Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

2.5 star property
9.4 out of 10, Exceptional, (55)
"The staff was so friendly. The rooms were so nice. I loved the kitchen and breakfast bar."
United States
Nicole
The price is AU$168
includes taxes & fees
28 Dec - 29 Dec
stayAPT Suites Suffolk-Chesapeake
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 AU$752
includes taxes & fees
30 Dec - 31 Dec
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
9.8 out of 10, Exceptional, (153)
"Owner was easy to work with, location was great, beautiful community and place was very clean. "
United States
Kathleen K.
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
9.6 out of 10, Exceptional, (70)
"Enjoyed my stay at this condo..I hope it becomes available again this year, "
United States
Orlanda
The price is AU$529
includes taxes & fees
30 Dec - 31 Dec
Luxury Riverfront Condo w/ sunrise & sunset views

Cottage in Willoughby Spit

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

Holiday Home in Willoughby Spit

3 BEDROOM 2 BATH ON THE WATER
9.4 out of 10, Exceptional, (75)
"My overall thoughts about this property, it was cozy and had a rustic, homey feel. It was spacious with a lovely backyard and the bay was perfect to sit and overlook at the beginning and end of the day. "
United States
Raelyn B.
3 BEDROOM 2 BATH ON THE WATER
9.0 out of 10, Wonderful, (35)
"We had a great time and were able to bring our dogs. This is a great place for adults "
United States
Rob B.
Manor and Mutts #2 - Beach Front, Pet Friendly, Wi-Fi, Parking, W/D, King Bed
10.0 out of 10, Exceptional, (154)
"Very nice property! We really enjoyed our time there. Would definitely stay there again!"
United States
Carmine S.
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
9.0 out of 10, Wonderful, (34)
"Easy access to everything"
United States
Latoya J.
The price is AU$381
includes taxes & fees
19 Jan - 20 Jan 2026
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
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
9.0 out of 10, Wonderful, (12)
"Great property. Very cool and chill host."
United States
John O.
Uncle Bill's Lodge & Soccer Pool Showdown

Holiday Home in Downtown Hampton

Hot Tub | 9 beds | Fenced Yard
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 AU$715
includes taxes & fees
22 Dec - 23 Dec
Hot Tub | 9 beds | Fenced Yard
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
9.2 out of 10, Wonderful, (21)
"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!
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
7.8 out of 10, Good, (10)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is AU$391
includes taxes & fees
20 Dec - 21 Dec
Large 2 bedroom | Queen beds | Safe Area
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.
Massive 6 bedroom home in a great neighborhood!
9.0 out of 10, Wonderful, (39)
"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 AU$520
includes taxes & fees
19 Jan - 20 Jan 2026
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
9.0 out of 10, Wonderful, (6)
"Would return again!"
United States
Parker L.
Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning
10.0 out of 10, Exceptional, (4)
"Very modern cottage, close to many things in the area. Loved that you had a hot water kettle and desks for WFH tasks."
United States
Laura C.
Beautiful, modern furnished 3-bedroom, 2-bathroom cottage near attractions.
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 favourite 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 depend 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 AU$168 per night. Entering your travel dates in the search wizard might find you 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?

Historic Old Towne Southern Charm: This holiday home rental outside of Windsor offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Suffolk Seaboard Station Railroad Museum and St. Luke's Church.

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.