Holiday Rentals in Windsor

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Our top choices for Windsor holiday rentals

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (59 reviews)
"Beautiful and clean. The staff was amazing. "
United States
Robin
The price is €117
includes taxes & fees
18 Jan - 19 Jan
stayAPT Suites Suffolk-Chesapeake

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
The price is €203
includes taxes & fees
15 Jan - 16 Jan
Ice Ice Baby Downtown Newport News

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
10.0 out of 10, Exceptional, (16 reviews)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
The price is €258
includes taxes & fees
20 Jan - 21 Jan
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is €531
includes taxes & fees
15 Jan - 16 Jan
Centrally Located Hampton Roads Home w/ Game Room!

Water Front Delight on the Bay

Water Front Delight on the Bay
Willoughby Spit
7.8 out of 10, Good, (25 reviews)
"Everything was very nice really enjoyed "
United States
Deborah B.
The price is €285
includes taxes & fees
15 Jan - 16 Jan
Water Front Delight on the Bay

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 €164
includes taxes & fees
23 Jan - 24 Jan
Private 1 Bed Apt - Historic Olde Towne Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (4 reviews)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
The price is €231
includes taxes & fees
19 Jan - 20 Jan
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay,host was very hospital.love to enjoy it again in December "
United States
earnest d.
The price is €300
includes taxes & fees
15 Jan - 16 Jan
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

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 €240
includes taxes & fees
15 Jan - 16 Jan
Large 2 bedroom | Queen beds | Safe Area

Wooded Wonderland

Wooded Wonderland
Portsmouth
9.8 out of 10, Exceptional, (12 reviews)
"Well stocked and very clean. Beautiful home"
United States
Tammy K.
The price is €444
includes taxes & fees
18 Jan - 19 Jan
Wooded Wonderland

Luxurious 2 Bed Queen Suite Near Downtown Norfolk

Luxurious 2 Bed Queen Suite Near Downtown Norfolk
Olde Huntersville
7.0 out of 10, Good, (2 reviews)
"The stay was great. The apartment was just as pictured and described. All cooking utensils and silverware were in good working order. The location of the aprtment was the only questionable part of the stay. We were ultimately safe but the neighborhood did not give off those vibes. I wouldn't mind booking this vrbo again if it was just me and the boys but I wasn't super comfortable with the neighborhood with my wife and dog. Charlene was a great host though and super communicative."
United States
Cody D.
The price is €215
includes taxes & fees
13 Feb - 14 Feb
Luxurious 2 Bed Queen Suite Near Downtown Norfolk

The "KINGSDALE" 2 Bedrooms

The "KINGSDALE" 2 Bedrooms
Franklin
10.0 out of 10, Exceptional, (7 reviews)
"Nice place.Was clean and we had everything we needed. "
United States
Terri G.
The price is €241
includes taxes & fees
15 Jan - 16 Jan
The "KINGSDALE" 2 Bedrooms

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

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth
9.0 out of 10, Wonderful, (36 reviews)
"Old solid brick building. Don't build them like that anymore! Clean, quiet, comfortable. Great choice of restaurants close by and ferry service across river to Norfolk. Had a Great time "
United States
Daniel C.
The price is €228
includes taxes & fees
23 Jan - 24 Jan
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

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, (24 reviews)
"Great property "
United States
Brian C.
The price is €253
includes taxes & fees
1 Feb - 2 Feb
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Work Crew or Family-Friendly Lodging - 3 Bedrooms

Work Crew or Family-Friendly Lodging - 3 Bedrooms
Franklin
9.4 out of 10, Exceptional, (3 reviews)
"Nice quaint home, very comfortable. Had pictures and knick knacks around which made us feel right at home. Stayed here a week while exploring surrounding areas, the owners were quickly available with anything even though we did not have any problems needing addressed. Would definately stay here again if in the area."
United States
Mark C.
The price is €165
includes taxes & fees
18 Jan - 19 Jan
Work Crew or Family-Friendly Lodging - 3 Bedrooms

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)
"It was amazing. The house is dope, I highly recommend this house to anyone and I will be staying there again in the future!"
United States
Varstine S.
The price is €307
includes taxes & fees
22 Jan - 23 Jan
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

4 Bedroom Cottage - 5 Minutes from both beaches

4 Bedroom Cottage - 5 Minutes from both beaches
Hampton
9.2 out of 10, Wonderful, (27 reviews)
"Clean house. Very easy check in and out process. "
United States
Ryan P.
The price is €387
includes taxes & fees
15 Jan - 16 Jan
4 Bedroom Cottage - 5 Minutes from both beaches

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Willoughby Spit
7.8 out of 10, Good, (11 reviews)
"Loved the view and communication with owner was exceptional. "
United States
Dottie H.
The price is €433
includes taxes & fees
15 Jan - 16 Jan
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

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)
"This was our third year of staying at Jackie's place and once again had a great time. Our party of 9 had plenty of room including two dogs that loved the back yard. The fully stocked kitchen allowing for preparing food a breeze. The location was so convenient to grocery stores, restaurants and fast food!"
United States
Sherri J.
The price is €581
includes taxes & fees
18 Jan - 19 Jan
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)
"Was able to cook and relax for little getaway. "
United States
Rebecca S.
The price is €189
includes taxes & fees
15 Jan - 16 Jan
❤️Ice Ice Baby❤️Downtown Newport News!
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 €117 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 Windsor Castle Park.

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.