Windsor Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Holiday Rentals in Windsor

2 bedrooms, iron/ironing board, travel cot, WiFi
Shipside Suite~Modern~ Fast WI-FI~Cozy

Shipside Suite~Modern~ Fast WI-FI~Cozy

Portsmouth
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 HK$405
HK$2,423 total
includes taxes & fees
4 Dec - 5 Dec
Shipside Suite~Modern~ Fast WI-FI~Cozy
2 bedrooms
Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News

2.0 star property
Newport News
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
Dining
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

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 HK$624
HK$2,048 total
includes taxes & fees
2 Dec - 3 Dec
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Fridge, microwave, oven, stovetop
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Portsmouth
10.0 out of 10, Exceptional, (15)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
The price is HK$1,100
HK$2,702 total
includes taxes & fees
14 Dec - 15 Dec
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Private kitchen
❤️The Safe House❤️Downtown Newport News!

❤️The Safe House❤️Downtown Newport News!

Newport News
8.8 out of 10, Excellent, (10)
"Quiet and a very cute posh spot. Everything was absolutely beautiful."
United States
chevon
❤️The Safe House❤️Downtown Newport News!
Beach
Cozy Suite - Pet Friendly, Beach Side 1 Bedroom Apts by RedAwning

Cozy Suite - Pet Friendly, Beach Side 1 Bedroom Apts by RedAwning

3.0 star property
Willoughby Spit
Cozy Suite - Pet Friendly, Beach Side 1 Bedroom Apts by RedAwning
Fridge, microwave, oven, stovetop
Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth

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 HK$789
HK$1,656 total
includes taxes & fees
1 Dec - 2 Dec
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Private kitchen
❤️Ice Ice Baby❤️Downtown Newport News!

❤️Ice Ice Baby❤️Downtown Newport News!

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 HK$490
HK$1,566 total
includes taxes & fees
2 Dec - 3 Dec
❤️Ice Ice Baby❤️Downtown Newport News!
Fridge, microwave, oven, stovetop
Large 2 bedroom | Queen beds | Safe Area

Large 2 bedroom | Queen beds | Safe Area

Wythe
7.8 out of 10, Good, (10)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is HK$798
HK$2,105 total
includes taxes & fees
1 Dec - 2 Dec
Large 2 bedroom | Queen beds | Safe Area
Fridge, microwave, oven, stovetop
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Portsmouth
9.0 out of 10, Wonderful, (22)
"Great property "
United States
Brian C.
The price is HK$779
HK$2,244 total
includes taxes & fees
1 Dec - 2 Dec
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Exterior
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

Franklin
9.8 out of 10, Exceptional, (40)
"Wonderful stay. This is a very cute and comfortable place. Will stay here again. "
United States
Denise P.
The price is HK$876
HK$1,249 total
includes taxes & fees
1 Dec - 2 Dec
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
2 bedrooms
The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News

2.0 star property
Newport News
The price is HK$574
HK$1,710 total
includes taxes & fees
2 Dec - 3 Dec
The Speakeasy Downtown Newport News
Fridge, microwave, oven, stovetop
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

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

Portsmouth
9.0 out of 10, Wonderful, (34)
"Easy access to everything"
United States
Latoya J.
The price is HK$856
HK$1,975 total
includes taxes & fees
1 Dec - 2 Dec
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Fridge, microwave, stovetop, coffee/tea maker
Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance

Suffolk
10.0 out of 10, Exceptional, (5)
"The property was clean, quiet and had everything we needed for a few days in town to see our grandbabies and daughter. Easy to find, park and just a few blocks from the highway, many food options and Kroger."
United States
Audrey J.
The price is HK$853
HK$1,859 total
includes taxes & fees
16 Dec - 17 Dec
Guesthouse in ideal location with private entrance
Fridge, microwave, oven, stovetop
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Portsmouth
8.8 out of 10, Excellent, (38)
"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 HK$1,004
HK$2,727 total
includes taxes & fees
1 Dec - 2 Dec
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Interior
4 Bedroom Cottage - 5 Minutes from both beaches

4 Bedroom Cottage - 5 Minutes from both beaches

Hampton
9.2 out of 10, Wonderful, (27)
"My overall stay was great! We loved the house and the host is super sweet! We had a minor issue with getting in touch with the host, but that was resolved. Definitely would book it again!"
United States
Anonymous traveller
The price is HK$1,079
HK$3,423 total
includes taxes & fees
1 Dec - 2 Dec
4 Bedroom Cottage - 5 Minutes from both beaches
Property grounds
Beautiful Spacious Downtown apt w/city views.

Beautiful Spacious Downtown apt w/city views.

2.5 star property
West Freemason
Beautiful Spacious Downtown apt w/city views.
Property grounds
*Mid/Long Term Rental* Cozy Home at Mary Roberts

*Mid/Long Term Rental* Cozy Home at Mary Roberts

2.0 star property
North Newport News
The price is HK$771
HK$2,348 total
includes taxes & fees
5 Dec - 6 Dec
*Mid/Long Term Rental* Cozy Home at Mary Roberts
Property grounds
Luxurious 2 Bed Queen Suite Near Downtown Norfolk

Luxurious 2 Bed Queen Suite Near Downtown Norfolk

Olde Huntersville
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.
Luxurious 2 Bed Queen Suite Near Downtown Norfolk
Smart TV
THE"HAVEN" (1 BEDROOM)

THE"HAVEN" (1 BEDROOM)

Franklin
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 HK$946
HK$1,735 total
includes taxes & fees
2 Dec - 3 Dec
THE"HAVEN" (1 BEDROOM)
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Hyatt Place Hampton Convention Center

Hyatt Place Hampton Convention Center

10/10 Excellent
"Great place to stay, comfortable and clean, with great customer service"
Marlene 4-night trip
Posted 5 hours ago
Hyatt Place Hampton Convention Center

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?

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 Suffolk Seaboard Station Railroad Museum and Windsor Castle Park.

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.