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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Windsor holiday rentals

A two-story brick house with a front porch, a garage, and a well-maintained lawn.

1. 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, (12 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
24 Sept - 25 Sept
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 welcome sign.

2. 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, (48 reviews)
"A great little place! Peaceful, quiet. All necessities are available."
United States
Theresa G.
The price is HK$883
HK$1,258 total
includes taxes & fees
28 Sept - 29 Sept
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
A living room with a fireplace, a television, a sofa, a coffee table, and a kitchen area in the background.

3. The "KINGSDALE" 2 Bedrooms

The "KINGSDALE" 2 Bedrooms
Franklin
10.0 out of 10, Exceptional, (9 reviews)
"We loved staying at the "KINGSDALE" during our recent visit to Franklin VA. The house was immaculate and the host was very responsive and the check-in and check-out process was super easy. I highly recommend!"
United States
Stan C.
The price is HK$1,412
HK$2,169 total
includes taxes & fees
27 Sept - 28 Sept
The "KINGSDALE" 2 Bedrooms
A modern courtyard with white furniture, a central seating area, and a small lawn.

4. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (105 reviews)
"This property was like a home away from home. Rooms were spacious and location was good. Host was very friendly."
United States
Karen
The price is HK$934
HK$1,072 total
includes taxes & fees
5 Oct - 6 Oct
stayAPT Suites Suffolk-Chesapeake
A modern kitchen with white cabinets, a built-in oven, and a dining area with a gray sofa and a table.

5. 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$2,280 total
includes taxes & fees
3 Oct - 4 Oct
Guesthouse in ideal location with private entrance
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

6. 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, (30 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$792
HK$2,279 total
includes taxes & fees
28 Sept - 29 Sept
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A living room with a beige sofa, a white ottoman, a patterned rug, a wooden chair, and a small table.

7. 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, (12 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$1,006
HK$1,686 total
includes taxes & fees
24 Sept - 25 Sept
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

8. 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$2,436
HK$5,053 total
includes taxes & fees
27 Sept - 28 Sept
Wooded Wonderland
A multi-story building with balconies, a courtyard with seating, and a well-maintained lawn.

9. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.6 out of 10, Exceptional, (19 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is HK$934
HK$1,089 total
includes taxes & fees
24 Sept - 25 Sept
stayAPT Suites Hampton
A living room with a sectional sofa, a round ottoman, a globe on a shelf, and artwork on the walls.

10. Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.2 out of 10, Wonderful, (27 reviews)
"Great small home would rent again"
United States
Ronnie B.
The price is HK$918
HK$2,703 total
includes taxes & fees
26 Sept - 27 Sept
Comfortable & Private 2 Bedrm Cottage w/ King bed.
A glass-top table with two cushioned chairs on a wooden deck, a vase with red flowers, and a brick wall.

11. 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, (55 reviews)
"Comfortable home and clean quiet stay. "
United States
Lisa H.
The price is HK$981
HK$2,099 total
includes taxes & fees
24 Sept - 25 Sept
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

12. 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)
"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$698
HK$2,153 total
includes taxes & fees
20 Oct - 21 Oct
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A narrow brick pathway flanked by two houses with siding.

13. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (14 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$1,458 total
includes taxes & fees
27 Sept - 28 Sept
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A beach with a sandy shore, a water body, and a few people.

14. Family friendly 5 bedroom home within Walking distance To CNU

Family friendly 5 bedroom home within Walking distance To CNU
Central Newport News
10.0 out of 10, Exceptional, (57 reviews)
"The property is very well maintained and clean. Ample parking for multiple cars. The host is a great communicator and available to answer any questions you may have."
United States
Anonymous traveller
The price is HK$5,021
HK$7,324 total
includes taxes & fees
29 Sept - 30 Sept
Family friendly 5 bedroom home within Walking distance To CNU
A modern kitchen with a sink, hanging plants, and a pendant light.

15. -NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!

-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!
Newport News
9.6 out of 10, Exceptional, (12 reviews)
"Everything was very clean good coffee options plenty of hot water :)"
United States
Allen C.
The price is HK$3,130
HK$4,726 total
includes taxes & fees
29 Sept - 30 Sept
-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!
A waterfront view from a wooden deck with a white railing, a dock extending into the water, and a clear blue sky.

16. Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
8.8 out of 10, Excellent, (6 reviews)
The price is HK$1,758
HK$3,642 total
includes taxes & fees
27 Sept - 28 Sept
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
A modern kitchen with stainless steel appliances, a dining area with a blue sofa, and a small outdoor garden with a waterfall.

17. 8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
North Newport News
10.0 out of 10, Exceptional, (25 reviews)
"The nursery was great. The kitchen was well appointed. Did not care for the pans with removable handles. More comfortable living room seating would be nice. But overall a lovely home."
United States
Otis G.
The price is HK$4,442
HK$6,667 total
includes taxes & fees
5 Oct - 6 Oct
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
A two-story house with a porch, a covered front entry, and a small front yard with landscaping.

18. Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Coliseum Central
9.6 out of 10, Exceptional, (44 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is HK$2,224
HK$4,432 total
includes taxes & fees
24 Sept - 25 Sept
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

19. Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.0 out of 10, Very good, (47 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is HK$1,012
HK$2,712 total
includes taxes & fees
1 Oct - 2 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
A beach with a sandy shore, a water body, and a few people.

20. 5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis

5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis
Hampton
9.8 out of 10, Exceptional, (42 reviews)
"So many great rooms. Loved the waterfall"
United States
Dwayne W.
The price is HK$4,825
HK$6,980 total
includes taxes & fees
19 Oct - 20 Oct
5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis
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 Suites Airport

Comfort Suites Airport

10/10 Excellent
"I was pleasantly surprised to find the room truly clean.Well maintained- updated furniture,bedspreads, paint on walls not scuffed or dirty. Shades not dusty or stained. Completely satisfied and thankful for a great overnite stay. Staff was pleasant!"
delece 1-night trip
Posted 6 hours ago
Comfort Suites Airport

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.