Windsor Vacation Rentals

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    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Windsor

Pennsy Ridge Hideaway: Relax in our centrally-located wooded retreat w/ hot tub
Outdoor spa tub

Pennsy Ridge Hideaway: Relax in our centrally-located wooded retreat w/ hot tub

10.0 out of 10, Exceptional, (198)
"Great place to stay"
Pennsy Ridge Hideaway: Relax in our centrally-located wooded retreat w/ hot tub
Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.
Fridge, microwave, oven, stovetop

Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.

9.8 out of 10, Exceptional, (44)
"Beautiful property "
$365 nightly
The price is $403
Sep 8 - Sep 9
Total with taxes and fees
Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.
Lovely Downtown Townhome
Fridge, microwave, oven, stovetop

Lovely Downtown Townhome

8.6 out of 10, Excellent, (90)
"We had a comfortable stay. Parking was the most challenging but it was fine too! "
$188 nightly
The price is $208
Sep 9 - Sep 10
Total with taxes and fees
Lovely Downtown Townhome
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV
Outdoor spa tub

Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

10.0 out of 10, Exceptional, (122)
"This was a great overnight in a cute spot that we have seen along the higheay for years. Glad our fanily was finally able to check it out!"
$370 nightly
The price is $409
Sep 9 - Sep 10
Total with taxes and fees
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
Beach

LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

9.8 out of 10, Exceptional, (245)
"Beautiful, well cared for rental with a spectacular view."
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
Beautiful Boho Villa on Vine in the heart of Lancaster
Exterior detail

Beautiful Boho Villa on Vine in the heart of Lancaster

9.6 out of 10, Exceptional, (38)
"Very clean and updated property, nestled in the heart of downtown with a short walk to great food, drinks and etc."
$302 nightly
The price is $334
Sep 23 - Sep 24
Total with taxes and fees
Beautiful Boho Villa on Vine in the heart of Lancaster
Waters Edge
Fridge, microwave, oven, stovetop

Waters Edge

10.0 out of 10, Exceptional, (133)
"Our stay was cut short but Brian and his wife were amazing host. We will definitely be returning "
Waters Edge
Unique tiny home experience in a one of a kind tiny home community!
Fridge

Unique tiny home experience in a one of a kind tiny home community!

9.4 out of 10, Exceptional, (16)
"It's a cute tiny home. Area is really nice and close to everything."
$149 nightly
The price is $158
Sep 7 - Sep 8
Total with taxes and fees
Unique tiny home experience in a one of a kind tiny home community!
"City Hideaway: Off-Grid Luxe"
Fridge, oven, stovetop, coffee/tea maker

"City Hideaway: Off-Grid Luxe"

2.0 star property
10.0 out of 10, Exceptional, (18)
"Perfect stay for our night in Lancaster. Everything was super clean and the truck was an amazing clever design. "
$162 nightly
The price is $179
Sep 7 - Sep 8
Total with taxes and fees
"City Hideaway: Off-Grid Luxe"
Spacious 5 bedroom home with large deck and hot tub
Dining

Spacious 5 bedroom home with large deck and hot tub

9.6 out of 10, Exceptional, (31)
"Had a great time. Communication with owner was excellent and timely."
Spacious 5 bedroom home with large deck and hot tub
Perfect family getaway with pool and hot tub close to everything!
Outdoor pool, a heated pool

Perfect family getaway with pool and hot tub close to everything!

9.8 out of 10, Exceptional, (82)
"It was close to the Sight & Sound theater and the Country Kettle Kitchen stores. The swimming pool and hot tub were very nice, but it should be noted that they are shared with the family and other guests. "
Perfect family getaway with pool and hot tub close to everything!
The Garden House
Property grounds

The Garden House

10.0 out of 10, Exceptional, (8)
"Lovely, cozy, vibrant home in a great part of the city. Lots of restaurants to walk to. Easy checkin and checkout process. Home had everything you needed."
$302 nightly
The price is $334
Sep 8 - Sep 9
Total with taxes and fees
The Garden House
Log cabin nestled beside Chiques Creek in historic Lancaster County
Exterior

Log cabin nestled beside Chiques Creek in historic Lancaster County

9.4 out of 10, Exceptional, (116)
"We loved our stay in this log cabin. The setting was beautiful, and the spacious cabin was furnished nicely, including with kitchenware. I had a number of questions before arrival, and the host's responses were quick and helpful. We wish we could have stayed longer!"
Log cabin nestled beside Chiques Creek in historic Lancaster County
Highville Hideaway - 2 bed, 1 bath, country views
Fridge, microwave, oven, stovetop

Highville Hideaway - 2 bed, 1 bath, country views

10.0 out of 10, Exceptional, (1)
"Beautiful, serene location. House very well appointed, hosts easy to communicate with. We'd recommend highly. "
Highville Hideaway - 2 bed, 1 bath, country views
Spacious Hilltop Escape with Basketball, Pingpong & Sunset Firepit
Fridge, microwave, oven, stovetop

Spacious Hilltop Escape with Basketball, Pingpong & Sunset Firepit

10.0 out of 10, Exceptional, (71)
"This property is situated on an expanse of farmland with a lot of privacy and open space. The house is very well-maintained, with a lot of carefully nuanced touches that make guests feel welcome. The host is quite helpful and communicative. Thank you!!"
Spacious Hilltop Escape with Basketball, Pingpong & Sunset Firepit
Quiet studio apt w large deck. 15 min to Lanc city, >10 to Spooky Nook Sports
Property grounds

Quiet studio apt w large deck. 15 min to Lanc city, >10 to Spooky Nook Sports

10.0 out of 10, Exceptional, (1)
"Such an adorable place! It feels much more spacious and even cozier than the pictures let on. The host was super accommodating and responsive. Lots of good eating spots very nearby!"
$138 nightly
The price is $152
Sep 7 - Sep 8
Total with taxes and fees
Quiet studio apt w large deck. 15 min to Lanc city, >10 to Spooky Nook Sports
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
Interior

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

2.0 star property
9.6 out of 10, Exceptional, (20)
"Cozy accommodations and quiet but bustling area! Definitely made the trip more enjoyable!! Would definitely stay again next time I’m in the area! "
$137 nightly
The price is $151
Sep 14 - Sep 15
Total with taxes and fees
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
Near York expo center. It’s half a mile walk to the Carlisle ave entrance.
Exterior detail

Near York expo center. It’s half a mile walk to the Carlisle ave entrance.

10.0 out of 10, Exceptional, (4)
"Nice place. Short distance to the York State Fair. "
Near York expo center. It’s half a mile walk to the Carlisle ave entrance.
An adorable tiny home perfect for your tiny getaway!
Exterior

An adorable tiny home perfect for your tiny getaway!

9.6 out of 10, Exceptional, (20)
"We had a lovely stay. We were excited to stay in a tiny house. We were comfortable."
$150 nightly
The price is $159
Sep 7 - Sep 8
Total with taxes and fees
An adorable tiny home perfect for your tiny getaway!
Restful and Quaint Cottage
Outdoor spa tub

Restful and Quaint Cottage

9.8 out of 10, Exceptional, (123)
"Very nice place for an overnight stay. "
$313 nightly
The price is $345
Sep 8 - Sep 9
Total with taxes and fees
Restful and Quaint Cottage
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

Lancaster Arts Hotel

Lancaster Arts Hotel

10/10 Excellent
"It’s a unique property, in a converted historic warehouse, with an art theme. So lots of exposed brick and paintings on the walls and a sketch pad in each room. Super tasteful and fun. Also clean and modern. The rooms are on the smaller side, but totally fine. And it’s not in the cutest area but a quick drive to the central walkable part of Lancaster. Very reasonable prices, so a great choice if you’re someone who appreciates a boutique hotel rather than a generic chain."
Alice 1-night trip
Posted 5 days ago
Lancaster Arts Hotel
Red Carpet Inn

Red Carpet Inn

10/10 Excellent
"The cleaning ones should wait a little longer for the doors not to knock twice and enter because if I'm in the bathroom and I can't open at the moment they should wait a little longer to enter but everything else was super good Thanks"
Jennifer 2-night trip
Posted 3 months ago
Red Carpet Inn

Find out more about Windsor

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 $151 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Corn Cob Acres Field of Fun, or get out into nature at a spot like Rocky Ridge Park. Heritage Hill Golf Course and Moon Dancer Winery 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.