Windsor Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Windsor

Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV!
10.0 out of 10, Exceptional, (75)
"I've been driving by The Shoe for over 40 years and finally took the opportunity to spend a weekend there with life-long friends. It.Was.Fantastic!!!! It's cozy, cool, creative, and full of history! We were thankful for rainy weather because we did not want to leave! Thank you, Thank You, THANK YOU to the owners and host for preserving this iconic York County site and for the perfect place to have a mini-vacay with my girls!"
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV!
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
10.0 out of 10, Exceptional, (199)
"We just loved staying at The Lake House along the Susquehanna River. The house was lovely and the views of the river were just beautiful."
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
Beautiful Mount Joy Cabin w/ Pool + Sauna!
10.0 out of 10, Exceptional, (17)
"Spacious, clean, private, and well laid out. Love it. Will go back in future"
Beautiful Mount Joy Cabin w/ Pool + Sauna!
Lovely Downtown Townhome
8.8 out of 10, Excellent, (54)
"We were happy overall. The house was clean, so that’s what’s most important."
The price is CA $137
CA $268 total
includes taxes & fees
Jul 7 - Jul 8
Lovely Downtown Townhome
5 bd w Hottub -- mins to Hunting Hiking & Fishing
9.6 out of 10, Exceptional, (25)
"Beautiful property and the home was very clean! Hot tub was also very nice."
The price is CA $334
CA $590 total
includes taxes & fees
Jul 8 - Jul 9
5 bd w Hottub -- mins to Hunting Hiking & Fishing
Perfect family getaway with pool and hot tub close to everything!
9.6 out of 10, Exceptional, (44)
"Myself, my wife, and our dog stayed the weekend while I was in town for a seminar and, truthfully, I can't think of a single thing about this property that wasn't wonderful. It's located close to everything in town without being in town itself. It's right off a main road, but the cottage is set back enough so that it is not obtrusive. The cottage had all the amenities that anyone would need and was beautifully decorated and very well stocked with sundries. The property itself was gorgeous. Just...
Perfect family getaway with pool and hot tub close to everything!
River Rock Room at Muse House: Secluded Luxury in horse country.
9.8 out of 10, Exceptional, (219)
"Had everything you might need. Like home."
The price is CA $273
CA $340 total
includes taxes & fees
Jun 18 - Jun 19
River Rock Room at Muse House: Secluded Luxury in horse country.
Meadow View Cottage
9.8 out of 10, Exceptional, (6)
"Everything was good but no tv n no radio lighting wasnt that great evey thing was clean pots and pan were very old parking was good"
Meadow View Cottage
An adorable tiny home perfect for your tiny getaway!
10.0 out of 10, Exceptional, (2)
"If you're wondering if you would like to try life in a Tiny House, this is a place to experience the space. It was a fun overnight for my Wife and me. A nice alternative to a typical hotel room."
The price is CA $143
CA $215 total
includes taxes & fees
Jun 23 - Jun 24
An adorable tiny home perfect for your tiny getaway!
Cute City Home w/ Private Patio! Walkable to Markets, Coffee Shops & more!
9.8 out of 10, Exceptional, (21)
"Great communication with owner and no issues with check in/out. Parking can be tricky as the roads are narrow. The home itself was the perfect size, it was a cute space and it was very clean!"
Cute City Home w/ Private Patio! Walkable to Markets, Coffee Shops & more!
Cozy Wrightsville Cottage w/ Private Hot Tub!
9.8 out of 10, Exceptional, (31)
"We enjoyed this property for a weekend getaway with our pup. The property was clean and had a lovely view of the river."
Cozy Wrightsville Cottage w/ Private Hot Tub!
Farmstay with pool and firepit
10.0 out of 10, Exceptional, (173)
"Wanted to escape everyday work stress and this was perfect. Beautiful farm, quiet and amazing assortment of animals. Peace and quiet we so needed but close to attractions and great restaurants!!! Look forward to going back in the fall."
Farmstay with pool and firepit
Waters Edge
10.0 out of 10, Exceptional, (93)
"Brian’s beautiful property on the water was fantastic! My family and I rented the property for a special family gathering and birthday celebration. The home was spotless, the beds were very comfortable and the amenities were excellent (hot tub, pool, pool table, etc). Brian was very responsive to any questions I had. He is very thoughtful with how he stocks and prepares the property - e.g. pool toys, ice maker, and there were even retractable baby gates in front of the stairwells. This property...
Waters Edge
Beautiful Boho Villa on Vine in the heart of Lancaster
9.4 out of 10, Exceptional, (10)
"The property was beautiful and was very well kept. would recommend this property to anyone in the area or traveling to the Lancaster area. The Owners are very nice as well."
The price is CA $205
CA $405 total
includes taxes & fees
Jun 19 - Jun 20
Beautiful Boho Villa on Vine in the heart of Lancaster
Beautiful Farmhouse close to Lanc, Hershey, Etown!
9.4 out of 10, Exceptional, (13)
"House & grounds are beautiful. They aren’t kidding! Stairs are steep! Very comfortable stay. Could not get response from my notes to owners regarding a few questions, but did receive two informative form emails from them while we were there. Overall, good stay."
The price is CA $652
CA $916 total
includes taxes & fees
Jul 5 - Jul 6
Beautiful Farmhouse close to Lanc, Hershey, Etown!
Log cabin nestled beside Chiques Creek in historic Lancaster County
9.4 out of 10, Exceptional, (84)
"We had a fantastic time. The listing was as described. The host responded quickly to questions."
Log cabin nestled beside Chiques Creek in historic Lancaster County
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
9.6 out of 10, Exceptional, (5)
"Home was quaint and super convenient to everywhere we needed to be. Hosts were super helpful with any needs we asked for!"
The price is CA $158
CA $330 total
includes taxes & fees
Jun 20 - Jun 21
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
Luxury Manor on Mulberry in the heart of Downtown Lanc
9.6 out of 10, Exceptional, (18)
"Our group of 5 had a great weekend! The property location is perfect, the house itself was nice and newly renovated."
The price is CA $273
CA $483 total
includes taxes & fees
Jun 30 - Jul 1
Luxury Manor on Mulberry in the heart of Downtown Lanc
River View Lodge. 2 living quarters in 1, wrap around deck, jacuzzi, fire pits.
9.6 out of 10, Exceptional, (17)
"Beautiful home! I can see where it would be beautiful in the summertime for a large family. The hot tub was a welcome addition to a chilly night. Our stay was short, and we will try to stay longer in the summer months!"
River View Lodge. 2 living quarters in 1, wrap around deck, jacuzzi, fire pits.
250yo Stone House - Room to Run, Stream to Play In
10.0 out of 10, Exceptional, (43)
"We had a great stay here- looks just like the pictures. Lots of space inside the house to spread out, and the kids had a lot of fun in the creek and roaming outside. Would recommend."
250yo Stone House - Room to Run, Stream to Play In
Don't see what you're looking for?
See all available properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Windsor Vacation Rental Travel Info

Other types of properties in Windsor you may be interested in

Days Inn & Suites by Wyndham Lancaster Amish Country
2.5 star property
7.4 out of 10, Good, (1005)
"very good"
The price is CA $104
CA $115 total
includes taxes & fees
Jun 18 - Jun 19
Days Inn & Suites by Wyndham Lancaster Amish Country
Eden Resort and Suites, BW Premier Collection
3.5 star property
9.2 out of 10, Wonderful, (1004)
"Awesome place"
The price is CA $220
CA $244 total
includes taxes & fees
Jun 23 - Jun 24
Eden Resort and Suites, BW Premier Collection
Lancaster Inn and Suites
2.0 star property
8.8 out of 10, Excellent, (1003)
"Clean room with comfortable beds."
The price is CA $121
CA $135 total
includes taxes & fees
Jul 1 - Jul 2
Lancaster Inn and Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we offer vacation rentals near popular points of interest in Windsor, or you can go with a more secluded option if you're looking for relaxation.

What's the top vacation rental that Windsor has to offer?

LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK : This vacation home rental near Windsor is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Field of Screams, or get out into nature at a spot like Susquehannock State Park. Haines Shoe House and Penn State York are a couple of places you'll find in the larger area.

What’s a vacation rental in Windsor like?

Vacation rentals are private properties you can stay in for a long or short time in Windsor. Vacation rentals provide amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip.

Recent reviews of Windsor properties
Expedia verified reviews