
Holiday rentals in Windsor
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Top-rated holiday rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.

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

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.

Peaceful Farm, Pond + Fire Pit Close to Lancaster
Escape to our charming countryside retreat! Relax by the large koi pond and dock, surrounded by lush greenery and soothing streams. Enjoy catch & release fishing! Explore acres of private land for peaceful walks. Nearby, John Rudy Park offers hiking and horseback riding trails. Only 20 minutes from quaint Lancaster, PA. Easy access to I-83 and Route 30. Enjoy the best of both worlds with tranquility and accessibility to restaurants and shops, only 10 minutes away. Perfect rejuvenating getaway!

The Creek House: Waterfront with Hot Tub & E-bikes
Featured on Magnolia Network’s “In with the Old” Season 1, Ep. 2 (HBO Max), The Creek House is a hidden gem in the heart of Railroad, PA. Nestled between the NCR Rail Trail and two flowing creeks, this location offers both adventure and relaxation at its finest. Explore the over 40 mile bike trail via E-bike, soak in the hot tub while you enjoy sounds of the creek, or ride the train right through the front yard! This idyllic cabin features professionally designed spaces that are sure to please!

Private Home on Rustic Farm
The Loomis House is a cozy loft cabin on private property. Free from the distractions of the outside world, but with all the conveniences of modern life. Deep Run Farm enjoys a quiet setting on the grounds of a colonial-era farm. Some of the original structures on the property date to the 1800s. This perfect rustic setting is conveniently close to shopping and major highways (US 30 and Interstate 83). Come to disconnect and enjoy the wildlife, or just for a quick lay-over in a quiet space.

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.

"ON THE ROCKS CABIN" the perfect getaway for 2!
Cabin is very charming, but rustic. Kitchen has full size frig, microwave, toaster oven, hot plate, toaster+ keurig. Coffee, condiments, soap & shampoo provided. There is a gas grill. Guests provide their qs sheets, towels, campfire wood & drinking water. A variety of dvd’s & games, hot water in & outside shower & tub. Tubes for floating provided, swim your own risk. Fire pit, creek is stocked. Steps to deck overlooking the creek.Trash goes home with guests, smoking on the decks only.

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.

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.

Cozy Cottage •HOT TUB • FIRE PIT• Peaceful Getaway
🌾 Welcome to Your Cozy Farm Retreat A peaceful, private guest cottage located on our small, quiet farm — complete with your own private hot tub, fire pit, and beautiful views. This is the perfect escape to relax, recharge, and enjoy the countryside. Sip coffee overlooking the fields, unwind in the hot tub under the stars, or explore the local farms, breweries, and trails nearby. Perfect for couples or solo travelers seeking a quiet getaway.

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.

Iconic "Shoe House" w/ Hot Tub, Firepit & Arcade!
👞 Welcome To The Haines Shoe House 👞 Featured On HGTV & The Amazing Race, Our Incredibly Unique Airbnb Is Nestled Along The Historic Lincoln Highway and Sits Beside Beautiful Pennsylvania Farm Fields! Recently Designated A Historic Landmark, We've Meticulously Designed The Shoe House For Our Guests To Feature A Wood-Burning Outdoor Firepit, Charcoal Grill, Outdoor Dining, Hot Tub, 300 Game Arcade Machine & Foosball!
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Applewood A-Frame Retreat + Hot tub

Overlook on Front-Modern design - panoramic views

Cozy In-law Suite on Wooded Property

The Pop Loft | Downtown Lancaster

Riverfront Retreat w/ Beach & Boat Access

The Barn at Broadleaf Bend

Studio apartment on 2 acres

River Front w/ dreamy views - Hot Tub
Destinations to explore
- Norfolk Holiday rentals
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- M&T Bank Stadium
- Hersheypark
- Longwood Gardens
- Baltimore Convention Center
- Oriole Park at Camden Yards
- Liberty Mountain Resort
- Dutch Wonderland
- Betterton Beach
- Patterson Park
- Johns Hopkins University
- Marsh Creek State Park
- French Creek State Park
- Roundtop Mountain Resort
- CFG Bank Arena
- Codorus State Park
- Hershey's Chocolate World
- Caledonia State Park
- National Aquarium
- Spooky Nook Sports
- University of Delaware
- Baltimore Museum of Art
- Loyola University Maryland
- Shady Maple Smorgasbord
- Sight & Sound Theatres





