
Holiday houses in Windsor
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Top-rated holiday rentals in Windsor
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The Trolley House / Romantic getaway
Step into history in our 1860-built stone home, where character meets modern comfort. This charming abode exudes timeless appeal, showcasing the craftsmanship of yesteryear alongside contemporary amenities for a perfect blend of old-world charm and convenience. Nestled along the Pequea Creek, outdoor enthusiasts can embark on scenic hikes right from the front door, leading to a picturesque covered bridge. Immerse yourself in the tranquility of this historic gem, where every corner tells a story.

Beautiful Creekside Cabin
This beautiful, restored cabin is a nature lover's Paradise with a babbling brook that offers solace for the body and soul. It is a retreat that will allow you to feel the presence of God as you relax and take deep breaths! Walking & hiking trails nearby connect to the nearby Conestoga Trail system, Susquehanna River, and The Pinnacle. Explore Southern Lancaster County PA where time slows down and Nature beckons you to explore the wonders of the great Outdoors. Enjoy an original Stone gas FRPL

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

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 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.

Creekside Cabin: Sauna | Hot Tub | Fire Pit |Cozy
🏡 Creekside Cabin: A Rustic-Luxury Retreat Along Fishing Creek Tucked into a wooded stretch along Fishing Creek, Creekside Cabin is the kind of place that slows your heartbeat the moment you arrive. Just 45 minutes from Lancaster and York, this beautifully renovated cabin was built for couples and solo travelers who want the charm of the outdoors without giving up the comforts inside. A private sauna, hot tub, a fire pit, spa-style finishes — it's all here. Save it to your wishlist! ❤️

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.

The Inn- Newly Renovated Designer Furnished
Newly renovated home features all of the modern amenities families enjoy. A large island, a dining table 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.

The Barn at Broadleaf Bend
Nestled in Lancaster County stands a magnificent 1750's Amish tobacco barn, thoughtfully transformed into a unique Airbnb experience. This historic structure, once the largest tobacco barn in the area, maintains its authentic charm while offering modern comforts. This extraordinary accommodation offers a rare opportunity to experience Lancaster County's agricultural history while enjoying the perfect base for exploring all the region has to offer.

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!

Overlook on Front-Modern design - panoramic views
Nestled in the Conewago Hills overlooking the Susquehanna River, this custom getaway combines mountain charm with modern design. The large windows frame the peaceful views perfectly while filling the home with natural light. It's a custom built home with unique character, making for the perfect retreat. We created this space as a place to be refreshed and rejuvenated and we hope it is all that, and more!
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Applewood A-Frame Retreat + Hot tub

Hilltop Guesthouse

A-Frame At Oak Hills: Creekside + Hot Tub + Sauna.

Eclectic Artsy Church Loft

The Boxwood Cottage | boutique stay with hot tub

Studio apartment on 2 acres

Modern 1BR Near York - Sleeps 3 - Renovated

Silver Maple Studio
Destinations to explore
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Ocean City Holiday rentals
- Pittsburgh Holiday rentals
- Cleveland Holiday rentals
- Virginia Beach Holiday rentals
- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Mississauga Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Hersheypark
- M&T Bank Stadium
- Longwood Gardens
- Baltimore Convention Center
- Oriole Park at Camden Yards
- Federal Hill Park
- Liberty Mountain Resort
- Johns Hopkins University
- Dutch Wonderland
- Hershey's Chocolate World
- Spooky Nook Sports
- CFG Bank Arena
- Betterton Beach
- University of Delaware
- Roundtop Mountain Resort
- French Creek State Park
- Patterson Park
- Marsh Creek State Park
- Amish Village
- National Aquarium
- Sight & Sound Theatres
- Caledonia State Park
- Shady Maple Smorgasbord
- Baltimore Museum of Art





