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, 255 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

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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, 138 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!

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Superhost

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

4.92 out of 5 average rating, 113 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!

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Top guest favorite

Home in Columbia

4.96 out of 5 average rating, 125 reviews

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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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, 191 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.

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Superhost

The exterior of a spacious log home is highlighted, featuring a stone facade and a steeply pitched roof. A large deck extends from the upper level, complementing the natural surroundings with a grassy yard leading to a wooded area in the background.

Cabin in Felton

4.94 out of 5 average rating, 54 reviews

Secluded Log Home, SLPS 10, Pickleball, Fire Pit

This quiet, secluded log home is located just a few minutes drive from Red Lion and Shrewsbury. York is within a 30 min drive. Nearby attractions include, The Markets at Shrewsbury, Avalanche Xpress Ski Resort. The home has 4 Bedrooms total (master suite w king bed and attached bath, additional king bedroom, queen bedroom, Bedroom w 2 double beds). Guests will enjoy the fully equipped kitchen with all the essentials for cooking and large dining table. Pickleball Court and Patio and fire pit.

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Top guest favorite

Home in Airville

5.0 out of 5 average rating, 59 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!

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Superhost

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, 418 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.

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Superhost

A charming single-story home is set on a landscaped lot, featuring large front windows with red shutters. The entrance is accessed by steps and a black metal railing. Surrounding greenery enhances the inviting exterior, framed by a sidewalk leading to the street.

Home in Dallastown

4.91 out of 5 average rating, 35 reviews

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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Guest favorite

Home in York

5.0 out of 5 average rating, 17 reviews

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!!

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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, 174 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!

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Guest favorite

Cabin in Wrightsville

4.95 out of 5 average rating, 62 reviews

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!

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