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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Windsor holiday rentals

Exterior detail

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 NZ$311
includes taxes & fees
15 Nov - 16 Nov
Historical Suffolk Loft Apartment in Downtown Area
A gazebo with a covered patio, surrounded by well-maintained grass and a white picket fence.

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, (51 reviews)
"Host was very helpful in everything"
United States
Jackie M.
The price is NZ$274
includes taxes & fees
15 Nov - 16 Nov
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
Room

3. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (119 reviews)
"Room was clean, very nice and quiet property. Loved staying here and will recommend anyone who visits the area"
United States
olivia
The price is NZ$247
includes taxes & fees
15 Dec - 16 Dec
stayAPT Suites Suffolk-Chesapeake
Interior

4. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.2 out of 10, Wonderful, (42 reviews)
"Great stay! Will be staying again!"
United States
Wakeelah
The price is NZ$239
includes taxes & fees
15 Nov - 16 Nov
stayAPT Suites Hampton
A two-story brick house with a front porch, a garage, and a well-maintained lawn.

5. 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 NZ$430
includes taxes & fees
15 Nov - 16 Nov
Cozy 3-bedroom house in charming small town Sedley
A house with a covered porch, two red chairs, a small statue, and a staircase with a metal railing.

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 NZ$464
includes taxes & fees
23 Nov - 24 Nov
The "KINGSDALE" 2 Bedrooms
A kitchen with white cabinets, a stainless steel sink, a granite countertop, a stove, and a coffee maker.

7. Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (7 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 NZ$521
includes taxes & fees
15 Nov - 16 Nov
Guesthouse in ideal location with private entrance
A small house with a red door, a window with blinds, a wooden table and chairs, a black lamp, and a striped rug.

8. 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, (29 reviews)
"We really enjoyed our stay! The house was cozy and the perfect size for the three of us. While we didn't do any cooking, the kitchen appeared to have everything you would need. The shower had great hot water, which was nice after a long day. The neighborhood was quiet and peaceful, and there were several good restaurants nearby, making it easy to grab a meal. We'd definitely stay here again!"
United States
Allan S.
The price is NZ$613
includes taxes & fees
15 Nov - 16 Nov
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
A living room with a glass coffee table, two leather chairs, a desk, and a green door.

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
9.4 out of 10, Exceptional, (10 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 NZ$439
includes taxes & fees
23 Nov - 24 Nov
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A poolside area with a covered seating area, a pool, and a white fence.

10. 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 NZ$426
includes taxes & fees
1 Dec - 2 Dec
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A modern living room with a large window, a flat-screen TV, a desk, and a sofa.

11. The Speakeasy | Downtown Newport News!

The Speakeasy | Downtown Newport News!
Downtown Newport News
9.0 out of 10, Wonderful, (20 reviews)
"Such a great place! We will visit again"
United States
Candice C.
The price is NZ$468
includes taxes & fees
15 Nov - 16 Nov
The Speakeasy | Downtown Newport News!
A narrow brick pathway flanked by two houses with siding.

12. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (21 reviews)
"As described, clean, comfortable, and convenient! Will look to stay here again next time in the area."
United States
Mark D.
The price is NZ$311
includes taxes & fees
16 Nov - 17 Nov
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A staircase with a wooden handrail and white balusters, carpeted steps, and a white door with a stained glass window.

13. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
3.0 star property
Chesapeake
The price is NZ$1,173
includes taxes & fees
29 Nov - 30 Nov
Entire Home in Chesapeake, Virginia
A hotel room with a bed, a nightstand, a lamp, and a window with curtains.

14. 1 Queen Bed|Non-Smoking,Kitchen

1 Queen Bed|Non-Smoking,Kitchen
Coliseum Central
10.0 out of 10, Exceptional, (3 reviews)
"Check-in was quick and room dark enough for good sleep. Compact kitchen had what I needed."
United States
Anonymous traveller
The price is NZ$144
includes taxes & fees
19 Nov - 20 Nov
1 Queen Bed|Non-Smoking,Kitchen
A golf course with a water body in the background, surrounded by trees and sand bunkers.

15. Luxury Riverfront Condo w/ sunrise & sunset views

Luxury Riverfront Condo w/ sunrise & sunset views
Kingsmill
9.8 out of 10, Exceptional, (87 reviews)
"The host were very accommodating and helpful. Close to everything."
United States
Michelle g.
The price is NZ$596
includes taxes & fees
16 Nov - 17 Nov
Luxury Riverfront Condo w/ sunrise & sunset views
A wooden deck with a railing overlooking a lake, surrounded by lush greenery.

16. 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.
The price is NZ$695
includes taxes & fees
15 Nov - 16 Nov
3D Theater plus Dock on Small Lake
A modern kitchen with grey cabinets, a stainless steel microwave, a built-in oven, and a granite countertop.

17. 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, (33 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 NZ$492
includes taxes & fees
30 Nov - 1 Dec
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A compact kitchen with a stove, cabinets, and a refrigerator.

18. Cozy 1-bedroom condo in Hampton/AC NASA ,Air Force ,Army base Hampton U Norfolk

Cozy 1-bedroom condo in Hampton/AC NASA ,Air Force ,Army base Hampton U Norfolk
Hampton
10.0 out of 10, Exceptional, (1 review)
"Very good location and quite clean"
United States
Kyle L.
The price is NZ$475
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom condo in Hampton/AC NASA ,Air Force ,Army base Hampton U Norfolk
A staircase with a wooden handrail and white balusters, carpeted steps, and a white door with a stained glass window.

19. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
Chesapeake
The price is NZ$1,090
includes taxes & fees
6 Dec - 7 Dec
Entire Home in Chesapeake, Virginia
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

20. 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, (15 reviews)
"Jason made us feel welcome and the check-in process was very easy. Communication was made throughout our stay and Jason was available for anything we needed."
United States
Timothy R.
The price is NZ$595
includes taxes & fees
15 Nov - 16 Nov
Bright 3-bedroom beach house with AC in charming Norfolk
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 Suffolk - Chesapeake

Comfort Suites Suffolk - Chesapeake

10/10 Excellent
"The area where the and how the breakfast is laid out"
Adrian 1-night trip
Posted 1 day ago
Comfort Suites Suffolk - Chesapeake

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as NZ$239 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.