Windsor Holiday Rentals

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Check prices for these dates

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov

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
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$342
HK$2,336 total
includes taxes & fees
19 Oct - 20 Oct
Shipside Suite~Modern~ Fast WI-FI~Cozy
Fridge, microwave, oven, stovetop
Comfortable & Private 2 Bedrm Cottage w/ King bed.
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 HK$988
HK$2,535 total
includes taxes & fees
19 Oct - 20 Oct
Comfortable & Private 2 Bedrm Cottage w/ King bed.
2 bedrooms
Ice Ice Baby Downtown Newport News
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
The price is HK$917
HK$2,160 total
includes taxes & fees
21 Oct - 22 Oct
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
9.4 out of 10, Exceptional, (3)
"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$622
HK$2,043 total
includes taxes & fees
23 Oct - 24 Oct
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
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!!
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 HK$699
HK$2,141 total
includes taxes & fees
21 Oct - 22 Oct
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Fridge, microwave, oven, stovetop
Private 1 Bed Apt - Historic Olde Towne 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 HK$875
HK$1,762 total
includes taxes & fees
8 Nov - 9 Nov
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Smart TV, offices
❤️Breakfast @ Tiffany's❤️Downtown Newport News!
❤️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 HK$575
HK$1,656 total
includes taxes & fees
19 Oct - 20 Oct
❤️Breakfast @ Tiffany's❤️Downtown Newport News!
Exterior
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
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 HK$874
HK$1,246 total
includes taxes & fees
19 Oct - 20 Oct
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
Property grounds
Large 2 bedroom | Queen beds | Safe Area
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 HK$889
HK$2,212 total
includes taxes & fees
20 Oct - 21 Oct
Large 2 bedroom | Queen beds | Safe Area
Fridge, microwave, oven, stovetop
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
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 HK$1,002
HK$2,677 total
includes taxes & fees
28 Oct - 29 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Property grounds
Luxurious 2 Bed Queen Suite Near Downtown Norfolk
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 HK$1,049
HK$2,310 total
includes taxes & fees
20 Oct - 21 Oct
Luxurious 2 Bed Queen Suite Near Downtown Norfolk
Smart TV
THE"HAVEN" (1 BEDROOM)
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 HK$944
HK$1,731 total
includes taxes & fees
19 Oct - 20 Oct
THE"HAVEN" (1 BEDROOM)
2 bedrooms
The Speakeasy Downtown Newport News
The Speakeasy Downtown Newport News
2.0 star property
The price is HK$880
HK$2,110 total
includes taxes & fees
20 Oct - 21 Oct
The Speakeasy Downtown Newport News
Property grounds
The "KINGSDALE" 2 Bedrooms
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 HK$1,398
HK$2,148 total
includes taxes & fees
19 Oct - 20 Oct
The "KINGSDALE" 2 Bedrooms
Terrace/patio
stayAPT Suites Suffolk-Chesapeake
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 HK$814
HK$936 total
includes taxes & fees
11 Nov - 12 Nov
stayAPT Suites Suffolk-Chesapeake
Private kitchen
❤️Ice Ice Baby❤️Downtown Newport News!
❤️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 HK$590
HK$1,674 total
includes taxes & fees
19 Oct - 20 Oct
❤️Ice Ice Baby❤️Downtown Newport News!
Interior
4 Bedroom Cottage - 5 Minutes from both beaches
4 Bedroom Cottage - 5 Minutes from both beaches
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$1,938
HK$4,496 total
includes taxes & fees
28 Oct - 29 Oct
4 Bedroom Cottage - 5 Minutes from both beaches
TV
Perfect for families!
Perfect for families!
6.6 out of 10, (9)
"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."
United States
Lakeshia O.
The price is HK$771
HK$2,240 total
includes taxes & fees
19 Oct - 20 Oct
Perfect for families!
Smart TV, fireplace
Wooded Wonderland
Wooded Wonderland
9.8 out of 10, Exceptional, (11)
"Well stocked and very clean. Beautiful home"
United States
Tammy K.
The price is HK$2,413
HK$4,818 total
includes taxes & fees
19 Oct - 20 Oct
Wooded Wonderland
Fridge, microwave, oven, stovetop
Family friendly 5 bedroom home within Walking distance To CNU
Family friendly 5 bedroom home within Walking distance To CNU
10.0 out of 10, Exceptional, (48)
"We had the most amazing time in this beautiful modern house! The rooms were perfect, the common area and living room are more beautiful than the pictures and the water feature outside is so peaceful! I couldn’t recommend staying here more! "
United States
Julie B.
The price is HK$3,325
HK$4,937 total
includes taxes & fees
21 Oct - 22 Oct
Family friendly 5 bedroom home within Walking distance To CNU
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

Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

10/10 Excellent
"I love the front desk team, staff, hospitality was amazing! I will always stay here when I come into town. My grandkids love it too. Especially the pool everything was superb!"
Tomika 3-night trip
Posted 3 days ago
Comfort Inn & Suites Hampton near Coliseum

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:

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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 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.