Windsor Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Holiday Rentals in Windsor

stayAPT Suites Suffolk-Chesapeake
Terrace/patio

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 HK$926
HK$1,063 total
includes taxes & fees
26 Oct - 27 Oct
stayAPT Suites Suffolk-Chesapeake
Cozy Suite at the Beach
On the beach, sun-loungers

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!
Terrace/patio

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 HK$2,327
HK$4,346 total
includes taxes & fees
12 Oct - 13 Oct
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Fridge, microwave, oven, stovetop

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 HK$856
HK$1,974 total
includes taxes & fees
19 Oct - 20 Oct
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Property grounds

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
Marina

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 HK$1,324
HK$2,710 total
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
On the beach

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
Outdoor dining

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
Fridge, microwave, oven, stovetop

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!!
Fridge, microwave, oven, stovetop

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 HK$700
HK$2,144 total
includes taxes & fees
12 Oct - 13 Oct
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Perfect for families!
TV

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 HK$967
HK$2,439 total
includes taxes & fees
20 Oct - 21 Oct
Perfect for families!
Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi
On the beach

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!
Beach nearby, beach towels

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
Marina

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
Fridge, microwave, oven, stovetop

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.
Private kitchen

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

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
Property grounds

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
Fridge, microwave, oven, stovetop

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 HK$1,004
HK$2,726 total
includes taxes & fees
13 Oct - 14 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Riverfront Fun: Quiet Home Near Hampton Coastline
Interior

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

Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

10/10 Excellent
"All was fine "
Mary Jane 2-night trip
Posted 3 days ago
Embassy Suites by Hilton Hampton Convention Center

Find out more about Windsor

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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.