Search Vacation Homes in Windsor

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 268 Vacation Homes in Windsor with updated reviews, rates, and availability.

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

9.2 out of 10, Wonderful, (27)
"I’mi liked my stay ; everything was fine and the host communicated well with me…"
The price is AED 628
AED 1,489 total
includes taxes & fees
28 Apr - 29 Apr
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

NEW! Big Waterfront House w/ Amazing View and Swim Deck

2.0 out of 10, (1)
"I actually did not stay on the property because host cancelled at the last minute and put me in another home ( his mother's house) When I arrived there was someone at the house. It was overbooked and host did not even tell me. I had to call. Left me without a place to stay. "
NEW! Big Waterfront House w/ Amazing View and Swim Deck

Sojourn | Coastal Cottage | 3 BR

9.4 out of 10, Exceptional, (28)
"The house was so adorable! We loved our stay there and would absolutely stay again."
The price is AED 518
AED 1,438 total
includes taxes & fees
5 May - 6 May
Sojourn | Coastal Cottage | 3 BR

Charming 4-bedroom bungalow with AC and WiFi in Hampton, with washer and dryer.

Charming 4-bedroom bungalow with AC and WiFi in Hampton, with washer and dryer.

Historic Old Towne Southern Charm

9.8 out of 10, Exceptional, (12)
"Very clean and a great location "
Historic Old Towne Southern Charm

The Cracker Jack House: A Military Salute & Arcade!

9.4 out of 10, Exceptional, (11)
"Our stay was excellent. We really enjoyed the game room and firepit. The house was very clean and comfortable. We also had lots of fun listening to music on the jukebox. "
The Cracker Jack House: A Military Salute & Arcade!

Spacious 7-bedroom house in brilliant Newport News with AC, WiFi

10.0 out of 10, Exceptional, (1)
The price is AED 3,853
AED 5,427 total
includes taxes & fees
24 May - 25 May
Spacious 7-bedroom house in brilliant Newport News with AC, WiFi

Family friendly in Hampton with huge yard, dog park, and 2 blocks from the bay

Family friendly in Hampton with huge yard, dog park, and 2 blocks from the bay

Pleasurable Escape Hampton

9.4 out of 10, Exceptional, (14)
"My grandaughter was in a swim meet at the Aquaplex for that week and we decided to make a vacation of it. Location was great. Close to beach, stores, and Aquaplex. Great time was had by all"
Pleasurable Escape Hampton

The Mermaids Lair 🧜‍♀️

8.8 out of 10, Excellent, (6)
"What an incredible lil gem of a stay. This place is perfect for 1-2 person short stay. The views are incredible and the place was clean and welcoming - the bed was so comfortable! It is a small space but the design is just perfect. Quiet, safe area and I will definitely be back. Only suggestion would be to add a hair dryer. "
The Mermaids Lair 🧜‍♀️

Experience Timeless Luxury at Cavalier Manor on a Lake

10.0 out of 10, Exceptional, (2)
"I had a small wedding at this property, and let me tell you that it was the wedding of my dreams. From the beautiful interior to the extravagant exterior, my guest was amazed at the beauty of this home. We also stayed a total of five days and the property manager checked on us regularly to make sure we had a comfortable stay. I cannot express how thoughtful and beautiful this home is. I wish I could stay forever. I highly recommend this property."
Experience Timeless Luxury at Cavalier Manor on a Lake

Waterfront Home w/ Dock & Yard in Hampton!

10.0 out of 10, Exceptional, (3)
"This house was wonderful. It was everything we needed for the weekend. "
Waterfront Home w/ Dock & Yard in Hampton!

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

7.6 out of 10, Good, (8)
"Great location with a back yard facing the bay and an easy 2 block walk to the beach. Clean, spacious home that was great for our group."
Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning

Beachfront House on James River. Near Historic Jamestowne and Williamsburg

10.0 out of 10, Exceptional, (193)
"The house was spotless and the hosts answered any questions we had right away! The kitchen was well stocked and beds were comfortable. Such a beautiful view from this spot! We enjoyed our time here very much."
Beachfront House on James River. Near Historic Jamestowne and Williamsburg

The Great Gatsby: Pink Flamingo Lounge Retreat!

2.0 star property
8.4 out of 10, Very Good, (5)
"The property was clean and well-maintained, and in a convenient location near Williamsburg, Smithfield and other historic locations. Access to the Jamestowne-Scotland ferry was great."
The Great Gatsby: Pink Flamingo Lounge Retreat!

Oasis at the Creek

10.0 out of 10, Exceptional, (1)
"Great interior, well appointed property with a large backyard. Very happy we stayed here. "
Oasis at the Creek

James River Waterfront with spectacular views across the river from Williamsburg

10.0 out of 10, Exceptional, (133)
"Lovely house with beautiful sunrise. Close to attractions but away from hustle and bustle of big city."
James River Waterfront with spectacular views across the river from Williamsburg

New listing! Sleeps 10, short walk to the beach!

10.0 out of 10, Exceptional, (1)
"Fun"
New listing! Sleeps 10, short walk to the beach!

Centrally Located Hampton Home: 6 Mi to Downtown!

9.8 out of 10, Exceptional, (11)
"The home was very nice. The host was very nice and accessible. "
Centrally Located Hampton Home: 6 Mi to Downtown!

Huge water view 2/2 condo in "Kingsmill on the James"

10.0 out of 10, Exceptional, (61)
"What a great place to stay roomy,super clean. Great location easy to rent and find. Nice place to stay close to lot of places. The owner decorated for Christmas what nice touch when you walk in"
Huge water view 2/2 condo in "Kingsmill on the James"
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Windsor

stayAPT Suites Suffolk-Chesapeake

2.5 star property
10.0 out of 10, Exceptional, (12)
"Great place to stay!"
The price is AED 433
AED 497 total
includes taxes & fees
28 Apr - 29 Apr
stayAPT Suites Suffolk-Chesapeake

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

9.6 out of 10, Exceptional, (19)
"The apartment was charming; however, it could use some updating. The location was excellent, quiet, and easy access to local stores and restaurants. Ideal for a short stay. "
The price is AED 404
AED 945 total
includes taxes & fees
1 May - 2 May
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

9.2 out of 10, Wonderful, (27)
"I’mi liked my stay ; everything was fine and the host communicated well with me…"
The price is AED 628
AED 1,489 total
includes taxes & fees
28 Apr - 29 Apr
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
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.