
Holiday houses in Windsor
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Top-rated holiday rentals in Windsor
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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
ValueFamilyBeach

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!
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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!
FamilyLocationBeach

Restored Distillery | Sunroom + Outdoor Sauna
Stay at this historic c. 1755 stone house that was once an operating distillery, now reimagined with stunning design and eco-friendly geothermal power. The showstopper is the dramatic two-story sunroom with stone walls, artwork, and natural light. Enjoy a chef’s kitchen, Peloton bike, and beautifully furnished living spaces. Outdoors, relax in the BRAND NEW top-of-the-line sauna (installed Fall 2025). 15 min to Lancaster, 40 min to Hershey, and easy drives from Baltimore, Philly, DC, and NYC.
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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.
LocationFamilyIndoor spaces

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.
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The River Nook in Lancaster
Our cozy three bedroom, two bathroom riverside cottage comfortably sleeps 6-8 adults, includes a 3 sided fireplace, fully stocked kitchen, and multiple seating areas both indoors and outdoors. Scandinavian, rustic/modern decor includes a hanging rope bed. Outdoor pavilion and spacious backyard in a quiet neighborhood make this the perfect getaway! *5 min to downtown Lancaster *5 min to the Riverdale Manor *10 min to Dutch Wonderland *15 min to Sight & Sound Theater *40 min to Hershey Park
LocationFamilyGetting around

A-Frame At Oak Hills: Creekside + Hot Tub + Sauna.
This one-of-a-kind A-Frame by Zook Cabins, built into the mountainside, is the perfect place to unwind. Relax in your private outdoor SAUNA or soak in the in-ground HOT TUB surrounded by forest views and the sound of the trickling creek! Enjoy peaceful mornings among the treetrops on the deck, then settle inside on the oversized plush couches! With two beautiful king bedrooms you'll have all the comforts you need for a memorable getaway. Book your stay at Oak Hills today- you deserve it!
ValueLocationBarbecue

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.
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The Barn at Broadleaf Bend
Nestled in Lancaster County stands a magnificent 1750's Amish tobacco barn, thoughtfully transformed its ground floor 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.
ValueFamilyCleanliness

E Maple-The Pleasant Home / Comfort & Ease
Welcome to our home in the heart of Dallastown. A few mins walk to the town main street there are Krua Thai Cafe. Common Grounds Coffee House. Roma’s Pizza Restaurants. A short drive to great breakfast at Tapenade Bistro. Steak house at The Great American Saloon. Close convenient stores like Weis market and Giant. Whether you’re looking for a long term stay or need a quick stop for your journey our space is thoughtfully curated with comfort and ease in mind.
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Oak Haven Estate:Pool+Hot Tub+Pond+Game Room
With beds for 26 GUESTS Oak Haven Estate is perfect for extended families and group retreats and offers space, comfort, and fun for all ages!! This newly renovated home features 7 bedrooms, a GAME ROOM, kids playroom, and multiple gathering spaces. Outside enjoy the POOL, HOT TUB, and large yard. With a fully equipped kitchen, dining areas, and plenty of room to spread out, it’s the ideal place for your large group to stay together and make memories!!
ValueFamilyAccess
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Secluded Log Home, SLPS 10, Pickleball, Fire Pit
LocationFamilyOutdoor spaces

Overlook on Front-Modern design - panoramic views
LocationFamilyComfort

Legacy Lane Retreat - Tennis, Pickleball & Pond!
FamilyLocationBarbecue

Silver Maple Studio
LocationFamilyCleanliness

The York Schoolhouse - Hot Tub - Game Room
FamilyCleanlinessHot tub

Hilltop Guesthouse
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The Boxwood Cottage | boutique stay with hot tub
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Pre-Civil War Farmhouse / Personal Golf Course
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Destinations to explore
- New York 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
- Liberty Mountain Resort
- Johns Hopkins University
- Oriole Park at Camden Yards
- Federal Hill Park
- Dutch Wonderland
- Hershey's Chocolate World
- Betterton Beach
- CFG Bank Arena
- Baltimore Convention Center
- Amish Village
- University of Delaware
- French Creek State Park
- Spooky Nook Sports
- Roundtop Mountain Resort
- Patterson Park
- Marsh Creek State Park
- National Aquarium
- Sight & Sound Theatres
- Harbor East
- Elk Neck State Park
- Caledonia State Park





