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Our top choices for Windsor holiday rentals

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (26 reviews)
"Great stay, host is very responsive to issues and concerns "
United States
Jackson H.
The price is £217
includes taxes & fees
22 Apr - 23 Apr
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth
9.2 out of 10, Wonderful, (39 reviews)
"Beautiful place, beautiful location "
United States
rocco m.
The price is £201
includes taxes & fees
26 Mar - 27 Mar
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is £185
includes taxes & fees
26 Mar - 27 Mar
The Speakeasy Downtown Newport News

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
The price is £141
includes taxes & fees
29 Mar - 30 Mar
Private 1 Bed Apt - Historic Olde Towne Portsmouth

❤️The Safe House❤️Downtown Newport News!

❤️The Safe House❤️Downtown Newport News!
Downtown Newport News
8.8 out of 10, Excellent, (11 reviews)
"Quiet and a very cute posh spot. Everything was absolutely beautiful."
United States
chevon
❤️The Safe House❤️Downtown Newport News!

Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (34 reviews)
"The house was clean and had everything you need. The neighborhood was quiet. Beach access was just a short walk away and not crowded. "
United States
Daniel P.
The price is £306
includes taxes & fees
14 Apr - 15 Apr
Sojourn | Coastal Cottage | 3 BR

4 Bedroom Cottage - 5 Minutes from both beaches

4 Bedroom Cottage - 5 Minutes from both beaches
Hampton
9.4 out of 10, Exceptional, (29 reviews)
"Clean house. Very easy check in and out process. "
United States
Ryan P.
The price is £481
includes taxes & fees
23 Apr - 24 Apr
4 Bedroom Cottage - 5 Minutes from both beaches

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
9.4 out of 10, Exceptional, (3 reviews)
"It’s was great staying "
United States
Shalena K.
The price is £151
includes taxes & fees
29 Mar - 30 Mar
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.4 out of 10, Exceptional, (18 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is £219
includes taxes & fees
31 Mar - 1 Apr
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
9.0 out of 10, Wonderful, (39 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is £253
includes taxes & fees
31 Mar - 1 Apr
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Large 2 bedroom | Queen beds | Safe Area

Large 2 bedroom | Queen beds | Safe Area
Wythe
7.8 out of 10, Good, (10 reviews)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is £238
includes taxes & fees
21 Apr - 22 Apr
Large 2 bedroom | Queen beds | Safe Area

Large cozy private room

Large cozy private room
Marshall
The price is £122
includes taxes & fees
29 Mar - 30 Mar
Large cozy private room

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
10.0 out of 10, Exceptional, (2 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
Ice Ice Baby Downtown Newport News

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Coliseum Central
9.6 out of 10, Exceptional, (42 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is £398
includes taxes & fees
26 Mar - 27 Mar
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

❤️Ice Ice Baby❤️Downtown Newport News!

❤️Ice Ice Baby❤️Downtown Newport News!
Downtown Newport News
9.4 out of 10, Exceptional, (19 reviews)
"We had a great trip. Loved the industrial look and feel of the apartment. The bed was super comfy and the location was great. It was so convenient to go to the restaurants a few doors down. "
United States
Linda B.
❤️Ice Ice Baby❤️Downtown Newport News!

Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
Franklin
9.8 out of 10, Exceptional, (43 reviews)
"Wonderful stay. This is a very cute and comfortable place. Will stay here again. "
United States
Denise P.
The price is £122
includes taxes & fees
6 Apr - 7 Apr
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

Luxury Riverfront Condo w/ sunrise & sunset views

Luxury Riverfront Condo w/ sunrise & sunset views
Kingsmill
9.6 out of 10, Exceptional, (74 reviews)
"Lovely view of river and the woods. Marina has nice view of river and tasty food. Also like that it’s close to Jamestown and Downtown Williamsburg."
United States
Jeffrey
The price is £255
includes taxes & fees
26 Mar - 27 Mar
Luxury Riverfront Condo w/ sunrise & sunset views

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (69 reviews)
"perfect stay. would definitely stay again "
United States
berry
The price is £102
includes taxes & fees
21 Apr - 22 Apr
stayAPT Suites Suffolk-Chesapeake

Blue Octopus

Blue Octopus
Willoughby Spit
7.0 out of 10, Good, (2 reviews)
"It was a great time, we loved the pool and location, place was very comfortable and spacious. Thank you for everything."
United States
Alpha S.
The price is £350
includes taxes & fees
29 Mar - 30 Mar
Blue Octopus

Wooded Wonderland

Wooded Wonderland
Portsmouth
9.8 out of 10, Exceptional, (12 reviews)
"Easy check in. House very clean and well equipped. Comfortable stay"
United States
Nona C.
The price is £402
includes taxes & fees
26 Mar - 27 Mar
Wooded Wonderland
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 £102 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 a holiday rental 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?

5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room : This holiday home rental outside of Windsor is located next to a golf course, and has a patio, a garden and a BBQ 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Windsor?

Cultural attractions include Boykin's Tavern, whereas Lake Prince is a spot to enjoy nature. In the wider area, you’ll find Planters Peanut Center and Chesapeake Square Mall.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.