Holiday Rentals in Windsor

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Holiday Rentals in Windsor

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.4 out of 10, Exceptional, (49)
"Nice cozy place to go with your family "
The price is €118
includes taxes & fees
30 Oct - 31 Oct
stayAPT Suites Suffolk-Chesapeake

Cozy Suite at the Beach

8.4 out of 10, Very good, (61)
"It was alright "
Cozy Suite at the Beach

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

7.4 out of 10, Good, (10)
"Attentive helped with any concerns within minutes. Would reccomend! "
The price is €499
includes taxes & fees
10 Nov - 11 Nov
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

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

9.0 out of 10, Wonderful, (29)
"Me and a friend were in town for a concert and decided to arrive the night before and leave the next of the event, this house was perfect and had so much character to it, being in the historic part of Portsmouth, we knew exactly what to expect! If we ever go back that away, we will definitely rent it again."
The price is €226
includes taxes & fees
10 Nov - 11 Nov
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

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

9.8 out of 10, Exceptional, (147)
"Great location very clean and cozy room. Beautiful area!!"
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (66)
"Enjoyed my stay at this condo..I hope it becomes available again this year, "
The price is €309
includes taxes & fees
20 Oct - 21 Oct
Luxury Riverfront Condo w/ sunrise & sunset views

Manor and Mutts #2 - Beach Front, Pet Friendly, High Speed WiFi

9.0 out of 10, Wonderful, (35)
"We had a wonderful time here. Easy booking and check in. Host was very responsive. Got everything needed from kitchen, bedroom and bbq grill.The beach was lovely too, not crowded with beautiful sunset. Over all it was a great weekend stay for all of us."
Manor and Mutts #2 - Beach Front, Pet Friendly, High Speed WiFi

3 BEDROOM 2 BATH ON THE WATER

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. "
3 BEDROOM 2 BATH ON THE WATER

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

9.8 out of 10, Exceptional, (22)
"The house was perfect for our family to enjoy a high school graduation. Had our own space and plenty of bathrooms "
5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room

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."
The price is €244
includes taxes & fees
12 Oct - 13 Oct
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Perfect for families!

6.6 out of 10, (8)
"we enjoy the stay and we’ll book again great location located right behind the Newport police station. There’s also lots of things to do in the location. A big pond for fishing my family enjoyed."
The price is €267
includes taxes & fees
13 Oct - 14 Oct
Perfect for families!

Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi

8.8 out of 10, Excellent, (48)
"Property was clean and well appointed. Love that it was pet-friendly. Would definitely consider staying again. Would recommend. Suggestions: replace carpet with laminate or hard wood floors - would be easier to clean and hypoallergenic. Blinds on the windows would help the natural lighting and privacy. Thanks again. "
Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi

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

10.0 out of 10, Exceptional, (150)
"We enjoyed our stay! Very nice place."
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!

Beachhouse

2.6 out of 10, (4)
"I made two bookings, very easy but one canceled abruptly and the second turned out to be a non-available property and I did not find out until an before check-in. I was credited 100 for my trouble. I recommend that anyone that chooses this method, to reach out to the management agency or owner immediately to get the actual status of the property."
Beachhouse

Pleasurable Escape Hampton

9.4 out of 10, Exceptional, (21)
"The house was spotless and accommodations just as advertised. Thanks for a restful vacation home."
Pleasurable Escape Hampton

Crown Jewel in the Neighborhood.

8.0 out of 10, Very good, (7)
"The house was clean, plenty of room to relax. Beds are comfortable, quiet neighborhood. "
Crown Jewel in the Neighborhood.

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

8.8 out of 10, Excellent, (103)
"Older property , plenty of space , "
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Boat House Studio - Water Front Pets WiFi Smart TV by RedAwning

2.0 out of 10, (1)
"The pictures are inaccurate.A family was staying right at the deck.The grilling area is in rough shape.I will purchase canceling insurance for now on because of this property.Very outdated.Needs some money put into it.It has good potential but a no thankyou for me.Parking was terrible for me as I had a big work truck.And outdated appliances.Live and learn."
Boat House Studio - Water Front Pets WiFi Smart TV by RedAwning

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. "
The price is €309
includes taxes & fees
10 Nov - 11 Nov
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Riverfront Fun: Quiet Home Near Hampton Coastline

3.0 star property
Riverfront Fun: Quiet Home Near Hampton Coastline
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?

5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room : This holiday home rental outside of Windsor is located next to a golf course, and has a patio, a garden and a BBQ to put you at ease 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.