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Windsor Vacation Rentals

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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 homes

Property grounds

1. 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.
The price is CA $156
CA $222 total
includes taxes & fees
Sep 11 - Sep 12
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
Smart TV, fireplace

2. 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.
The price is CA $249
CA $381 total
includes taxes & fees
Sep 10 - Sep 11
The "KINGSDALE" 2 Bedrooms
Smart TV, fireplace

3. 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
The price is CA $177
CA $305 total
includes taxes & fees
Sep 8 - Sep 9
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Exterior

4. 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.
The price is CA $277
CA $381 total
includes taxes & fees
Sep 19 - Sep 20
Cozy 3-bedroom house in charming small town Sedley
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.
The price is CA $176
CA $450 total
includes taxes & fees
Sep 14 - Sep 15
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Interior

6. Bright 3-bedroom beach house with AC in charming Norfolk

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.4 out of 10, Exceptional, (9 reviews)
The price is CA $181
CA $520 total
includes taxes & fees
Sep 8 - Sep 9
Bright 3-bedroom beach house with AC in charming Norfolk
Dining

7. Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (36 reviews)
"Great little house beach was good for small kids first trip to beach"
United States
Layton H.
The price is CA $156
CA $563 total
includes taxes & fees
Sep 24 - Sep 25
Sojourn | Coastal Cottage | 3 BR
Coffee/tea maker, fridge, microwave, oven

8. 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.
The price is CA $179
CA $485 total
includes taxes & fees
Oct 1 - Oct 2
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Iron/ironing board, WiFi (free), bed sheets

9. Hot Tub | 9 beds | Fenced Yard

Hot Tub | 9 beds | Fenced Yard
Downtown Hampton
4.8 out of 10, (8 reviews)
"Convenient location and plenty of space, but the house is in clear disrepair. We were in town to see our daughter graduate from Hampton University, and the location was ideal for the ceremony."
United States
Kristin J.
The price is CA $240
CA $763 total
includes taxes & fees
Sep 8 - Sep 9
Hot Tub | 9 beds | Fenced Yard
Dining

10. 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.
The price is CA $430
CA $933 total
includes taxes & fees
Sep 13 - Sep 14
Wooded Wonderland
Property grounds

11. 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.
The price is CA $310
CA $641 total
includes taxes & fees
Sep 8 - Sep 9
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Living area

12. 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.
The price is CA $374
CA $852 total
includes taxes & fees
Sep 12 - Sep 13
Beautiful, spacious home in welcoming Norfolk.
Coffee/tea maker, fridge, microwave, oven

13. -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.
The price is CA $552
CA $845 total
includes taxes & fees
Sep 14 - Sep 15
-NEW- Beautiful, Cozy & stylish home with office-for your family! Pet Friendly!
Exterior

14. 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.
The price is CA $450
CA $867 total
includes taxes & fees
Sep 28 - Sep 29
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Sun loungers, beach towels

15. 5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis

5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis
Hampton
9.8 out of 10, Exceptional, (42 reviews)
"So many great rooms. Loved the waterfall"
United States
Dwayne W.
The price is CA $790
CA $1,163 total
includes taxes & fees
Sep 9 - Sep 10
5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis
Interior

16. 8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
North Newport News
10.0 out of 10, Exceptional, (23 reviews)
"The nursery was great. The kitchen was well appointed. Did not care for the pans with removable handles. More comfortable living room seating would be nice. But overall a lovely home."
United States
Otis G.
The price is CA $758
CA $1,125 total
includes taxes & fees
Sep 9 - Sep 10
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
Coffee/tea maker, fridge, microwave, oven

17. 8 Miles to Busch Gardens/Spacious Family Getaway/ 7Bedroom/3 masters /5 Bath

8 Miles to Busch Gardens/Spacious Family Getaway/ 7Bedroom/3 masters /5 Bath
North Newport News
10.0 out of 10, Exceptional, (15 reviews)
"We stayed here May 14-May 17 for my daughter's William & Mary graduation. The house was beautiful and very clean and had everything we needed for our group of 10 adults. Communication with the owner was excellent and he was very helpful and very responsive with all questions. Thank you for a great stay!"
United States
Patrick K.
The price is CA $1,106
CA $1,618 total
includes taxes & fees
Sep 8 - Sep 9
8 Miles to Busch Gardens/Spacious Family Getaway/ 7Bedroom/3 masters /5 Bath
Dining

18. 1896 Historic Mansion with a general store

1896 Historic Mansion with a general store
North Newport News
9.8 out of 10, Exceptional, (10 reviews)
"Nice accommodations and nice host. Very accommodating."
United States
Jim R.
The price is CA $727
CA $1,229 total
includes taxes & fees
Sep 8 - Sep 9
1896 Historic Mansion with a general store
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

YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

10/10 Excellent
"Had every amenity needed for our stay, every staff member I spoke with was respectful and beyond helpful. Will be staying here again."
Jennifer 1-night trip
Posted 3 hours ago
YourSpace Hotels Chesapeake

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
302
Accommodation
214 Vacation Homes
Lowest Price
CA $222
Highest Price
CA $1,618

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