Windsor Holiday Rentals from €193: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Windsor has to offer?

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home : This holiday home rental outside of Windsor is located in the city centre, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable 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.

Check Windsor holiday rental availability

Holiday Rentals in Windsor

"Quick weekend stay for a baby shower. The condo was clean and well stocked, host was very responsive. We enjoyed our stay."

"Lovely townhouse. No issues. Host very nice and communicated well. Walking distance to many things. Ferry to Norfolk, church and downtown restaurants and bars."

includes taxes & fees

2 Dec - 3 Dec

"We really liked Olde Town; the location was great, and close to the seawall and lots of historical buildings. The house itself was old and seemed a bit run-down (not everything worked), but the owners were responsive to addressing urgent concerns, and the price was good."

includes taxes & fees

26 Nov - 27 Nov

"The manager made a mistake. He owned it and gave us a better place. The parking could have been better. It served our purposes well. It was quiet and private. My husband fished every morning. Our first choice would not have been as nice."

includes taxes & fees

26 Nov - 27 Nov

"This place was so great to stay at!"

includes taxes & fees

30 Nov - 1 Dec

"Everything in the listing was exactly as shown. Check in and check out were simple and easy. Property manager was in contact and inquired of our needs. We didn't have any becuase the house was well stocked, but based on all other parts of the stay, I assume that would be handled efficiently. The highway is close, so there is quite a bit of road noise outside, but the sound is minimal once inside the house. We wpuld definitely stay here again."

includes taxes & fees

26 Dec - 27 Dec

"This property was perfect for our needs. Darling house with charm and convenience. Clean and well stocked. We loved our stay!"

"This was a great little place right on the water of the bay. At low tide we had a private tiny beach. It was in a great location and although it was in a very bisy area, it felt secluded. Everything we needed was there at yhe boathouse. It was clean and bright. The host was friendly and responsive immediately. He gave precise directions and we found the place easily in the dark. We had a lovely stay and would absolutely stay again. and was fr"

"This house was perfect for our extended family vacation. The house is very old but the owners made a lot very nice improvements. You can tell there are more things to do though. Communication was not that great but they were very nice when we did hear from them. Super easy check in"

includes taxes & fees

3 Dec - 4 Dec

"Perfectly clean and comfortable but no privacy. Pet friendly but neighbor allowed their dog to come to fenced yard at all hours which made my 1 dog bark. Not sure if neighbor was owner. Great fenced yard but as I stated, no privacy. Homes close by even in backyard. Fine for families who want to visit from out of town visiting Busch Gardens/Water Country and CW as backyard is entertaining and home is affordable. Just not what we were looking for. Photos and description made us feel it would be...

"The house looked exactly like the pictures we ran into a few problems but not with the host or the house we enjoyed our stay and it was pretty close to our homecoming I would definitely recommend, house was extremely clean "

"It was a great stay. Was there for work. Close for work and close to the beach. "

includes taxes & fees

15 Dec - 16 Dec

"Our family has stayed at a number of VRBO's in this general price range, and we were fairly pleased with each of them. This one was a step above the others. Everything was exactly as advertised. The house is big and as nice as the pictures indicate. Everything was well-maintained and very clean. The surrounding area is beautiful. There were no surprises. Everything that you would expect to work, worked great. Communication was prompt and very clear. The nearby ferry is very well run and...

"Kingsmill is a lovely property, very convenient to local attractions. The condo was clean and well furnished. "

"The property worked very well for our needs. "

"Sandwiched between Willoughby Bay and Willoughby Beach, this small 2-room unit offers a humble stay in an amazing location featuring many nearby locations including Virginia Beach and Jamestown (highly recommended). Just across the main street is a lovely, low-key beach with many artificial rock formations, creating multiple small bays that maintain warmer water. The main complaint would be the floor having a layer of dirt which could be easily solved by a quick mopping by the cleaners. We...

includes taxes & fees

2 Dec - 3 Dec

"Stayed here to visit my family for a wedding. The home was decorated nicely and bright. It was clean and quite. We enjoyed the game room and the kitchen had everything we needed to make meals as we didn't want to eat out every night. The listing was exactly as described. Thank you for hosting my family with your lovely home."

"Nice place to stay and close to ODU."

"Great property. Pool, hot tub and a very challenging mini putt-putt course. Furniture is in good shape and comfortable. One of the bedrooms has an adjustable bed ( same model as I have at home) so that was a very nice and welcomed surprise. We have ongoing business in the area so looking forward to staying here in the future. "

includes taxes & fees

26 Nov - 27 Nov

"The house is just as shown in the pictures. I was a little disappointed that there was no Ms Pacman video game, but that didn't ruin our stay. Communication was excellent. I would recommend this house to others. "

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Other types of properties in Windsor you may be interested in

Couples treatment room(s), sauna, hot tub, steam room, body treatments

"Beautiful property. Spacious rooms. Excellent staff who met all of our needs. "

includes taxes & fees

1 Dec - 2 Dec

Desk, laptop workspace, blackout curtains, iron/ironing board

"Enjoyed my stay, comfortable bed"

includes taxes & fees

25 Dec - 26 Dec

Hypo-allergenic bedding, desk, laptop workspace, iron/ironing board

"The location of this hotel is perfect for visiting downtown Norfolk. You can walk to many restaurants and attractions. The staff was very friendly and helpful and made the weekend one we won’t forget. "

includes taxes & fees

8 Dec - 9 Dec

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 €193 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.

Recent reviews of Windsor properties

5/5 Excellent

"Easy to enter and exit, check-in and checkout."

A verified traveller stayed at Comfort Suites Airport

Posted 2 days ago

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?

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home: This holiday home rental outside of Windsor is located in the city centre, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable 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.

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.

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Holiday Rentals in Windsor

Check Windsor holiday rental availability

Holiday Rentals in Windsor

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

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

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

Cozy Suite at the Beach

Hilton Village Home

Sojourn | Coastal Cottage | 3 BR

Charming 2 bed 1 bath near Langley Air Force Base

The Boat House on the Bay - On the water; Pet Friendly; WiFi

Private Estate on 4 Acres

Uncle Bill's Lodge & Soccer Pool Showdown

Beautiful 4bedroom vacation pool home, where relaxation & indulgence intertwine.

Comfortable & Private 2 Bedrm Cottage w/ King bed.

James River Waterfront with spectacular views across the river from Williamsburg

Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!

Comfy stylish townhome

Studio Apt. at the Boat House - Water Front, Pet Friendly, WiFi, Smart TV

5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room

Magnificent 2 Bedroom Home in Norfolk's Best Neighborhood

Wooded Wonderland

The Cracker Jack House: A Military Salute & Arcade!

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Find out more about Windsor

Recent reviews of Windsor properties

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Frequently asked questions