Default HTG hotel image

Windsor Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Windsor vacation 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.
$143 nightly
The price is $164
Nov 4 - Nov 5
Total with taxes and fees
Historical Suffolk Loft Apartment in Downtown Area
A small, single-story building with a porch, a seating area with chairs and a table, and a sign that reads 'welcome home'.

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, (50 reviews)
"A great little place! Peaceful, quiet. All necessities are available."
United States
Theresa G.
$141 nightly
The price is $152
Nov 4 - Nov 5
Total with taxes and fees
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
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.
$223 nightly
The price is $241
Nov 6 - Nov 7
Total with taxes and fees
Cozy 3-bedroom house in charming small town Sedley
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, (114 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
$119 nightly
The price is $137
Nov 9 - Nov 10
Total with taxes and fees
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.
$253 nightly
The price is $289
Nov 7 - Nov 8
Total with taxes and fees
Guesthouse in ideal location with private entrance
Private kitchen

6. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.2 out of 10, Wonderful, (39 reviews)
"Great stay! Will be staying again!"
United States
Wakeelah
$107 nightly
The price is $125
Nov 8 - Nov 9
Total with taxes and fees
stayAPT Suites Hampton
A living room with a fireplace, a television, a sofa, a coffee table, and a kitchen area in the background.

7. 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.
$243 nightly
The price is $262
Nov 9 - Nov 10
Total with taxes and fees
The "KINGSDALE" 2 Bedrooms
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

8. 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.
$226 nightly
The price is $263
Nov 20 - Nov 21
Total with taxes and fees
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A hotel room with a bed, a nightstand, a lamp, and a window with curtains.

9. 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 traveler
$66 nightly
The price is $78
Nov 5 - Nov 6
Total with taxes and fees
1 Queen Bed|Non-Smoking,Kitchen
A narrow brick pathway flanked by two houses with siding.

10. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (20 reviews)
"As described, clean, comfortable, and convenient! Will look to stay here again next time in the area."
United States
Mark D.
$154 nightly
The price is $180
Nov 8 - Nov 9
Total with taxes and fees
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window.

11. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
3.0 star property
Chesapeake
$552 nightly
The price is $637
Nov 9 - Nov 10
Total with taxes and fees
Entire Home in Chesapeake, Virginia
A modern living room with a wooden coffee table, a large white orchid, and a flat-screen TV.

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, (29 reviews)
"Great small home would rent again"
United States
Ronnie B.
$293 nightly
The price is $340
Nov 7 - Nov 8
Total with taxes and fees
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
A spacious lounge area with a chandelier, comfortable seating, and a prominent 'N. NEWS' sign on the wall.

13. Ice Ice Baby | Downtown Newport News!

Ice Ice Baby | Downtown Newport News!
Downtown Newport News
9.6 out of 10, Exceptional, (21 reviews)
"Over all stay was comfortable... and convenient! Traffic was good into Newport news... Good stay"
United States
Adria K.
$232 nightly
The price is $268
Nov 4 - Nov 5
Total with taxes and fees
Ice Ice Baby | Downtown Newport News!
A poolside area with a covered seating area, a pool, and a white fence.

14. 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
$197 nightly
The price is $229
Nov 4 - Nov 5
Total with taxes and fees
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

15. 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.
$243 nightly
The price is $282
Nov 4 - Nov 5
Total with taxes and fees
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window.

16. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
Chesapeake
$531 nightly
The price is $613
Nov 9 - Nov 10
Total with taxes and fees
Entire Home in Chesapeake, Virginia
A fireplace with a TV mounted above it, a Buddha statue, and a shelf with candles and a camera.

17. 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.
$227 nightly
The price is $262
Nov 4 - Nov 5
Total with taxes and fees
Cozy 1-bedroom condo in Hampton/AC NASA ,Air Force ,Army base Hampton U Norfolk
A golf course with a water body in the background, surrounded by trees and sand bunkers.

18. 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.
$280 nightly
The price is $316
Nov 4 - Nov 5
Total with taxes and fees
Luxury Riverfront Condo w/ sunrise & sunset views
A wooden deck with a railing overlooking a lake, surrounded by lush greenery.

19. 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.
$325 nightly
The price is $376
Nov 4 - Nov 5
Total with taxes and fees
3D Theater plus Dock on Small Lake
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

20. 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.
$506 nightly
The price is $585
Nov 8 - Nov 9
Total with taxes and fees
Wooded Wonderland
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
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

Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

10/10 Excellent
"The rooms were very clean and the staff was very helpful. The breakfast buffet was awesome."
Randall 1-night trip
Posted 1 hour ago
Embassy Suites by Hilton Hampton Convention Center

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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 vacation rental in Windsor?

Yes, we give you a choice of vacation rentals close to well known points of interest in Windsor, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Windsor has to offer?

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home: Visitors like this Windsor vacation home rental. It is located in the city center 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 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 larger area, you’ll find Windsor Castle Park and Chesapeake Square Mall.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can book for a couple days or more in Windsor. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.