and busy road close to all things Lancaster, this home is truly a getaway in the backyard. The inside, furnished by our neighboring Olde Mill House Shoppes has a modern kitchen and amenities boast comfort and convenience. Stairs are a must in this old home, with 2 bedrooms (1 overlooking the falls & one having 2 queen beds) and a full bath are upstairs. Dogs ok with messaging.

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, 382 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 exterior of a charming stone building is depicted, featuring multiple large windows and a welcoming front porch. A red star adorns the facade, enhancing the rustic appeal. Lush green grass surrounds the structure, contributing to the serene countryside atmosphere.
Flat in Lancaster
4.87 out of 5 average rating, 247 reviews

Historic Stone Mill in Lancaster Countryside

This space is the perfect mix of historic charm and modern design in a beautiful country setting 5 minutes from Millersville University. This buildings age dates to the Early 1800's. It was originally a grist mill that used water from the west branch of the Little Conestoga Creek to power a wheel used to grind flour. The mill has now been turned into a wonderfully updated residence with fantastic views on all sides,including one overlooking the creek. Enjoy the large rooms and peaceful grounds.

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, 174 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.

Guest favourite
Two horses are depicted in a grassy field, one being a mature horse grazing and the other a young foal standing nearby. The area is surrounded by trees and a wooden fence, with yellow wildflowers scattered across the ground.
Farm stay in White Hall
4.81 out of 5 average rating, 177 reviews

Working horse farm retreat! Nearby wedding venue!

Wake up to see horses and deer right from the bedroom window! Experience country living on a working horse farm! Our home sits on a property with horses and the sights and sounds of farm life. Guests will enjoy spacious indoor living and abundant outdoor space in a rural setting. Just minutes from I-83, hiking trails and parks! Whether you’re coming to relax on the porch with a morning coffee, visit the horses, or explore nearby parks and trails, you’ll enjoy an authentic country experience!

Guest favourite
An outdoor seating area is presented with two dark wooden adirondack chairs positioned around a stone fire pit. A scenic view of the Susquehanna River and hills is framed by trees, with a soft sunset glow illuminating the sky.
Cottage in Pequea
4.92 out of 5 average rating, 182 reviews

Charming River view cottage

Take it easy at this unique and tranquil getaway. River view cottage is nestled up on a hillside with beautiful views of the Susquehanna river and Pequea creek. Come relax and enjoy the beauty of the outdoors, the magical sunsets with multiple outdoor seating areas, flower gardens and an outdoor fire pit. The cottage is tucked back in on 5 acres allowing for full privacy. The cottage was built in the 1950s and has a unique, charming character for you and your family/friends to enjoy!

Top guest favourite
The exterior view of the log cabin is set amidst a lush, wooded landscape. A stone path leads to the cabin, which features a spacious outdoor deck adorned with plants and seating. The serene ambiance of the surrounding nature invites relaxation.
Place to stay in Airville
4.98 out of 5 average rating, 243 reviews

Waterfront Log Cabin with Hot Tub

Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

Guest favourite
The living area features a light gray sofa and two comfortable chairs, arranged around a wooden entertainment unit with a large flat-screen TV displaying a tranquil nature scene. A decorative plant and artwork enhance the inviting decor.
Flat in York
4.93 out of 5 average rating, 106 reviews

Cozy Studio + EV Charger

This cozy studio apartment is the perfect retreat for a single person or a couple looking for a comfortable and inviting space. With its warm and inviting atmosphere, this apartment offers a peaceful and relaxing environment. The open layout maximizes the use of space, providing a functional living area, a well-equipped kitchen, and a cozy sleeping area. The apartment is tastefully decorated with modern furnishings and includes all the necessary amenities for a comfortable stay.

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, 127 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.

Top guest favourite
A charming 1950s Cape Cod style home is set against a green lawn with well-maintained shrubs. A gravel driveway leads to a side entrance, while trees provide shade in the background. The house features a sloped roof and a welcoming front porch adorned with decorative greenery.
Home in Millersville
4.92 out of 5 average rating, 194 reviews

Cozy Cape Stay Near Millersville University

🏡 Restored 1950s Cape Cod in a quiet neighborhood near Millersville University. This 4-bedroom home features open-concept living, modern amenities, and a cozy patio. Perfect for family trips, girls’ weekends, or couple getaways. Walk to local restaurants or take a short drive to downtown Lancaster for shows, shopping, and rooftop dining.

Popular amenities for Windsor holiday rentals

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