Vacation rentals in Windsor

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!

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.

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.

Stay in a Stunning 1876 Mansion - Walk Downtown

Discover one of Columbia's most beautiful historic homes. A restored 1876 mansion blends grand Victorian architecture with modern comfort— soaring 12-foot ceilings, original woodwork, crystal chandeliers, spacious gathering rooms, private courtyard, and space! Walk to antique shops, coffeehouses, breweries, restaurants, the Susquehanna River, and rail trails. While you visit Lancaster County, a wedding, Spooky Nook, or simply gather with family and friends, you'll have an unforgettable stay.

NorthsideInn: near sight and sound & sickmans mill

Relax and unwind at Northside Inn. Located on a 122 acre working farm, it is great for couples, or spacious enough for groups, showers, or have a meeting at our 11.5ft table. This farm marks the highest elevation of tillable farm ground in Lancaster County, allowing you to enjoy all the views! From the wide open fields, to the gorgeous sunsets, then when the sun goes down look to the North and see the lights of Lancaster city. You will definitely see an Amish buggy pass by during your stay.

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.

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!

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 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.

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!!