Windsor Holiday Rentals

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Holiday Rentals in Windsor

Ice Ice Baby Downtown Newport News
2.0 star property
10.0 out of 10, Exceptional, (2)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
Ice Ice Baby Downtown Newport News
Comfortable & Private 2 Bedrm Cottage w/ King bed.
10.0 out of 10, Exceptional, (14)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
The price is AU$506
includes taxes & fees
26 Oct - 27 Oct
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Shipside Suite~Modern~ Fast WI-FI~Cozy
10.0 out of 10, Exceptional, (1)
"Very good communication with the host Area was quiet. Rental very clean & well stocked. Was a very enjoyable stay! "
United States
Rheta P.
The price is AU$461
includes taxes & fees
28 Oct - 29 Oct
Shipside Suite~Modern~ Fast WI-FI~Cozy
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
9.6 out of 10, Exceptional, (4)
"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 AU$408
includes taxes & fees
26 Oct - 27 Oct
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Private 1 Bed Apt - Historic Olde Towne Portsmouth
10.0 out of 10, Exceptional, (2)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
The price is AU$328
includes taxes & fees
26 Oct - 27 Oct
Private 1 Bed Apt - Historic Olde Towne Portsmouth
❤️Breakfast @ Tiffany's❤️Downtown Newport News!
8.8 out of 10, Excellent, (5)
"Cool little place, large bathroom and living spaces.. Near restaurants and quiet too."
United States
Nathan H.
The price is AU$343
includes taxes & fees
27 Oct - 28 Oct
❤️Breakfast @ Tiffany's❤️Downtown Newport News!
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
9.0 out of 10, Wonderful, (31)
"Cozy apartment in historic Portsmouth. Great for families - lovely, walkable neighborhood. 7-10 min from downtown Norfolk. "
United States
Zeynep Ivet B.
The price is AU$401
includes taxes & fees
26 Oct - 27 Oct
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
9.2 out of 10, Wonderful, (19)
"Nice, comfortable stay. Communication with renter was fantastic. Clean rooms and clam neighborhood."
United States
David V.
The price is AU$447
includes taxes & fees
11 Nov - 12 Nov
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Large 2 bedroom | Queen beds | Safe Area
7.8 out of 10, Good, (10)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is AU$435
includes taxes & fees
27 Oct - 28 Oct
Large 2 bedroom | Queen beds | Safe Area
❤️The Safe House❤️Downtown Newport News!
8.8 out of 10, Excellent, (10)
"Quiet and a very cute posh spot. Everything was absolutely beautiful."
United States
chevon
The price is AU$329
includes taxes & fees
27 Oct - 28 Oct
❤️The Safe House❤️Downtown Newport News!
The Speakeasy Downtown Newport News
2.0 star property
The Speakeasy Downtown Newport News
THE"HAVEN" (1 BEDROOM)
9.6 out of 10, Exceptional, (7)
"Every time we stay it is very clean, well stocked, easy to enter and very quiet. "
United States
Neomia L.
The price is AU$342
includes taxes & fees
26 Oct - 27 Oct
THE"HAVEN" (1 BEDROOM)
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
9.0 out of 10, Wonderful, (37)
"This was a great stay. The location was nice and quiet. Loved the ability to walk to several eateries and bars. Thoroughly enjoyed our stay. Had a great time and the owners were very responsive. "
United States
Sarah G.
The price is AU$542
includes taxes & fees
27 Oct - 28 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
9.8 out of 10, Exceptional, (39)
"Great little home "
United States
david b.
The price is AU$249
includes taxes & fees
27 Oct - 28 Oct
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
❤️Ice Ice Baby❤️Downtown Newport News!
9.4 out of 10, Exceptional, (18)
"Was able to cook and relax for little getaway. "
United States
Rebecca S.
The price is AU$329
includes taxes & fees
27 Oct - 28 Oct
❤️Ice Ice Baby❤️Downtown Newport News!
The "KINGSDALE" 2 Bedrooms
10.0 out of 10, Exceptional, (6)
"House looked just like the pictures very clean. The Host is very helpful and replys quickly! We will definitely stay again at their places"
United States
Cindy M.
The price is AU$426
includes taxes & fees
26 Oct - 27 Oct
The "KINGSDALE" 2 Bedrooms
stayAPT Suites Suffolk-Chesapeake
2.5 star property
9.4 out of 10, Exceptional, (50)
"Nice cozy place to go with your family "
United States
Kesha
The price is AU$210
includes taxes & fees
28 Oct - 29 Oct
stayAPT Suites Suffolk-Chesapeake
Luxurious 2 Bed Queen Suite Near Downtown Norfolk
7.0 out of 10, Good, (2)
"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 AU$461
includes taxes & fees
26 Oct - 27 Oct
Luxurious 2 Bed Queen Suite Near Downtown Norfolk
Luxury Riverfront Condo w/ sunrise & sunset views
9.6 out of 10, Exceptional, (67)
"Enjoyed my stay at this condo..I hope it becomes available again this year, "
United States
Orlanda
The price is AU$540
includes taxes & fees
27 Oct - 28 Oct
Luxury Riverfront Condo w/ sunrise & sunset views
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
10.0 out of 10, Exceptional, (1)
"Enjoyed our stay,host was very hospital.love to enjoy it again in December "
United States
earnest d.
The price is AU$663
includes taxes & fees
2 Nov - 3 Nov
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, 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$210 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?

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 Windsor Castle Park 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.