Holiday Rentals in Windsor

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Our top choices for Windsor holiday rentals

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (4 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
The price is €164
includes taxes & fees
15 Jun - 16 Jun
Private 1 Bed Apt - Historic Olde Towne Portsmouth

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (82 reviews)
"Very clean and modern room at a very reasonable price. We will definitely stay there again if we are in that area."
United States
Scott
The price is €118
includes taxes & fees
18 Jun - 19 Jun
stayAPT Suites Suffolk-Chesapeake

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is €287
includes taxes & fees
8 Jun - 9 Jun
The Speakeasy Downtown Newport News

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 €230
includes taxes & fees
16 Jun - 17 Jun
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.6 out of 10, Exceptional, (21 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is €291
includes taxes & fees
8 Jun - 9 Jun
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (5 reviews)
"The property was clean, quiet and had everything we needed for a few days in town to see our grandbabies and daughter. Easy to find, park and just a few blocks from the highway, many food options and Kroger."
United States
Audrey J.
The price is €209
includes taxes & fees
21 Jun - 22 Jun
Guesthouse in ideal location with private entrance

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, (28 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is €274
includes taxes & fees
15 Jun - 16 Jun
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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, (45 reviews)
"Wonderful property!"
United States
Virginia G.
The price is €142
includes taxes & fees
8 Jun - 9 Jun
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

The Magnolia JEM With A Private Entrance

The Magnolia JEM With A Private Entrance
Suffolk
The price is €226
includes taxes & fees
15 Jun - 16 Jun
The Magnolia JEM With A Private Entrance

THE"HAVEN" (1 BEDROOM)

THE"HAVEN" (1 BEDROOM)
Franklin
9.6 out of 10, Exceptional, (7 reviews)
"Every time we stay it is very clean, well stocked, easy to enter and very quiet. "
United States
Neomia L.
The price is €193
includes taxes & fees
12 Jun - 13 Jun
THE"HAVEN" (1 BEDROOM)

Hot Tub | 9 beds | Fenced Yard

Hot Tub | 9 beds | Fenced Yard
Downtown Hampton
5.2 out of 10, (7 reviews)
"The house served its purpose for a weekend stay. Quite a few quirks to the property. Close to downtown Hampton. "
United States
Regina P.
The price is €513
includes taxes & fees
8 Jun - 9 Jun
Hot Tub | 9 beds | Fenced Yard

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, (6 reviews)
"It’s was great staying "
United States
Shalena K.
The price is €218
includes taxes & fees
7 Jun - 8 Jun
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
7.4 out of 10, Good, (3 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
Ice Ice Baby Downtown Newport News

❤️Ice Ice Baby❤️Downtown Newport News!

❤️Ice Ice Baby❤️Downtown Newport News!
Downtown Newport News
9.4 out of 10, Exceptional, (20 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!

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 €291
includes taxes & fees
15 Jun - 16 Jun
Large 2 bedroom | Queen beds | Safe Area

Work Crew or Family-Friendly Lodging - 3 Bedrooms

Work Crew or Family-Friendly Lodging - 3 Bedrooms
Franklin
9.6 out of 10, Exceptional, (5 reviews)
"Property was nice. The house was clean."
United States
Rhonda A.
The price is €165
includes taxes & fees
29 Jun - 30 Jun
Work Crew or Family-Friendly Lodging - 3 Bedrooms

The "KINGSDALE" 2 Bedrooms

The "KINGSDALE" 2 Bedrooms
Franklin
10.0 out of 10, Exceptional, (8 reviews)
"We loved staying at the "KINGSDALE" during our recent visit to Franklin VA. The house was immaculate and the host was very responsive and the check-in and check-out process was super easy. I highly recommend!"
United States
Stan C.
The price is €241
includes taxes & fees
7 Jun - 8 Jun
The "KINGSDALE" 2 Bedrooms

8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
North Newport News
10.0 out of 10, Exceptional, (22 reviews)
"Was a great place for families with adults and children. (12,10,8). 10 min or so to Busch Gardens. "
United States
Dwayne R.
The price is €804
includes taxes & fees
23 Jun - 24 Jun
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

Wooded Wonderland

Wooded Wonderland
Portsmouth
9.8 out of 10, Exceptional, (13 reviews)
"Easy check in. House very clean and well equipped. Comfortable stay"
United States
Nona C.
The price is €655
includes taxes & fees
8 Jun - 9 Jun
Wooded Wonderland

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 €349
includes taxes & fees
12 Jun - 13 Jun
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
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 €118 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?

Cozy 4 Bed 2 Bath Home - Norfolk, Centrally Located: This holiday home rental outside of Windsor has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

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 Suffolk Center for Cultural Arts.

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.