Vacation rentals in Windsor

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Cabin in Wrightsville
4.98 out of 5 average rating, 248 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 favorite
The cabin's exterior features a rustic stone chimney and a front porch with a single black chair. Lush greenery surrounds the cabin, enhancing its natural setting. The building is designed with earthy tones, and multiple windows allow light to illuminate the inviting space within.
Cabin in Holtwood
4.92 out of 5 average rating, 261 reviews

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

Top guest favorite
Home in Pequea
4.98 out of 5 average rating, 184 reviews

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.

Top guest favorite
A warm living room is highlighted by wooden beams overhead and natural light streaming through French doors. A cozy sofa is positioned beside a rustic coffee table adorned with decorative items. Soft greenery is placed on surfaces, enhancing a serene environment.
Cabin in Railroad
5.0 out of 5 average rating, 131 reviews

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!

Top guest favorite
A circular gathering area is positioned on a gravel surface, featuring four wooden Adirondack chairs arranged around a stone fire pit. Lush green grass surrounds the space, with trees and a building visible in the background under a partly cloudy sky.
Home in York
4.94 out of 5 average rating, 111 reviews

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!

Top guest favorite
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, 188 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.

Top guest favorite
Home in Airville
5.0 out of 5 average rating, 51 reviews

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!

Top guest favorite
A historic stone exterior is showcased, featuring a dark green door adorned with a circular wreath. Two rectangular windows with individual panes complement the textured stone walls. Planters with greenery are seen beneath the windows, adding a touch of nature to the entrance.
Home in Pequea
4.97 out of 5 average rating, 117 reviews

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.

Top guest favorite
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, 277 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.

Top guest favorite
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, 409 reviews

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.

Top guest favorite
The exterior of a transformed tobacco barn is depicted, featuring a blend of red siding and a stone foundation. Lush landscaping with greenery and decorative features can be seen in front of the structure, which is framed by a clear blue sky.
Barn in Columbia
4.98 out of 5 average rating, 112 reviews

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.

Top guest favorite
The unique exterior of the Shoe House is prominently displayed, featuring a smooth, white plaster finish contrasted by gray accents. A bright yellow door serves as an inviting entrance, framed by small windows. Lush landscaping and a well-maintained yard contribute to the charm of this landmark.
Place to stay in Yorkana
4.93 out of 5 average rating, 170 reviews

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 vacation rentals