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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Windsor holiday rentals

Interior

1. Historical Suffolk Loft Apartment in Downtown Area

Historical Suffolk Loft Apartment in Downtown Area
Suffolk
9.0 out of 10, Wonderful, (4 reviews)
"Beautiful property and close to everything."
United States
Linda W.
The price is HK$980
HK$1,420 total
includes taxes & fees
27 Oct - 28 Oct
Historical Suffolk Loft Apartment in Downtown Area
A modern courtyard with white furniture, a central seating area, and a small lawn.

2. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (113 reviews)
"Theophilus was great at check in. Amazing customer service, quick check-in. The place was clean, the rooms were very clean. The overall atmosphere was great. I will definitely stay here again."
United States
Tarina
The price is HK$933
HK$1,072 total
includes taxes & fees
9 Nov - 10 Nov
stayAPT Suites Suffolk-Chesapeake
A two-story brick house with a front porch, a garage, and a well-maintained lawn.

3. Cozy 3-bedroom house in charming small town Sedley

Cozy 3-bedroom house in charming small town Sedley
Sedley
10.0 out of 10, Exceptional, (15 reviews)
"Very nice spot to stay. The host was excellent!"
United States
Wade H.
The price is HK$1,412
HK$1,991 total
includes taxes & fees
26 Oct - 27 Oct
Cozy 3-bedroom house in charming small town Sedley
A small, single-story building with a porch, a seating area with chairs and a table, and a sign that reads 'welcome home'.

4. 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, (49 reviews)
"A great little place! Peaceful, quiet. All necessities are available."
United States
Theresa G.
The price is HK$882
HK$1,258 total
includes taxes & fees
26 Oct - 27 Oct
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
A modern bathroom with a shower, toilet, and sink.

5. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.0 out of 10, Wonderful, (32 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is HK$933
HK$1,089 total
includes taxes & fees
26 Oct - 27 Oct
stayAPT Suites Hampton
A living room with a fireplace, a television, a sofa, a coffee table, and a kitchen area in the background.

6. The "KINGSDALE" 2 Bedrooms

The "KINGSDALE" 2 Bedrooms
Franklin
10.0 out of 10, Exceptional, (11 reviews)
"Nice place.Was clean and we had everything we needed. "
United States
Terri G.
The price is HK$1,412
HK$2,151 total
includes taxes & fees
26 Oct - 27 Oct
The "KINGSDALE" 2 Bedrooms
A modern kitchen with white cabinets, a built-in oven, and a dining area with a gray sofa and a table.

7. Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (6 reviews)
"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$941
HK$2,279 total
includes taxes & fees
7 Nov - 8 Nov
Guesthouse in ideal location with private entrance
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window.

8. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
2.0 star property
Chesapeake
The price is HK$1,529
HK$5,084 total
includes taxes & fees
9 Nov - 10 Nov
Entire Home in Chesapeake, Virginia
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

9. 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
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect experience for our vacation and we highly recommend this property and the host was so easy to get in contact with!"
United States
Coachmeech Gaming O.
The price is HK$628
HK$2,063 total
includes taxes & fees
1 Nov - 2 Nov
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

10. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Great property not too far from the beaches! Between the pool, hot tub, mini golf, and theater room, our family had plenty to do at the house when we weren't out exploring Virginia Beach. Owner was quick to respond to any questions or needs as well."
United States
Erin W.
The price is HK$2,040
HK$4,804 total
includes taxes & fees
27 Oct - 28 Oct
Wooded Wonderland
A living room with a beige sofa, a white ottoman, a patterned rug, a wooden chair, and a small table.

11. Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
8.8 out of 10, Excellent, (13 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
The price is HK$1,118
HK$1,886 total
includes taxes & fees
6 Nov - 7 Nov
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Living area

12. Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!

Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
Portsmouth
9.2 out of 10, Wonderful, (27 reviews)
"Great small home would rent again"
United States
Ronnie B.
The price is HK$847
HK$2,702 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
A spacious living room with a fireplace, a television, and a view of the outdoors.

13. Luxury Riverfront Condo w/ sunrise & sunset views

Luxury Riverfront Condo w/ sunrise & sunset views
Kingsmill
9.8 out of 10, Exceptional, (87 reviews)
"The condo was perfect! Great location, beautiful views, clean and spacious. The pull out sofa was surprisingly large and very comfortable. It was exactly what we expected based on the photos."
United States
Cynthia K.
The price is HK$1,334
HK$2,731 total
includes taxes & fees
26 Oct - 27 Oct
Luxury Riverfront Condo w/ sunrise & sunset views
A wooden deck with a railing overlooking a lake, surrounded by lush greenery.

14. 3D Theater plus Dock on Small Lake

3D Theater plus Dock on Small Lake
Portsmouth
8.6 out of 10, Excellent, (4 reviews)
"Very nice property. Quiet neighborhood with a beautiful lake view."
United States
Muun Queen M.
3D Theater plus Dock on Small Lake
A spacious lounge area with a large chandelier, comfortable seating, and a prominent 'N. NEWS' sign on the wall.

15. Breakfast @ Tiffany's | Downtown Newport News!

Breakfast @ Tiffany's | Downtown Newport News!
Downtown Newport News
9.0 out of 10, Wonderful, (6 reviews)
"Everything was easy and the location was great."
United States
Caressa W.
The price is HK$857
HK$2,329 total
includes taxes & fees
26 Oct - 27 Oct
Breakfast @ Tiffany's | Downtown Newport News!
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

16. Bright 3-bedroom beach house with AC in charming Norfolk

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.6 out of 10, Exceptional, (14 reviews)
"The property is spacious and conveniently located near the beach and restaurants. It is family-friendly and the host is exceptionally communicative. I plan to return in the future."
United States
Sheryll
The price is HK$791
HK$2,642 total
includes taxes & fees
26 Oct - 27 Oct
Bright 3-bedroom beach house with AC in charming Norfolk
A modern kitchen with white cabinets, stainless steel appliances, a double sink, and a window with a view.

17. Spacious Portsmouth Getaway w/Game Room

Spacious Portsmouth Getaway w/Game Room
Portsmouth
8.0 out of 10, Very good, (3 reviews)
"This house was the perfect fit for our weekend getaway. My husband was a volunteer at Farm Aid and my son and I brought the dog and had a nice little weekend. It was clean and just as the host described. All the amenities were there. We would stay again if we were in the area."
United States
Susan L.
The price is HK$1,059
HK$3,081 total
includes taxes & fees
26 Oct - 27 Oct
Spacious Portsmouth Getaway w/Game Room
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

18. 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
9.2 out of 10, Wonderful, (32 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is HK$847
HK$2,341 total
includes taxes & fees
16 Nov - 17 Nov
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A bedroom with a bed, bedside lamps, a ceiling fan, a window with curtains, a door, and a trash can.

19. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (17 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
The price is HK$635
HK$1,481 total
includes taxes & fees
29 Oct - 30 Oct
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A modern living room with a fireplace, a kitchen in the background, and a dining area with bar stools.

20. Quiet & Private, Comfy Beds, Fire Pit, & Bikes

Quiet & Private, Comfy Beds, Fire Pit, & Bikes
Portsmouth
8.4 out of 10, Very good, (6 reviews)
"Home was perfect for my husband and I and our adult daughter and plenty of room when our other daughter and husband visited. We had enough room to eat and play games. Great yard for dogs to run, sniff and play! Beds were comfy. "
United States
Marybeth T.
The price is HK$1,137
HK$3,180 total
includes taxes & fees
26 Oct - 27 Oct
Quiet & Private, Comfy Beds, Fire Pit, & Bikes
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
"Very clean, the staff were attentive and always happy to help. My 3 days their were pleasant and I used their small fitness room which was great to have available along with my coffee and breakfast every morning."
Jennifer 3-night trip
Posted 15 hours 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:

  • View our selection of featured holiday rentals in Windsor
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  • 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?

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 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.