Holiday Rentals Windsor from £111: Find Short-Term Rentals & Holiday Accommodations

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

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

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Our top choices for Windsor holiday rentals

A living room with a fireplace, wooden beams, a television, and a red sofa.

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

York

"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!"

Larissa D.

includes taxes & fees

8 Nov - 9 Nov

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

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

Yorkana

Janelle C.

includes taxes & fees

9 Nov - 10 Nov

A staircase with a handrail and a door at the bottom.

3. 2-bedroom 2nd Floor apartment in Mount Joy with off street parking

Mount Joy

Angela B.

includes taxes & fees

8 Nov - 9 Nov

A cozy outdoor patio area with wicker furniture, string lights, and a dining table set for a meal.

4. Lancaster County Townhome Near Amish Country

Columbia

David S.

includes taxes & fees

16 Nov - 17 Nov

A Victorian-style house with a wrap-around porch, a turret, and a brick chimney.

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

Mountville

Emmy Lou H.

includes taxes & fees

1 Dec - 2 Dec

A swimming pool with a covered patio area, a two-story house, and a small shed.

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

West Lancaster

Anna

includes taxes & fees

17 Nov - 18 Nov

A kitchen with a black backsplash, white countertops, a black faucet, and a window with greenery above the sink.

7. The Safe Harbor Home | Quiet Retreat, Fire Pit, Nature

Conestoga

George

includes taxes & fees

19 Nov - 20 Nov

A living room with a fireplace, a television mounted on the wall, and a table with decorative items.

8. 1st Floor Apt: Min to Nook, Amish Country, Hershey, Lancaster City: PetFriendly

Lancaster

Jeremy L.

includes taxes & fees

9 Nov - 10 Nov

A spacious living area with a stone fireplace, large windows, and a cozy seating arrangement.

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

Wrightsville

Leslie A.

includes taxes & fees

10 Nov - 11 Nov

The open, bright feel of the main room is an instant charmer!

10. The Pop Loft | Downtown Lancaster

West End

Cydney E.

includes taxes & fees

15 Nov - 16 Nov

A Victorian-style house with a wrap-around porch, brick foundation, and a turret.

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

Mountville

Melissa S.

includes taxes & fees

9 Nov - 10 Nov

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

York

Stephen N.

includes taxes & fees

11 Nov - 12 Nov

A two-story house with a balcony, a front door, and a small porch area.

13. The Quiet House on Main Street minutes from Everywhere

Shrewsbury

Clint R.

includes taxes & fees

10 Nov - 11 Nov

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.

14. The Conservatory-20 min to Lanc!

Mount Joy

John

includes taxes & fees

16 Nov - 17 Nov

A modern interior with a sofa, rug, wooden accents, and a view through a door.

15. "City Hideaway: Off-Grid Luxe"

Cabbage Hill

Kyle M.

includes taxes & fees

11 Nov - 12 Nov

A hallway with a wooden floor, a brick wall, and a staircase leading to another room.

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

Historic Downtown Lancaster

Lori

includes taxes & fees

16 Nov - 17 Nov

A hallway with a wooden floor, a dining area with a table and chairs, and a staircase with floral wallpaper.

17. Comfy renovated townhome - heart of Downtown Lancaster

Chestnut Hill

Ted S.

includes taxes & fees

8 Nov - 9 Nov

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.

18. Getaway on Grant, heart of Downtown with parking

Chestnut Hill

Jennifer M.

includes taxes & fees

16 Nov - 17 Nov

A living room with a coffee bar, a flat-screen TV, and a large window.

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

Prospect Heights

Elaine

includes taxes & fees

9 Nov - 10 Nov

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Find holiday rentals that suit your style

Top Windsor Hotel Reviews

A modern hotel lobby with a central seating area, a reception desk, and artwork on the walls.

Hampton Inn & Suites York South

York

10/10 Excellent

Purleyman

An outdoor patio area with multiple tables and chairs, a covered seating area, and a view of a golf course in the background.

Heritage Hills Golf Resort

York

8/10 Good

Very good reception from Deb who upgraded us and added breakfast to our package. Also agreed a late check out time as we were golfing the next morning. Bar staff were lovely and the G&T and beer were very welcome after a long drive from Virginia . Evening meal was ok, though quite salty and oily ( I had the scallops), and quite costly for the portion size Golf the next morning was excellent , very helpful staff. Course was beautiful, though some of the buggy paths needed repair. Lovely...

Anna

A Holiday Inn Express hotel with a modern facade, a covered entrance, and a well-lit parking area.

Holiday Inn Express Hotel & Suites York NE - Market by IHG

York

10/10 Excellent

Alan

Sleep Inn & Suites of Lancaster County

Mountville

10/10 Excellent

Deborah

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 £111 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?

Quaint -2-bedroom house in Lancaster with cool AC breeze: This holiday home rental outside of 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 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.

Search Holiday Rentals in Windsor

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor holiday rentals

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

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

3. 2-bedroom 2nd Floor apartment in Mount Joy with off street parking

4. Lancaster County Townhome Near Amish Country

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

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

7. The Safe Harbor Home | Quiet Retreat, Fire Pit, Nature

8. 1st Floor Apt: Min to Nook, Amish Country, Hershey, Lancaster City: PetFriendly

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

10. The Pop Loft | Downtown Lancaster

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

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

13. The Quiet House on Main Street minutes from Everywhere

14. The Conservatory-20 min to Lanc!

15. "City Hideaway: Off-Grid Luxe"

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

17. Comfy renovated townhome - heart of Downtown Lancaster

18. Getaway on Grant, heart of Downtown with parking

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

Find holiday rentals that suit your style

Top Windsor Hotel Reviews

Hampton Inn & Suites York South

10/10 Excellent

Find out more about Windsor

Windsor holiday rentals: An excellent choice for every season

How to find incredible deals on Windsor rentals

Frequently Asked Questions

Can I find holiday rentals in Windsor?

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

What’s there to see and do in Windsor?

What’s a holiday rental in Windsor like?