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Windsor Vacation Rentals

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Windsor vacation rentals

A modern kitchen with white cabinets, a black countertop, and a built-in oven.

1. 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, (42 reviews)
"Property was very clean very homey"
United States
Anna
$255 nightly
The price is $281
Nov 1 - Nov 2
Total with taxes and fees
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
A living room with a fireplace, wooden beams, a television, and a red sofa.

2. 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, (10 reviews)
"Beautiful home in a quiet, convenient location. The check in process was easy, parking available in front of the house and the home was well equipped with linens and cook ware. I was a little hesitant considering some of the other reviews complaining about the house being hot but the 2 window units provided was more than enough during a very humid summer weekend. Thank Todd for sharing your home!"
United States
Larissa D.
$237 nightly
The price is $250
Nov 8 - Nov 9
Total with taxes and fees
Cozy Cape Cod Bungalow Kg Qn WD Full Kitchen Wifi Desk
A cozy outdoor patio area with wicker furniture, string lights, and a dining table set for a meal.

3. Lancaster County Townhome Near Amish Country

Lancaster County Townhome Near Amish Country
Columbia
10.0 out of 10, Exceptional, (4 reviews)
"Great place"
United States
David S.
$519 nightly
The price is $573
Nov 15 - Nov 16
Total with taxes and fees
Lancaster County Townhome Near Amish Country
A staircase with a handrail and a door at the bottom.

4. 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, (45 reviews)
"Great space, much more spacious than the photos appear!"
United States
Angela B.
$139 nightly
The price is $153
Nov 1 - Nov 2
Total with taxes and fees
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
A unique, modern building with a curved facade, a central entrance with a staircase, and a small porch area.

5. 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, (154 reviews)
"We had a great time at the Shoe House! It was a fun and unique experience!"
United States
Janelle C.
$398 nightly
The price is $440
Nov 1 - Nov 2
Total with taxes and fees
Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
A Victorian-style house with a wrap-around porch, a turret, and a brick chimney.

6. 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.
$287 nightly
The price is $317
Nov 16 - Nov 17
Total with taxes and fees
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
A living room with a fireplace, a television mounted on the wall, and a table with decorative items.

7. 1st Floor Apt: Min to Nook, Amish Country, Hershey, Lancaster City: PetFriendly

1st Floor Apt: Min to Nook, Amish Country, Hershey, Lancaster City: PetFriendly
Lancaster
10.0 out of 10, Exceptional, (69 reviews)
"Wonderful stay in Lancaster. Very comfortable accommodations and fantastic host."
United States
Jeremy L.
$212 nightly
The price is $234
Nov 8 - Nov 9
Total with taxes and fees
1st Floor Apt: Min to Nook, Amish Country, Hershey, Lancaster City: PetFriendly
A Victorian-style house with a wrap-around porch, brick foundation, and a turret.

8. 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, (45 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.
$383 nightly
The price is $423
Nov 3 - Nov 4
Total with taxes and fees
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
The open, bright feel of the main room is an instant charmer!

9. The Pop Loft | Downtown Lancaster

The Pop Loft | Downtown Lancaster
West End
10.0 out of 10, Exceptional, (1 review)
"Was clean and tidy and was not far from downtown Lancaster. Very cute and had great amenities."
United States
Cydney E.
$237 nightly
The price is $262
Nov 3 - Nov 4
Total with taxes and fees
The Pop Loft | Downtown Lancaster
A modern interior with a sofa, rug, wooden accents, and a view through a door.

10. "City Hideaway: Off-Grid Luxe"

"City Hideaway: Off-Grid Luxe"
Cabbage Hill
10.0 out of 10, Exceptional, (24 reviews)
"Really cute and well done tiny home. We really enjoyed our stay."
United States
Kyle M.
$181 nightly
The price is $200
Nov 1 - Nov 2
Total with taxes and fees
"City Hideaway: Off-Grid Luxe"
A hallway with wooden floors, a floral rug, a chair, a radiator, and a door with blinds.

11. 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
Oct 31 - Nov 1
Total with taxes and fees
Victorian Home Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP
A spacious living area with a stone fireplace, large windows, and a cozy seating arrangement.

12. Stone Cottage at Roundtop Estate couples Retreat with hot tub

Stone Cottage at Roundtop Estate couples Retreat with hot tub
Wrightsville
10.0 out of 10, Exceptional, (10 reviews)
"A beautiful property and such a relaxing space. Everything was top notch. We hated to leave."
United States
Rebecca H.
$423 nightly
The price is $442
Nov 3 - Nov 4
Total with taxes and fees
Stone Cottage at Roundtop Estate couples Retreat with hot tub
A modern kitchen with white cabinetry, a black countertop, and a wooden floor. There is a refrigerator on the right and a sink on the left.

13. Getaway on Grant, heart of Downtown with parking

Getaway on Grant, heart of Downtown with parking
Chestnut Hill
9.8 out of 10, Exceptional, (51 reviews)
"Terrific accommodations within walking distance to some shops and restaurants! Will definitely stay at this location again! "
United States
Jennifer M.
$317 nightly
The price is $350
Nov 2 - Nov 3
Total with taxes and fees
Getaway on Grant, heart of Downtown with parking
A hallway with a wooden floor, a brick wall, and a staircase leading to another room.

14. Beautiful Boho Villa on Vine in the heart of Lancaster

Beautiful Boho Villa on Vine in the heart of Lancaster
Historic Downtown Lancaster
9.4 out of 10, Exceptional, (59 reviews)
"This was a beautiful rental that was exactly as described. The communication was fantastic and the location was perfect."
United States
Lori
$336 nightly
The price is $370
Nov 16 - Nov 17
Total with taxes and fees
Beautiful Boho Villa on Vine in the heart of Lancaster
A two-story wooden cabin with a balcony, surrounded by a well-maintained garden and trees.

15. The River Shack *kayaks*hottub*fishing*quiet*family

The River Shack *kayaks*hottub*fishing*quiet*family
Airville
9.8 out of 10, Exceptional, (13 reviews)
"This property was great, everything you could need was provided. We really enjoyed our stay"
United States
Barb R.
$393 nightly
The price is $434
Nov 2 - Nov 3
Total with taxes and fees
The River Shack *kayaks*hottub*fishing*quiet*family
A hallway with a wooden floor, a dining area with a table and chairs, and a staircase with floral wallpaper.

16. Comfy renovated townhome - heart of Downtown Lancaster

Comfy renovated townhome - heart of Downtown Lancaster
Chestnut Hill
10.0 out of 10, Exceptional, (21 reviews)
"Enjoyed our stay, plenty to do in the neighborhood and walkable to downtown."
United States
Ted S.
$320 nightly
The price is $353
Nov 2 - Nov 3
Total with taxes and fees
Comfy renovated townhome - heart of Downtown Lancaster
A two-story house with a balcony, a front door, and a small porch area.

17. 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, (16 reviews)
"Owner was excellent"
United States
Clint R.
$291 nightly
The price is $321
Nov 4 - Nov 5
Total with taxes and fees
The Quiet House on Main Street minutes from Everywhere
A living room with wicker furniture, a round coffee table, and a hanging light fixture.

18. Quaint 2 BDRM With Fenced in Backyard

Quaint 2 BDRM With Fenced in Backyard
Chestnut Hill
9.4 out of 10, Exceptional, (6 reviews)
"Easy access to downtown Lancaster."
United States
Debbie
$384 nightly
The price is $400
Nov 9 - Nov 10
Total with taxes and fees
Quaint 2 BDRM With Fenced in Backyard
A bedroom with a bed, a TV, a radiator, two windows with blinds, and a hanging light fixture.

19. The Churchtowne Hideaway | Downtown | Central

The Churchtowne Hideaway | Downtown | Central
Churchtowne
8.0 out of 10, Very good, (8 reviews)
"Beautiful, spotless apartment in a great location! Easy walk to the Central Market and so many great eating spots. "
United States
Theresa B.
$181 nightly
The price is $200
Nov 2 - Nov 3
Total with taxes and fees
The Churchtowne Hideaway | Downtown | Central
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.

20. The Conservatory-20 min to Lanc!

The Conservatory-20 min to Lanc!
Mount Joy
9.6 out of 10, Exceptional, (47 reviews)
"The property was exactly as described which is always a plus in our book. An eclectic home that was a lot of fun to explore. Well decorated but whimsically, not predictable. Where modernization was essential (kitchen and bathrooms) it was exquisite. We absolutely enjoyed our stay there and would book it again."
United States
John
$365 nightly
The price is $403
Nov 9 - Nov 10
Total with taxes and fees
The Conservatory-20 min to Lanc!
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

Inn at York

Inn at York

10/10 Excellent
"Give a Thums up"
Brandie 2-night trip
Posted 14 hours ago
Inn at 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 $153 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.