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

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!

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.

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.

The River House: Family Friendly

Bring the whole family to this beautiful River House with lots of room for fun + outdoor activities. The home is cozy and warm with view of the river. We've added board games, toys for your littles, and Smart TVs for movie nights. Outside you'll find a hot tub facing the river, a BREEO smoke-less firepit for campfire nights, and a propane grill. Located directly across from the Pequea Boat dock with a boat launch and fishing pier- bring your kayaks, tubes, and fishing lines for endless fun.

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!

Hilltop Manor: Hot tub+ Saltwater & Heated Pool

Prepare to be enchanted by a breathtaking property. Whether you’re seeking solitude or planning a memorable gathering, The Manor caters to every mood. Unwind in pockets of comfort or gather with loved ones in the expansive living room, sunlit patio, pool or hot tub area. Beyond the home, adventure awaits. Enjoy a walk/run along the Enola Low Grade Trail, or explore downtown Lancaster, only a 20 minute drive. Dutch Wonderland, Sight & Sound & the outlets are a 25-30 minute drive.

Stunning Waterfront Views/Spacious Luxury Home

➡️ SLEEPS 19+ ➡️ FULLY FENCED OUTDOOR AREA ➡️ 5 BEDROOMS +Kids room with sleeping area ➡️ 6.5 BATHROOMS ➡️ 10 BEDS ➡️ PRIVATE IN-LAW QUARTERS ➡️ 2 BREVILLE ESPRESSO COFFEE MAKERS ➡️ INFINITI GAME TABLE & ARCADE CAR RACING ➡️ CHRISTMAS TREE (SEASONAL) ➡️ PRIVATE BOAT DOCK This home not only offers water views, it sits directly on the water, offering unmatched views from all living spaces and most of the bedrooms. Paddleboards available. Rent a boat, or bring your own!

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.

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!