Windsor Vacation Rentals

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Vacation Rentals in Windsor

stayAPT Suites Suffolk-Chesapeake

2.5 star property
Suffolk
9.4 out of 10, Exceptional, (53)
"Nice cozy place to go with your family "
United States
Kesha
$113 nightly
The price is $130
Dec 29 - Dec 30
Total with taxes and fees
stayAPT Suites Suffolk-Chesapeake

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Willoughby Spit
7.8 out of 10, Good, (11)
"Location is great with a terrific view. House needs better upkeep and maintenance."
United States
Steve B.
$432 nightly
The price is $500
Dec 1 - Dec 2
Total with taxes and fees
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Luxury Riverfront Condo w/ sunrise & sunset views

Kingsmill
9.6 out of 10, Exceptional, (68)
"Enjoyed my stay at this condo..I hope it becomes available again this year, "
United States
Orlanda
$309 nightly
The price is $348
Dec 1 - Dec 2
Total with taxes and fees
Luxury Riverfront Condo w/ sunrise & sunset views

Manor and Mutts #2 - Beach Front, Pet Friendly, Wi-Fi, Parking, W/D, King Bed

Willoughby Spit
9.0 out of 10, Wonderful, (35)
"We had a great time and were able to bring our dogs. This is a great place for adults "
United States
Rob B.
Manor and Mutts #2 - Beach Front, Pet Friendly, Wi-Fi, Parking, W/D, King Bed

Cozy Suite at the Beach

Willoughby Spit
8.4 out of 10, Very Good, (62)
"Great stay"
United States
Kristin K.
Cozy Suite at the Beach

3 BEDROOM 2 BATH ON THE WATER

Willoughby Spit
9.4 out of 10, Exceptional, (75)
"My overall thoughts about this property, it was cozy and had a rustic, homey feel. It was spacious with a lovely backyard and the bay was perfect to sit and overlook at the beginning and end of the day. "
United States
Raelyn B.
3 BEDROOM 2 BATH ON THE WATER

Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

Kingsmill
9.8 out of 10, Exceptional, (152)
"Great stay! 2nd time using this VRBO listing & again fabulous stay. Well appointed room with good size refrigerator and microwave. Owners responded promptly to any inquires I had. Definitely a place to consider at The Kingsmill! "
United States
Jean Z.
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Portsmouth
9.0 out of 10, Wonderful, (32)
"Easy access to everything"
United States
Latoya J.
$220 nightly
The price is $256
Nov 30 - Dec 1
Total with taxes and fees
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

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

North Newport News
10.0 out of 10, Exceptional, (18)
"Beautiful, spacious, well appointed home. Met all the needs from baby to 4 adults. Very comfortable beds. Highly recommend and would stay again if in the area. You won’t be disappointed. "
United States
DENA H.
$662 nightly
The price is $762
Dec 1 - Dec 2
Total with taxes and fees
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Willoughby Spit
8.8 out of 10, Excellent, (106)
"Older property , plenty of space , "
United States
Carol
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

The Cracker Jack House: A Military Salute & Arcade!

Surry
9.2 out of 10, Wonderful, (20)
"Property was well maintained, arcade room is great for children. Host was quick to respond and help with any questions I had."
United States
Anthony O.
The Cracker Jack House: A Military Salute & Arcade!

Uncle Bill's Lodge & Soccer Pool Showdown

Surry
9.0 out of 10, Wonderful, (12)
"Host was very effective with communication. "
United States
Kenzie H.
Uncle Bill's Lodge & Soccer Pool Showdown

History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

Surry
10.0 out of 10, Exceptional, (140)
"We had a wonderful stay at this beautiful historical home! From the timeless antiques to the peaceful views, every detail made our time here so special. Our children especially loved exploring and discovering little treasures throughout the house and grounds, while we enjoyed the quiet, relaxing atmosphere. It was truly a refreshing and memorable getaway. We are so grateful for the hospitality and highly recommend this charming place to anyone. "
United States
Mikaela P.
History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

99) Massive home with Hot Tub!

Downtown Hampton
5.0 out of 10, (6)
"The house served its purpose for a weekend stay. Quite a few quirks to the property. Close to downtown Hampton. "
United States
Regina P.
$511 nightly
The price is $521
Dec 7 - Dec 8
Total with taxes and fees
99) Massive home with Hot Tub!

Beautiful, modern furnished 3-bedroom, 2-bathroom cottage near attractions.

Portsmouth
10.0 out of 10, Exceptional, (3)
"Working in Chesapeake and staying in this property has been great! The owners have been very communicative through our stay! Close to everything we have needed even close to the beach (25 min away). If you are going to Porstmouth area you should stay here. We will be back for certain "
United States
Jay H.
Beautiful, modern furnished 3-bedroom, 2-bathroom cottage near attractions.

Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino

Portsmouth
9.0 out of 10, Wonderful, (11)
"Place was clean, check-in was easy and the backyard was great!"
United States
J. Drew L.
Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino

Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!

Kingsmill
10.0 out of 10, Exceptional, (153)
"Very nice property! We really enjoyed our time there. Would definitely stay there again!"
United States
Carmine S.
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!

Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning

Willoughby Spit
7.6 out of 10, Good, (11)
"It was lovely home"
United States
Abigail S.
Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning

Large 2 bedroom | Queen beds | Safe Area

Wythe
7.8 out of 10, Good, (10)
"Clean, convenient and comfortable, would stay again."
United States
Riley
$265 nightly
The price is $269
Nov 30 - Dec 1
Total with taxes and fees
Large 2 bedroom | Queen beds | Safe Area

Massive 6 bedroom home in a great neighborhood!

Norfolk
4.6 out of 10, (4)
"They advertised a pool that doesn’t work, the kitchen is missing allot of items and the place was still dirty. Roof had a huge hole in the living room "
United States
Miguel F.
$628 nightly
The price is $639
Nov 30 - Dec 1
Total with taxes and fees
Massive 6 bedroom home in a great neighborhood!
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

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 $130 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?

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!: Visitors like this Windsor vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 Suffolk Seaboard Station Railroad Museum and Windsor Castle Park.

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.