Default HTG hotel image

Windsor Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windsor vacation rentals

Terrace/patio

1. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (104 reviews)
"Perfect! Will stay again and will look for this brand in my future travels."
United States
Melissa
$119 nightly
The price is $137
Sep 7 - Sep 8
Total with taxes and fees
stayAPT Suites Suffolk-Chesapeake
Coffee/tea maker, fridge, microwave, stovetop

2. 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
Sep 6 - Sep 7
Total with taxes and fees
Guesthouse in ideal location with private entrance
Property grounds

3. 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, (47 reviews)
"A great little place! Peaceful, quiet. All necessities are available."
United States
Theresa G.
$149 nightly
The price is $160
Sep 11 - Sep 12
Total with taxes and fees
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
Property grounds

4. 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, (53 reviews)
"Comfortable home and clean quiet stay. "
United States
Lisa H.
$239 nightly
The price is $278
Sep 7 - Sep 8
Total with taxes and fees
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Coffee/tea maker, fridge, microwave, oven

5. 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.
$275 nightly
The price is $319
Sep 14 - Sep 15
Total with taxes and fees
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Exterior

6. 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.
$233 nightly
The price is $252
Sep 25 - Sep 26
Total with taxes and fees
Cozy 3-bedroom house in charming small town Sedley
Private kitchen

7. ❤️Ice Ice Baby❤️Downtown Newport News!

❤️Ice Ice Baby❤️Downtown Newport News!
Downtown Newport News
9.4 out of 10, Exceptional, (20 reviews)
"Over all stay was comfortable... and convenient! Traffic was good into Newport news... Good stay"
United States
Adria K.
$240 nightly
The price is $259
Sep 7 - Sep 8
Total with taxes and fees
❤️Ice Ice Baby❤️Downtown Newport News!
Smart TV, fireplace

8. 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.
$257 nightly
The price is $278
Sep 10 - Sep 11
Total with taxes and fees
The "KINGSDALE" 2 Bedrooms
Dining

9. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Little too cold for swimming but the pool was beautiful. House was very clean and comfortable. We had 8 staying and we didn’t feel on top of each other. One of our party left her jewelry behind but the owner was great and arrangements where made to get them back to her. Would definitely stay again!"
United States
Dawn J.
$555 nightly
The price is $641
Sep 7 - Sep 8
Total with taxes and fees
Wooded Wonderland
Coffee/tea maker, fridge, microwave, oven

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

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.2 out of 10, Very Good, (45 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
$301 nightly
The price is $349
Sep 7 - Sep 8
Total with taxes and fees
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Property grounds

11. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (11 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
$159 nightly
The price is $186
Sep 7 - Sep 8
Total with taxes and fees
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Coffee/tea maker, fridge, microwave, oven

12. -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.
$524 nightly
The price is $604
Sep 9 - Sep 10
Total with taxes and fees
-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!
House | 2 bedrooms

13. Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
7.4 out of 10, Good, (3 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
$225 nightly
The price is $260
Sep 7 - Sep 8
Total with taxes and fees
Ice Ice Baby Downtown Newport News
Property grounds

14. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
10.0 out of 10, Exceptional, (9 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
$117 nightly
The price is $136
Oct 4 - Oct 5
Total with taxes and fees
stayAPT Suites Hampton
Smart TV, fireplace

15. 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
8.6 out of 10, Excellent, (11 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
$190 nightly
The price is $222
Sep 8 - Sep 9
Total with taxes and fees
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Smart TV, DVD player

16. 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.
$290 nightly
The price is $337
Sep 7 - Sep 8
Total with taxes and fees
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Private kitchen

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

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
7.4 out of 10, Good, (3 reviews)
"Great house"
United States
sarah a.
$401 nightly
The price is $464
Sep 7 - Sep 8
Total with taxes and fees
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Living area

18. Beautiful, spacious home in welcoming Norfolk.

Beautiful, spacious home in welcoming Norfolk.
Norfolk
7.4 out of 10, Good, (3 reviews)
"Host was great, very responsive. The house was great and very clean. Very quiet neighborhood. Short drive to everything Norfolk and Virginia Beach had to offer."
United States
shereece t.
$530 nightly
The price is $613
Sep 5 - Sep 6
Total with taxes and fees
Beautiful, spacious home in welcoming Norfolk.
Exterior

19. 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.
$587 nightly
The price is $677
Sep 28 - Sep 29
Total with taxes and fees
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Golf

20. Luxury Riverfront Condo w/ sunrise & sunset views

Luxury Riverfront Condo w/ sunrise & sunset views
Kingsmill
9.8 out of 10, Exceptional, (83 reviews)
"It was a great spot to stay during graduation. We enjoyed the views and option to be able to be away from all the hustle and bustle on campus. Being on resort with the option of going to the restaurants was very nice and the owner was very good to work with."
United States
Greg M.
$308 nightly
The price is $347
Sep 7 - Sep 8
Total with taxes and fees
Luxury Riverfront Condo w/ sunrise & sunset views
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

The Landing at Hampton Marina, Tapestry Collection by Hilton

The Landing at Hampton Marina, Tapestry Collection by Hilton

8/10 Good
"The staff was great, the restaurant was a welcome benefit to a weary traveler, and the room was clean and comfortable. Expedia should note there is a $15 daily parking fee to use the hotel garage."
capt scott 1-night trip
Posted 5 hours ago
The Landing at Hampton Marina, Tapestry Collection by Hilton

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 $136 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?

Bright 3-bedroom beach house with AC in charming Norfolk: Visitors like this Windsor vacation home rental. It offers a fireplace, a patio, and a barbecue grill 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 Planters Peanut Center 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.