Windsor Vacation Rentals from $175: Search Short-Term Rentals

Q: What's the top vacation rental in Windsor?

3 Bed House Sleeps 5 - Parking, Garden, Pets : You might want to consider this vacation home rental near Windsor, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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Our top choices for Windsor vacation rentals

A modern kitchen with a central island, pendant lighting, and a view of the city through large windows.

1. Hampden Apartments - The Louis

Eton

Lucy

$176 nightly

Aug 27 - Aug 28

Total with taxes and fees

A modern living room with a grey sofa, a dining table with chairs, and a large window with shelves.

2. Your Windsor Retreat | 1Bed/1Bath + Free Parking

Windsor City Centre

Toni

$349 nightly

Aug 28 - Aug 29

Total with taxes and fees

A neatly made bed with a grey quilt, a tray with croissants and orange juice, and a window with a view of houses.

3. Hampden Apartments - the Diana

Windsor City Centre

Craig

A cobblestone street with buildings, a sign for 'The Castle Hotel,' and outdoor seating.

4. 1BR|Parking|Doorstep Of Windsor Castle|By Tempstay

Windsor City Centre

Richard J.

$244 nightly

Aug 26 - Aug 27

Total with taxes and fees

A bedroom with a bed, bedside table, lamp, and a towel rack.

5. Spacious Apartment with Private Garden By Tempstay

Windsor City Centre

Sherry N.

$289 nightly

Aug 27 - Aug 28

Total with taxes and fees

A modern kitchen with a central island, two bar stools, a stainless steel range hood, and a window with blinds.

6. Hampden Apartments - The William

Eton

Ian

$147 nightly

Sep 17 - Sep 18

Total with taxes and fees

A modern house with a dark exterior, a patio with outdoor furniture, and a white umbrella.

7. Willow Court Farm

Windsor

Anne

$200 nightly

Sep 6 - Sep 7

Total with taxes and fees

A bedroom with a bed, a desk, a chair, a window, and a balcony.

8. Hampden Apartments - The Edward

Windsor City Centre

david

$156 nightly

Aug 27 - Aug 28

Total with taxes and fees

A modern bedroom with a bed, bedside table, lamp, and a TV.

9. Chic Studio Steps from Windsor Castle

Windsor City Centre

Ogonnaya L.

$206 nightly

Sep 7 - Sep 8

Total with taxes and fees

A modern living room with a flat-screen TV, a sofa, and a coffee table. There is a kitchen area with a dining table and bar stools.

10. Hampden Apartments - The George

Windsor City Centre

Alison

$328 nightly

Aug 30 - Aug 31

Total with taxes and fees

A modern loft apartment with a dining area, kitchen, and living space.

11. Hampden apartments - The Richard

Windsor City Centre

Pamela

$257 nightly

Aug 31 - Sep 1

Total with taxes and fees

A cozy bedroom with a large bed, a grey sofa, a patterned rug, a window with curtains, and a fireplace.

12. Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish

Windsor City Centre

"The house was very clean and a great location! We appreciated the provided fans throughout the house. Bathroom was well kept with shower toiletries available. We had to reach out to the host on the day of check in for access codes. We had to search for the Wifi information when there was no response for days from the host. Parking is not included, but there is a paid lot nearby. Since we stayed during the hot summer, the smells from trash were hard to tolerate. Overall, we would stay here...

Susan

$374 nightly

Aug 25 - Aug 26

Total with taxes and fees

A modern living room with a sofa and armchair, a coffee table, and a kitchen area with cabinets and appliances.

13. Windsor Gem: 1 Bed|1 Bath| Free Parking

Windsor City Centre

Michelle P.

$281 nightly

Sep 8 - Sep 9

Total with taxes and fees

A wooden interior with a kitchen, a chandelier, a TV, and a trash bin.

14. A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

Old Windsor

John W.

$175 nightly

Sep 2 - Sep 3

Total with taxes and fees

A cozy living room with a green sofa, a decorative tapestry, and a high ceiling with exposed beams.

15. Copper Castle & Petting Farm near Legoland

Windsor

HAYLEY

$255 nightly

Sep 6 - Sep 7

Total with taxes and fees

A modern bedroom with a large bed, a desk, and a sliding door leading to a balcony.

16. Central Windsor Gem | 1BR Penthouse + Balcony

Windsor City Centre

Steven K.

$247 nightly

Sep 14 - Sep 15

Total with taxes and fees

A modern kitchen with a central island, recessed lighting, and a view to the outside.

17. Stunning Central Windsor Town House

Windsor City Centre

Lisa

$457 nightly

Aug 30 - Aug 31

Total with taxes and fees

A bedroom with a large bed, two bedside tables, a tray with breakfast, and a view of the sea through the window.

18. Hampden Apartments - The Henry

Windsor City Centre

Jeremy

$230 nightly

Aug 31 - Sep 1

Total with taxes and fees

19. 1BR Gem, Private Parking - VAT Q - By Tempstay

Clewer East

Anne J.

$240 nightly

Aug 25 - Aug 26

Total with taxes and fees

A modern living room with a grey sofa, a glass coffee table with orange juice, and a large window with a view of stone buildings.

20. Central Apartment Facing Windsor Castle

Windsor City Centre

Keith

$257 nightly

Aug 28 - Aug 29

Total with taxes and fees

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Top Windsor Hotel Reviews

Macdonald Windsor Hotel

8/10 Good

"Matthew is, again, a super-helpful member of staff. He's willing to help with luggage, porterage, directions, even sorted out a cafe for us one time. He's just great. The lighting is low and calm, perhaps a little too low at some points, ie the reading lamps. The bathrooms are clean and well-appointed. Mind the edge of the bath, though, the shower water runs all round the edges and onto the floor. We didn't have breakfast, and we didn't use the parking - there doesn't seem to be much parking. We booked with another provider."

Oakley Court

10/10 Excellent

"Oakley Court is a beautiful hotel. The interiors manage to achieve both a sense of opulence and a feeling of being one’s own, at home. The spaces work equally well for a day time hang out but also provide cosy corner and fireplaces to sit alongside in the evening. Staff have a good balance of providing everything you need whilst still offering you privacy. We stayed in a Manor House room which are large on proportion, have a small seating area and lovely views of the gardens and river. We were also lucky enough to stay when the sun was shining and able to loose (willingly) hours to a watching the world go by on the lawn alongside the River. It gives a real sense of peace. The main Oakley Court menu is good but they also host guest chefs. Beyond the hotel there are a number of Michelin and Gastro style pubs that are a short taxi ride away. I’ve listed them on Instagram @takenbytoria It’s a would recommend and would return (hopefully soon)."

Riverside bungalow, Hot Tub/Sauna, Nr Legoland, Windsor, Thorpe Park Theme Park.

10/10 Excellent

"10/10 — we really enjoyed our stay! Everything was perfect and the place had everything we needed. The kitchen was fully equipped, including tea, coffee and all the essentials, and there was even a lovely bottle of champagne waiting for us!It’s a beautiful, private place to stay, relax and switch off. The sauna and jacuzzi were amazing, and the BBQ was all ready to use as well.The hosts were incredibly kind and even offered us an extra day for free, which was such a lovely surprise and really appreciated.Highly recommend this place! We’re already looking forward to visiting again!"

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 $175 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.

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Things to do in Windsor

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we have vacation rentals in Windsor close to LEGOLAND® Windsor, or you can choose a more secluded option if you want a relaxing stay. Visitors like the array of shops and scenic riverfront in Windsor. While you're here, grab a bite or have a drink at the top-notch restaurants and lively bars.

What's the top vacation rental in Windsor?

3 Bed House Sleeps 5 - Parking, Garden, Pets: You might want to consider this vacation home rental near Windsor, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Windsor?

Choose from 37 Expedia vacation rentals in Windsor for a memorable vacation.

What’s there to see and do in Windsor?

LEGOLAND® Windsor and Queen Mary's Dolls' House are a couple of family-friendly sights, whereas cultural attractions include Theatre Royal and Frogmore House. You’ll find favorite places to visit like Wembley Stadium and Warner Bros. Studio Tour London in the larger area.

What’s a vacation rental in Windsor like?

Vacation rentals are privately owned properties where you can stay for short or long periods in Windsor. Vacation rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip.

Room 1

Check prices for these dates

Our top choices for Windsor vacation rentals

1. Hampden Apartments - The Louis

2. Your Windsor Retreat | 1Bed/1Bath + Free Parking

3. Hampden Apartments - the Diana

4. 1BR|Parking|Doorstep Of Windsor Castle|By Tempstay

5. Spacious Apartment with Private Garden By Tempstay

6. Hampden Apartments - The William

7. Willow Court Farm

8. Hampden Apartments - The Edward

9. Chic Studio Steps from Windsor Castle

10. Hampden Apartments - The George

11. Hampden apartments - The Richard

12. Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish

13. Windsor Gem: 1 Bed|1 Bath| Free Parking

14. A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

15. Copper Castle & Petting Farm near Legoland

16. Central Windsor Gem | 1BR Penthouse + Balcony

17. Stunning Central Windsor Town House

18. Hampden Apartments - The Henry

19. 1BR Gem, Private Parking - VAT Q - By Tempstay

20. Central Apartment Facing Windsor Castle

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Macdonald Windsor Hotel

De Vere Beaumont Estate

Oakley Court

Castle Hotel Windsor

Cavendish House

The Crown And Cushion

Park Farm Bed and Breakfast

The Winning Post

Riverside bungalow, Hot Tub/Sauna, Nr Legoland, Windsor, Thorpe Park Theme Park.

Find out more about Windsor

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