Windsor Holiday Rentals

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Holiday Rentals in Windsor

stayAPT Suites Suffolk-Chesapeake

2.5 star property
Suffolk
9.4 out of 10, Exceptional, (52)
"Nice cozy place to go with your family "
United States
Kesha
The price is NZ$241
includes taxes & fees
23 Nov - 24 Nov
stayAPT Suites Suffolk-Chesapeake

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

Willoughby Spit
7.8 out of 10, Good, (11)
"Location is great with a terrific view. House needs better upkeep and maintenance."
United States
Steve B.
The price is NZ$867
includes taxes & fees
18 Nov - 19 Nov
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Luxury Riverfront Condo w/ sunrise & sunset views

Kingsmill
9.6 out of 10, Exceptional, (68)
"Enjoyed my stay at this condo..I hope it becomes available again this year, "
United States
Orlanda
The price is NZ$613
includes taxes & fees
25 Nov - 26 Nov
Luxury Riverfront Condo w/ sunrise & sunset views

Manor and Mutts #2 - Beach Front, Pet Friendly, Wi-Fi, Parking, W/D, King Bed

Willoughby Spit
9.0 out of 10, Wonderful, (35)
"We love when VRBO hosts know how dogs can be an important part of the family! This was a very cute beach house that would suit a large family well. We enjoyed the beach access and the proximity to all that Norfolk has to offer. The host provided clear instructions for arrival and departure and the house included all that we needed for a weekend getaway. "
United States
Kristen O.
Manor and Mutts #2 - Beach Front, Pet Friendly, Wi-Fi, Parking, W/D, King Bed

Cozy Suite at the Beach

Willoughby Spit
8.4 out of 10, Very good, (62)
"Great stay"
United States
Kristin K.
Cozy Suite at the Beach

3 BEDROOM 2 BATH ON THE WATER

Willoughby Spit
9.4 out of 10, Exceptional, (75)
"Love this spot. Quite and relaxing. Host is awesome. This is definitely the spot, if you going to Norfolk Virginia. "
United States
Mr. Tony A. M.
3 BEDROOM 2 BATH ON THE WATER

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

Portsmouth
9.0 out of 10, Wonderful, (31)
"Easy access to everything"
United States
Latoya J.
The price is NZ$440
includes taxes & fees
18 Nov - 19 Nov
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

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

North Newport News
10.0 out of 10, Exceptional, (18)
"This place was beautiful and we had a great time "
United States
Robbi P.
The price is NZ$1,323
includes taxes & fees
18 Nov - 19 Nov
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

Kingsmill
9.8 out of 10, Exceptional, (151)
"Great location. "
United States
Kathryn T.
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

The Cracker Jack House: A Military Salute & Arcade!

Surry
9.2 out of 10, Wonderful, (20)
"Property was well maintained, arcade room is great for children. Host was quick to respond and help with any questions I had."
United States
Anthony O.
The Cracker Jack House: A Military Salute & Arcade!

Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Willoughby Spit
8.8 out of 10, Excellent, (106)
"Older property , plenty of space , "
United States
Carol
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

99) Massive home with Hot Tub!

Downtown Hampton
5.0 out of 10, (6)
"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 NZ$968
includes taxes & fees
16 Dec - 17 Dec
99) Massive home with Hot Tub!

History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

Surry
10.0 out of 10, Exceptional, (140)
"My mom, sisters and I thoroughly enjoyed our stay. The clean, welcoming property was so much fun to explore and enjoy. Staying at this historic property added so much charm to our vacation which included Jamestown and Williamsburg. We enjoyed taking the ferry each day and found this property to be in a great location. "
United States
Aleana R.
History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino

Portsmouth
9.0 out of 10, Wonderful, (11)
"Place was clean, check-in was easy and the backyard was great!"
United States
J. Drew L.
Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino

Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning

Willoughby Spit
7.6 out of 10, Good, (11)
"It was lovely home"
United States
Abigail S.
Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning

Uncle Bill's Lodge & Soccer Pool Showdown

Surry
9.0 out of 10, Wonderful, (12)
"The home was very comfortable for 5 of us with room to spare. Located in a friendly small town. Many extras included. There are many activities for kids. Our grandchildren had a great time, they would have liked to just stay at the property!. The ferry to Jamestown is very convenient and there is much to see on that side. We also visited the town of Smithfield which is only 20 minutes away. We were looking for a nice slow and relaxing pace and found it. "
United States
Deborah Q.
Uncle Bill's Lodge & Soccer Pool Showdown

Large 2 bedroom | Queen beds | Safe Area

Wythe
7.8 out of 10, Good, (10)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is NZ$478
includes taxes & fees
18 Nov - 19 Nov
Large 2 bedroom | Queen beds | Safe Area

Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private

Willoughby Spit
8.6 out of 10, Excellent, (14)
"Had a great time, very convenient beach access. Only complaint is there wasn’t a washer and dryer like the listing stated. Would definitely rent again."
United States
Kelsey H.
Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private

-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!

Newport News
The price is NZ$660
includes taxes & fees
23 Nov - 24 Nov
-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!

Massive 6 bedroom home in a great neighborhood!

Norfolk
4.6 out of 10, (4)
"They advertised a pool that doesn’t work, the kitchen is missing allot of items and the place was still dirty. Roof had a huge hole in the living room "
United States
Miguel F.
The price is NZ$1,110
includes taxes & fees
19 Nov - 20 Nov
Massive 6 bedroom home in a great neighborhood!
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, 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 NZ$241 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?

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!: This holiday home rental outside of Windsor has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 Chesapeake Square Mall and Planters Peanut Center.

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.