
Vacation rentals in Windsor
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Top-rated vacation 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

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!

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!

Luxury Farm Cottage - hot tub & patio
Welcome to the Inglewood Farm! Inspired by Old European design and the Cotswolds of England, this gives you a luxury farm stay in a sweet 2-bedroom cottage. Tucked in a peaceful wooded corner on our 20-acre 1700’s farmstead, you can visit the animals, see the rhythm of our family farm life, and enjoy being in nature. New - Hot tub 2025! Located 3 miles south of Lancaster, we are 15-20 minutes within major attractions including Sight & Sound Theatre, Amish Country, Strasburg, and Lititz.

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.

1700’s historic waterfront cottage
Be a part of history while staying on this waterfront property of the Ironmaster's Mansion. The two-story stone guesthouse, steps away from the mansion, was built in the year 1715. The timeless character of the home, paired with the peaceful property creates an escape that feels like you've gone back in time, all while being only 20 minutes outside of Lancaster City. The mansion was home to the first treasurer of the US, General Edward Hand’s daughter, and President Buchanan’s fiance.

Waterfront Terrain- Relax, Unplug, Enjoy!
RELAX and UNPLUG in the countryside of Lancaster County at this 2,000 sq. ft. house perfect for families, friends groups, and Bridal Party!This cabin is nestled between two hills, making it the most serene spot in the area. You will enjoy hearing the gentle rustles of the creek or spot a deer, or eagle! Play ping-pong or corn hole, in basement or lounge in open concept living room with your favorite beverage. Make the best memories when you choose to stay at the Waterfront Terrain!

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!

Sunrise on Wilson
Welcome! Enjoy a cup of Lancaster County coffee on the back porch and watch the sun rise over the pastures. Our quiet location is ideal for those who wish to relax and unwind. Great for families or those traveling for business alike! We are conveniently and centrally located between York (9 mi.) Lancaster (20 mi.), Hershey (30 mi.), Gettysburg (40 mi.) and Baltimore(60 mi.).
Popular amenities for Windsor vacation rentals
Other great vacation rentals in Windsor

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

E Maple-The Pleasant Home / Comfort & Ease

Morning Glory Inn - Farmhouse

Hilltop Guesthouse

Silver Maple Studio

The Hideaway: hot-tub+Fire-pit+E-Bikes+Secluded

Studio apartment on 2 acres

Log Cabin Beauty - Amish Country - Close to River
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- Hersheypark
- M&T Bank Stadium
- Longwood Gardens
- Baltimore Convention Center
- Johns Hopkins University
- Oriole Park at Camden Yards
- Liberty Mountain Resort
- Federal Hill Park
- Dutch Wonderland
- Hershey's Chocolate World
- CFG Bank Arena
- Betterton Beach
- Spooky Nook Sports
- Amish Village
- University of Delaware
- French Creek State Park
- Roundtop Mountain Resort
- Marsh Creek State Park
- Patterson Park
- National Aquarium
- Sight & Sound Theatres
- Shady Maple Smorgasbord
- Harbor East
- Caledonia State Park





