Holiday Rentals in Windsor

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Our top choices for Windsor holiday rentals

15 Minutes To Sight & Sound Near Downtown Lancaster w/ Firepit

15 Minutes To Sight & Sound Near Downtown Lancaster w/ Firepit
Lancaster
9.4 out of 10, Exceptional, (8 reviews)
"Lovely, clean, and comfortable accommodations!Perfect location, would definitely stay here again!"
United States
Diane C.
The price is €116
includes taxes & fees
1 Feb - 2 Feb
15 Minutes To Sight & Sound Near Downtown Lancaster w/ Firepit

Lancaster Carriage House w/ Fireplace & Jacuzzi

Lancaster Carriage House w/ Fireplace & Jacuzzi
Lancaster
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Cute property!"
United States
Becky R.
The price is €135
includes taxes & fees
26 Jan - 27 Jan
Lancaster Carriage House w/ Fireplace & Jacuzzi

The Loft at Riverside

The Loft at Riverside
Lancaster
9.4 out of 10, Exceptional, (45 reviews)
"Nice location for visit the Lancaster area!"
United States
Bill S.
The price is €124
includes taxes & fees
25 Jan - 26 Jan
The Loft at Riverside

A Cozy Getaway 5 min from the heart of Lancaster!

A Cozy Getaway 5 min from the heart of Lancaster!
Lancaster
9.2 out of 10, Wonderful, (11 reviews)
"The house was perfect, they’ve made every convenience available for a smooth stay. "
United States
O'Delle H.
The price is €170
includes taxes & fees
25 Jan - 26 Jan
A Cozy Getaway 5 min from the heart of Lancaster!

Lovely Downtown Townhome

Lovely Downtown Townhome
Ross
8.8 out of 10, Excellent, (109 reviews)
"A great spot to stay in Lancaster Center of services and spacious "
United States
Frank D.
The price is €145
includes taxes & fees
26 Jan - 27 Jan
Lovely Downtown Townhome

Modern Farmhouse Getaway I 2 BR, Sleeps up to 6

Modern Farmhouse Getaway I 2 BR, Sleeps up to 6
Elizabethtown
10.0 out of 10, Exceptional, (72 reviews)
"Everything was wonderful, from the location to the house!"
United States
Amelia F.
The price is €244
includes taxes & fees
26 Jan - 27 Jan
Modern Farmhouse Getaway I 2 BR, Sleeps up to 6

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
Lancaster
9.8 out of 10, Exceptional, (36 reviews)
"Excelente"
Mexico
Jairo
The price is €219
includes taxes & fees
25 Jan - 26 Jan
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

Cozy Cape Cod Bungalow

Cozy Cape Cod Bungalow
3.5 star property
York
10.0 out of 10, Exceptional, (2 reviews)
"I have been looking at this property for a few years, wanting a place with a full kitchen and a private house. I gave 5 stars because it was pretty much what I was looking for. The plastic covering on the beds was a bit uncomfortable. I realize it’s more sanitary although I would suggest a washable fitted cover over the plastic mattress pad and then the sheets. It would cut the extra sweating that occurs lying on a sheet over the plastic. Also there was only one extremely worn out dish...
United States
Judith
Cozy Cape Cod Bungalow

Located right at the center of Elizabethtown , Lancaster, York and Hershey park.

Located right at the center of Elizabethtown , Lancaster, York and Hershey park.
Elizabethtown
9.8 out of 10, Exceptional, (35 reviews)
"Was a great place to stay very clean and they had so much to offer. "
United States
Mike D.
The price is €242
includes taxes & fees
25 Jan - 26 Jan
Located right at the center of Elizabethtown , Lancaster, York and Hershey park.

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

Unique tiny home experience in a one of a kind tiny home community!
Elizabethtown
9.4 out of 10, Exceptional, (20 reviews)
"Our first impression of the property was WOW! It was very functional and it was great for a short stay. Very quiet and peaceful stay. "
United States
Kristen T.
The price is €137
includes taxes & fees
3 Feb - 4 Feb
Unique tiny home experience in a one of a kind tiny home community!

The Garden House

The Garden House
Chestnut Hill
9.8 out of 10, Exceptional, (9 reviews)
"A cheerful, unique little house in historic district. Sparkling clean, beautifully decorated, everything you need is provided, smooth entry, great host communication. Would stay again in a heartbeat!"
United States
Nancy D.
The price is €264
includes taxes & fees
24 Feb - 25 Feb
The Garden House

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, (34 reviews)
"Comfortable house in a nice neighborhood. Host was great at communicating with us.Lots of little extras like towels, sheets, coffee and shampoo and bodywash. Great place to stay- close to Lancaster but far enough away from the traffic and crowds. Very nice experience. "
United States
Janet S.
The price is €221
includes taxes & fees
28 Jan - 29 Jan
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!

The Church Street Suite - Downtown, Cozy, Parking

The Church Street Suite - Downtown, Cozy, Parking
Churchtowne
8.0 out of 10, Very good, (1 review)
"This was a clean beautiful apartment. Comfortable bed. Quiet. Perfect for our one night getaway . Highly recommend. The host was very responsive."
United States
Ruth C.
The price is €162
includes taxes & fees
25 Jan - 26 Jan
The Church Street Suite - Downtown, Cozy, Parking

Charming 2-bedroom house with WiFi, AC in enjoyable Lancaster

Charming 2-bedroom house with WiFi, AC in enjoyable Lancaster
Prospect Heights
10.0 out of 10, Exceptional, (6 reviews)
"Perfect for a one night stay. "
United States
Micaiah S.
The price is €224
includes taxes & fees
26 Jan - 27 Jan
Charming 2-bedroom house with WiFi, AC in enjoyable Lancaster

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

Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV
Yorkana
10.0 out of 10, Exceptional, (129 reviews)
"Very cute and surprisingly modern inside!"
United States
Deborah A.
The price is €336
includes taxes & fees
4 Feb - 5 Feb
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

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, (41 reviews)
"This has been our 4th stay and as always it was top notch."
United States
Bradley K.
The price is €169
includes taxes & fees
27 Jan - 28 Jan
1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly

2BR Home Near Shopping & Restaurants

2BR Home Near Shopping & Restaurants
3.0 star property
York
The price is €329
includes taxes & fees
25 Jan - 26 Jan
2BR Home Near Shopping & Restaurants

Cozy Lancaster City Townhouse - Walkable to city sites

Cozy Lancaster City Townhouse - Walkable to city sites
West End
9.4 out of 10, Exceptional, (25 reviews)
"Great spot to stay! "
United States
ML M.
The price is €263
includes taxes & fees
25 Jan - 26 Jan
Cozy Lancaster City Townhouse - Walkable to city sites

Pondview Paradise, Cozy home with pool and pond on 8 acres

Pondview Paradise, Cozy home with pool and pond on 8 acres
Elizabethtown
10.0 out of 10, Exceptional, (51 reviews)
"Very nice place to stay "
United States
Joseph H.
The price is €217
includes taxes & fees
26 Jan - 27 Jan
Pondview Paradise, Cozy home with pool and pond on 8 acres

Comfy renovated townhome - heart of Downtown Lancaster

Comfy renovated townhome - heart of Downtown Lancaster
Chestnut Hill
9.8 out of 10, Exceptional, (15 reviews)
"Great little place with some very cool restaurants and ice cream shops nearby. Hosts were very nice and accommodating. "
United States
Anonymous traveller
The price is €239
includes taxes & fees
24 Feb - 25 Feb
Comfy renovated townhome - heart of 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

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €116 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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 holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windsor has to offer?

Log cabin nestled beside Chiques Creek in historic Lancaster County: This holiday home rental outside of Windsor is located in a rural location, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 Rocky Ridge Park. Heritage Hill Golf Course and AvalancheXpress are a couple of places you'll find in the wider area.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family getaway.