Search Vacation Homes in Windsor

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Homes in Windsor

Our top choices for Windsor vacation homes

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

7.6 out of 10, Good, (8)
"Wonderful property!! My family and I had a great time. The location is very convenient to about everything. "
The price is AED 1,098
AED 1,992 total
includes taxes & fees
21 Sep - 22 Sep
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Crown Jewel in the Neighborhood.

8.4 out of 10, Very Good, (6)
"The house was clean, plenty of room to relax. Beds are comfortable, quiet neighborhood. "
Crown Jewel in the Neighborhood.

5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room

9.8 out of 10, Exceptional, (20)
"Place was clean and tidy. Quiet neighborhood. Well decorated."
5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room

Pleasurable Escape Hampton

9.4 out of 10, Exceptional, (19)
"The place was nice and met the needs of us. Even a late checkout which is greatly appreciated, However taking the bedding off should be apart of the cleaning fee. "
Pleasurable Escape Hampton

Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground

10.0 out of 10, Exceptional, (15)
"The house was clean and beautifully laid out to meet the needs of our group. Any issues were very, very minor and taken care of swiftly. We would definitely consider renting it out again. "
The price is AED 1,719
AED 2,600 total
includes taxes & fees
2 Sep - 3 Sep
Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground

Family fun Grotto waterfall Bethel Oasis

9.8 out of 10, Exceptional, (34)
"The property is as described. Cute and clean, we enjoyed our stay. Most importantly, the beds were comfortable which is a big deal when they are not. Would recommend this place for families. "
The price is AED 1,521
AED 2,254 total
includes taxes & fees
2 Sep - 3 Sep
Family fun Grotto waterfall Bethel Oasis

A Calm Haven in A Beautiful City

10.0 out of 10, Exceptional, (4)
"The home really felt like a home-away-from-home with everything a family would need. The home was spacious and comfortable-nestled in a quiet neighborhood-providing a much-needed reprieve from the outside hustle and bustle."
A Calm Haven in A Beautiful City

Charming Smithfield House: Walk to Downtown!

9.8 out of 10, Exceptional, (10)
"We used this home for some out of town guests to stay while they were visiting."
Charming Smithfield House: Walk to Downtown!

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

7.6 out of 10, Good, (9)
"We needed a reasonably priced home that was located near points of interest and easy to get to. The home was very roomy, a large kitchen, comfortable dining area with plenty of seating for all, large TV in the living room with plenty of comfortable seats. Three full bathrooms enough for all. "
Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning

Hot Tub | 9 beds | Fenced Yard

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. "
The price is AED 789
AED 1,907 total
includes taxes & fees
1 Sep - 2 Sep
Hot Tub | 9 beds | Fenced Yard

Inviting 3-bedroom townhome in delightful Portsmouth

8.0 out of 10, Very Good, (2)
"Quiet stay, clean and spacious. My friends and I enjoyed this stay. Short drive from most popular well traveled cities in VA also."
Inviting 3-bedroom townhome in delightful Portsmouth

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

8.8 out of 10, Excellent, (3)
"The house was perfect for our trip. It was clean and well stocked with towels and all the necessities. Lisa was very helpful and responsive to any messages we sent. Would definitely stay again!"
Family friendly in Hampton with huge yard, dog park, and 2 blocks from the bay

Historic Old Towne Southern Charm

9.6 out of 10, Exceptional, (22)
"great location and a great host I would stay again"
Historic Old Towne Southern Charm

James River Waterfront with spectacular views across the river from Williamsburg

10.0 out of 10, Exceptional, (137)
"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

Tucked away 3-bedroom estate with AC and WiFi in fabulous Hampton

6.0 out of 10, (6)
"Came to visit son whose in the Navy, stay was great nice area and shopping lots to do home was very and comfortable felt like being in your own home. Communication with own was great. "
Tucked away 3-bedroom estate with AC and WiFi in fabulous Hampton

Beachfront House on James River. Near Historic Jamestowne and Williamsburg

10.0 out of 10, Exceptional, (198)
"Great place and location "
Beachfront House on James River. Near Historic Jamestowne and Williamsburg

Perfect for families!

6.6 out of 10, (8)
"we enjoy the stay and we’ll book again great location located right behind the Newport police station. There’s also lots of things to do in the location. A big pond for fishing my family enjoyed."
The price is AED 388
AED 1,096 total
includes taxes & fees
1 Sep - 2 Sep
Perfect for families!

3 BEDROOM 2 BATH ON THE WATER

9.4 out of 10, Exceptional, (73)
"Easy access as family is close by should’ve brought our boat nice newer dock clean & neat facilities everything worked would stay here again being priced right"
3 BEDROOM 2 BATH ON THE WATER

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

9.0 out of 10, Wonderful, (16)
"House was clean and welcoming. Communication was great. I would stay again in a heart beat. I’m active duty military and host was very accommodating. "
The price is AED 415
AED 915 total
includes taxes & fees
3 Sep - 4 Sep
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

WaterFront Ground Floor - 1 BR, WiFi Smart, TV, Pet Friendly

6.0 out of 10, (1)
"Pictures were accurate for the "apartment" that was listed as a stand alone house. Playground for dogs was not fenced in by gates. Water access and pier listed was non existent. Pier/deck over water was once standing however, now all the boards are on the shoreline/beach area. Loose boards with nails piled on shoreline. Parking is TIGHT and only 4 very tight spots for vehciles. 1 parking spot is used by owner who lives upstairs of the apartments. I have pictures if needed."
WaterFront Ground Floor - 1 BR, WiFi Smart, TV, Pet Friendly
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews