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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Windsor vacation rentals

A unique, modern building with a curved facade, a central entrance with a staircase, and a small porch area.

1. Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!

Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
Yorkana
10.0 out of 10, Exceptional, (152 reviews)
"We had a great time at the Shoe House! It was a fun and unique experience!"
United States
Janelle C.
$433 nightly
The price is $478
Oct 5 - Oct 6
Total with taxes and fees
Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
A cabin with a deck, surrounded by trees and a small stream.

2. The Roundtop Chalet romantic couple’s getaway

The Roundtop Chalet romantic couple’s getaway
Wrightsville
9.8 out of 10, Exceptional, (15 reviews)
"Our stay the Roundtop Chalet was a wonderful retreat. We had stunning views of the snowfall and enjoyed delicious espresso & waffles. The recommend the comfortable bed and the hot tub. "
United States
Amy S.
The Roundtop Chalet romantic couple’s getaway
A Victorian-style house with a wrap-around porch, a turret, and a brick chimney.

3. Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!

Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
Mountville
9.8 out of 10, Exceptional, (43 reviews)
"Perfect for the six of us visiting family in the area. The kitchen amenities we needed for breakfast, comfy beds, and a clean house."
United States
Emmy Lou H.
$269 nightly
The price is $297
Oct 5 - Oct 6
Total with taxes and fees
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
A swimming pool with a covered patio area, a two-story house, and a small shed.

4. Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
West Lancaster
9.4 out of 10, Exceptional, (41 reviews)
"Property was very clean very homey"
United States
Anna
$255 nightly
The price is $281
Oct 5 - Oct 6
Total with taxes and fees
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
A cozy outdoor patio area with wicker furniture, string lights, and a dining table set for a meal.

5. Lancaster County Townhome Near Amish Country

Lancaster County Townhome Near Amish Country
Columbia
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful stay! Cute, clean, and well stacked. Great communication with host!!"
United States
Shannon S.
$486 nightly
The price is $537
Oct 14 - Oct 15
Total with taxes and fees
Lancaster County Townhome Near Amish Country
A bedroom with a bed, bedside tables, a lamp, a TV, and a window with curtains.

6. Work & Play! Home 1 Mi to Dtwn & Central Market

Work & Play! Home 1 Mi to Dtwn & Central Market
3.0 star property
York
$351 nightly
The price is $389
Oct 26 - Oct 27
Total with taxes and fees
Work & Play! Home 1 Mi to Dtwn & Central Market
A living room with a television, a sofa, a chair, and a patterned rug.

7. The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP

The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
3.5 star property
York
$422 nightly
The price is $468
Nov 2 - Nov 3
Total with taxes and fees
The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
A white house with a garage, a staircase leading to a porch, a chair, a small table, and two bicycles.

8. THE RIVERFRONT BOATHOUSE

THE RIVERFRONT BOATHOUSE
York
10.0 out of 10, Exceptional, (11 reviews)
"The house was very clean and well appointed."
United States
Amanda M.
$404 nightly
The price is $419
Oct 14 - Oct 15
Total with taxes and fees
THE RIVERFRONT BOATHOUSE
An outdoor patio area with string lights, seating, and planters.

9. Historic York Schoolhouse Retreat | Hot Tub • Game Room • Fire Pit • Sleeps 9

Historic York Schoolhouse Retreat | Hot Tub • Game Room • Fire Pit • Sleeps 9
York
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great. Enjoyed the outdoor area. Hot tub was clean. Coffee bar was well stocked with coffee. We appreciated that."
United States
Adam B.
$439 nightly
The price is $485
Oct 5 - Oct 6
Total with taxes and fees
Historic York Schoolhouse Retreat | Hot Tub • Game Room • Fire Pit • Sleeps 9
A Victorian-style house with a wrap-around porch, brick foundation, and a turret.

10. Victorian Manor on Main w/ 6 beds-10 mins to Lanc!

Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
Mountville
9.8 out of 10, Exceptional, (44 reviews)
"We had a lovely stay for our gaming weekend. The check in process was easy and we enjoyed being within walking distance of a restaurant."
United States
Melissa S.
$364 nightly
The price is $401
Oct 12 - Oct 13
Total with taxes and fees
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
A staircase with a handrail and a door at the bottom.

11. 2-bedroom 2nd Floor apartment in Mount Joy with off street parking

2-bedroom 2nd Floor apartment in Mount Joy with off street parking
Mount Joy
9.8 out of 10, Exceptional, (43 reviews)
"Great space, much more spacious than the photos appear!"
United States
Angela B.
$142 nightly
The price is $157
Oct 5 - Oct 6
Total with taxes and fees
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
A hallway with wooden floors, a floral rug, a chair, a radiator, and a door with blinds.

12. Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP

Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
York
4.6 out of 10, (8 reviews)
"The house itself has beautiful antique features, particularly the wooden entryway. Despite the unusual cold snap, the radiators kept us very warm."
United States
Stephen N.
$339 nightly
The price is $358
Nov 2 - Nov 3
Total with taxes and fees
Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
A bedroom with a bed, bedside tables, a lamp, a TV, and a window with curtains.

13. Work & Play! Home 1 Mi to Dtwn & Central Market

Work & Play! Home 1 Mi to Dtwn & Central Market
York
7.8 out of 10, Good, (6 reviews)
"The house was clean and very well stocked. Check in/check out process is simple. The owner/manager responded quickly when I had a question. Do not hesitate to book this property."
United States
Christopher A.
$355 nightly
The price is $392
Oct 26 - Oct 27
Total with taxes and fees
Work & Play! Home 1 Mi to Dtwn & Central Market
A two-story house with a balcony, a front door, and a small porch area.

14. The Quiet House on Main Street minutes from Everywhere

The Quiet House on Main Street minutes from Everywhere
Shrewsbury
9.8 out of 10, Exceptional, (13 reviews)
"Owner was excellent"
United States
Clint R.
$291 nightly
The price is $321
Oct 12 - Oct 13
Total with taxes and fees
The Quiet House on Main Street minutes from Everywhere
A living room with a fireplace, sofa, coffee table, and a television mounted on the wall.

15. Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom

Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom
Columbia
9.8 out of 10, Exceptional, (17 reviews)
"We loved staying here. Perfect for what our family needed."
United States
Debbie E.
$471 nightly
The price is $499
Oct 7 - Oct 8
Total with taxes and fees
Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom
A living room with a fireplace, a television mounted on the wall, and a table with decorative items.

16. 1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly

1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly
Lancaster
10.0 out of 10, Exceptional, (66 reviews)
"Wonderful stay in Lancaster. Very comfortable accommodations and fantastic host."
United States
Jeremy L.
$181 nightly
The price is $200
Oct 5 - Oct 6
Total with taxes and fees
1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly
A dining area with a wooden table and chairs, a chandelier, and sheer curtains.

17. 4-bedroom house in amazing Lancaster County in quaint village of Conestoga.

4-bedroom house in amazing Lancaster County in quaint village of Conestoga.
Conestoga
8.6 out of 10, Excellent, (7 reviews)
"Great place to stay for our family!"
United States
Joseph F.
$320 nightly
The price is $353
Oct 5 - Oct 6
Total with taxes and fees
4-bedroom house in amazing Lancaster County in quaint village of Conestoga.
A living room with a teal sofa, a brown ottoman, and a wooden coffee table. There is a dining area with a table and chairs.

18. The Conservatory-20 min to Lanc!

The Conservatory-20 min to Lanc!
Mount Joy
9.6 out of 10, Exceptional, (46 reviews)
"The house was as advertised. Very clean and easy check in process. Close and easy drive to Spooky Nook Sports."
United States
Julie L.
$344 nightly
The price is $380
Nov 3 - Nov 4
Total with taxes and fees
The Conservatory-20 min to Lanc!
A spacious bedroom with a four-poster bed, a sitting area with a chair and a small table, and large windows with blinds.

19. River Rock Room at Muse House: Secluded Luxury in horse country.

River Rock Room at Muse House: Secluded Luxury in horse country.
Willow Street
9.8 out of 10, Exceptional, (304 reviews)
"The property was amazing! The host was outstanding in helping us and communicating. I would highly recommend this property as a great escape and a very peaceful place to stay."
United States
Chad C.
$256 nightly
The price is $283
Oct 6 - Oct 7
Total with taxes and fees
River Rock Room at Muse House: Secluded Luxury in horse country.
A covered deck with a grill and picnic table, a red door, and a view of trees.

20. Enola Trail Getaway *bikes*rural

Enola Trail Getaway *bikes*rural
Pequea
10.0 out of 10, Exceptional, (6 reviews)
"This was a wonderful stay, huge yard, beautiful. Calm and quiet had everything we needed for 3 families "
United States
Ryan B.
$420 nightly
The price is $464
Oct 5 - Oct 6
Total with taxes and fees
Enola Trail Getaway *bikes*rural
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.
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Top Windsor Hotel Reviews

Eden Resort and Suites, BW Premier Collection

Eden Resort and Suites, BW Premier Collection

10/10 Excellent
"Booked this stay for some family members to relax. They enjoyed it as much as I did. Will be returning soon!"
Ternessa 1-night trip
Posted less than an hour ago
Eden Resort and Suites, BW Premier Collection

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $157 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Quaint -2-bedroom house in Lancaster with cool AC breeze: This vacation home rental near Windsor has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Corn Cob Acres Field of Fun, or get out into nature at a spot like Rocky Ridge Park. Heritage Hill Golf Course and Haines Shoe House 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.