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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Windsor vacation rentals

Family House | Living area | 50-inch Smart TV with digital channels, Netflix, DVD player

1. Cozy Cape Cod Bungalow

Cozy Cape Cod Bungalow
3.5 star property
York
10.0 out of 10, Exceptional, (4 reviews)
"Cozy cottage vibe. Well stocked kitchen. "
United States
erica h
$293 nightly
The price is $325
Sep 20 - Sep 21
Total with taxes and fees
Cozy Cape Cod Bungalow
Exterior

2. 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, (150 reviews)
"Fun house to stay in. Despite uniqueness of home, it has everything you need for a comfortable stay. We enjoyed the hot tub in the evening and a couple trip to York for good food."
United States
Abigail H.
$378 nightly
The price is $417
Sep 13 - Sep 14
Total with taxes and fees
Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
TV, fireplace, DVD player, stereo

3. Cozy Cape Cod Bungalow Kg Qn WD Full Kitchen Wifi Desk

Cozy Cape Cod Bungalow Kg Qn WD Full Kitchen Wifi Desk
York
7.4 out of 10, Good, (9 reviews)
"Worked out great, thanks for being available on short notice"
United States
Jeremy M.
$215 nightly
The price is $226
Sep 20 - Sep 21
Total with taxes and fees
Cozy Cape Cod Bungalow Kg Qn WD Full Kitchen Wifi Desk
Smart TV

4. Close to Wellspan, York College, Appell! Washer/dryer in unit.

Close to Wellspan, York College, Appell! Washer/dryer in unit.
York
10.0 out of 10, Exceptional, (2 reviews)
"We had an amazing stay "
United States
Eugene-Marinel B.
$257 nightly
The price is $284
Sep 16 - Sep 17
Total with taxes and fees
Close to Wellspan, York College, Appell! Washer/dryer in unit.
Interior

5. 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, (41 reviews)
"The property was clean the communication with the owner was very clear for parking and how to access the property, and everything was in working order."
United States
Craig
$124 nightly
The price is $137
Sep 14 - Sep 15
Total with taxes and fees
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
Exterior

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

Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
Mountville
10.0 out of 10, Exceptional, (42 reviews)
"Great house in a great location"
United States
Kate H.
$364 nightly
The price is $401
Sep 13 - Sep 14
Total with taxes and fees
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
Exterior

7. 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)
"Everything was clean and as described. Great location, and easy check in/out."
United States
Joseph S.
$289 nightly
The price is $319
Sep 15 - Sep 16
Total with taxes and fees
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
Outdoor pool

8. 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
Sep 13 - Sep 14
Total with taxes and fees
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
Interior

9. The Loft at Riverside

The Loft at Riverside
Lancaster
9.4 out of 10, Exceptional, (63 reviews)
"We stayed for 2 nights and all the amenities were wonderful - clean, comfortable, and gave us easy access to all the sites in Lancaster."
United States
Deborah R.
$194 nightly
The price is $214
Sep 13 - Sep 14
Total with taxes and fees
The Loft at Riverside
Comfort House | Living area

10. 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
$447 nightly
The price is $496
Oct 6 - Oct 7
Total with taxes and fees
The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
Smart TV, DVD player, books, video library

11. "City Hideaway: Off-Grid Luxe"

"City Hideaway: Off-Grid Luxe"
Cabbage Hill
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful and cozy tiny house, helpful and accommodating host. "
United States
Sarah B.
$162 nightly
The price is $179
Sep 13 - Sep 14
Total with taxes and fees
"City Hideaway: Off-Grid Luxe"
Smart TV, fireplace, books

12. 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, (62 reviews)
"Wonderful stay in Lancaster. Very comfortable accommodations and fantastic host."
United States
Jeremy L.
$199 nightly
The price is $220
Sep 22 - Sep 23
Total with taxes and fees
1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly
Outdoor dining

13. Escape to Horse Ranch close to Hershey, Lanc, Nook, Sight & Sound, Amish Country

Escape to Horse Ranch close to Hershey, Lanc, Nook, Sight & Sound, Amish Country
Columbia
10.0 out of 10, Exceptional, (12 reviews)
"Val was a great host and constantly checked in to make sure we had everything we needed. The property is beautiful and very relaxing. We wish we could have stayed longer to interact with the horses more!"
United States
Dylan D.
$238 nightly
The price is $263
Sep 22 - Sep 23
Total with taxes and fees
Escape to Horse Ranch close to Hershey, Lanc, Nook, Sight & Sound, Amish Country
Exterior

14. The Roundtop Chalet romantic couple’s getaway

The Roundtop Chalet romantic couple’s getaway
Wrightsville
9.8 out of 10, Exceptional, (14 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.
$442 nightly
The price is $462
Sep 13 - Sep 14
Total with taxes and fees
The Roundtop Chalet romantic couple’s getaway
TV

15. 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.
$357 nightly
The price is $394
Sep 21 - Sep 22
Total with taxes and fees
The Conservatory-20 min to Lanc!
Interior

16. 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.
$362 nightly
The price is $383
Oct 6 - Oct 7
Total with taxes and fees
Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
TV, fireplace

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

Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom
Columbia
9.6 out of 10, Exceptional, (15 reviews)
"We loved staying here. Perfect for what our family needed."
United States
Debbie E.
$408 nightly
The price is $429
Sep 15 - Sep 16
Total with taxes and fees
Farmhouse|HOT TUB|Fireplace|King Bed|4 Bedroom
Interior

18. Quaint -2-bedroom house in Lancaster with cool AC breeze

Quaint -2-bedroom house in Lancaster with cool AC breeze
Prospect Heights
8.0 out of 10, Very Good, (11 reviews)
"Very clean….convenient location "
United States
Paris
$153 nightly
The price is $169
Sep 29 - Sep 30
Total with taxes and fees
Quaint -2-bedroom house in Lancaster with cool AC breeze
Exterior

19. The Quiet House on Main Street minutes from Everywhere

The Quiet House on Main Street minutes from Everywhere
Shrewsbury
10.0 out of 10, Exceptional, (11 reviews)
"Owner was excellent"
United States
Clint R.
$286 nightly
The price is $315
Sep 21 - Sep 22
Total with taxes and fees
The Quiet House on Main Street minutes from Everywhere
Interior

20. The Pop Loft | Downtown Lancaster

The Pop Loft | Downtown Lancaster
West End
$244 nightly
The price is $270
Sep 14 - Sep 15
Total with taxes and fees
The Pop Loft | Downtown Lancaster
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

Wyndham Garden York

Wyndham Garden York

8/10 Good
"Great value for money"
Kevin 1-night trip
Posted 14 hours ago
Wyndham Garden York

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 $169 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.