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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Windsor vacation rentals

A small, single-story building with a porch, a seating area with chairs and a table, and a sign that reads 'welcome home'.

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, (48 reviews)
"A great little place! Peaceful, quiet. All necessities are available."
United States
Theresa G.
The price is AED 413
AED 589 total
includes taxes & fees
29 Sep - 30 Sep
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
A two-story brick house with a front porch, a garage, and a well-maintained lawn.

2. 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, (13 reviews)
"Very nice spot to stay. The host was excellent!"
United States
Wade H.
The price is AED 661
AED 893 total
includes taxes & fees
29 Sep - 30 Sep
Cozy 3-bedroom house in charming small town Sedley
A modern kitchen with white cabinets, a built-in oven, and a dining area with a gray sofa and a table.

3. 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.
The price is AED 441
AED 1,030 total
includes taxes & fees
3 Oct - 4 Oct
Guesthouse in ideal location with private entrance
A living room with a beige sofa, a white ottoman, a patterned rug, a wooden chair, and a small table.

4. 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
8.8 out of 10, Excellent, (12 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 AED 471
AED 806 total
includes taxes & fees
29 Sep - 30 Sep
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A living room with a sectional sofa, a round ottoman, a globe on a shelf, and artwork on the walls.

5. 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.
The price is AED 430
AED 1,244 total
includes taxes & fees
3 Oct - 4 Oct
Comfortable & Private 2 Bedrm Cottage w/ King bed.
A building with a brick facade, a covered entrance with columns, and a staircase leading to the entrance.

6. Ice Ice Baby | Downtown Newport News!

Ice Ice Baby | Downtown Newport News!
Downtown Newport News
9.6 out of 10, Exceptional, (21 reviews)
"Over all stay was comfortable... and convenient! Traffic was good into Newport news... Good stay"
United States
Adria K.
Ice Ice Baby | Downtown Newport News!
A living room with a fireplace, a television, a sofa, a coffee table, and a kitchen area in the background.

7. 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 AED 661
AED 972 total
includes taxes & fees
4 Oct - 5 Oct
The "KINGSDALE" 2 Bedrooms
A modern courtyard with white furniture, a central seating area, and a small lawn.

8. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (106 reviews)
"This property was like a home away from home. Rooms were spacious and location was good. Host was very friendly."
United States
Karen
The price is AED 437
AED 502 total
includes taxes & fees
12 Oct - 13 Oct
stayAPT Suites Suffolk-Chesapeake
A narrow brick pathway flanked by two houses with siding.

9. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
The price is AED 298
AED 683 total
includes taxes & fees
29 Sep - 30 Sep
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

10. Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (9 reviews)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
The price is AED 327
AED 978 total
includes taxes & fees
20 Oct - 21 Oct
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

11. 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 AED 367
AED 1,025 total
includes taxes & fees
29 Sep - 30 Sep
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A modern kitchen with white cabinets, stainless steel appliances, a double sink, and a window with a view.

12. Spacious Portsmouth Getaway w/Game Room

Spacious Portsmouth Getaway w/Game Room
Portsmouth
7.0 out of 10, Good, (2 reviews)
"This property is in a great location near beach and also casino"
United States
JOSIE G.
The price is AED 592
AED 1,477 total
includes taxes & fees
29 Sep - 30 Sep
Spacious Portsmouth Getaway w/Game Room
A glass-top table with two cushioned chairs on a wooden deck, a vase with red flowers, and a brick wall.

13. 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, (55 reviews)
"Comfortable home and clean quiet stay. "
United States
Lisa H.
The price is AED 459
AED 983 total
includes taxes & fees
29 Sep - 30 Sep
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
A hotel room with a large bed, two bedside tables with lamps, a chair, and a window with curtains.

14. King Bed|Non-Smoking

King Bed|Non-Smoking
North Newport News
10.0 out of 10, Exceptional, (84 reviews)
"The bed was comfortable, which I really appreciated!"
United States
Anonymous traveler
The price is AED 249
AED 308 total
includes taxes & fees
29 Sep - 30 Sep
King Bed|Non-Smoking
A two-story brick building with a blue roof, a sign reading 'studio 6 extended stay,' and a parking lot with cars.

15. 1 Queen Bed|ADA/RI Shower/Smk/Kitchen

1 Queen Bed|ADA/RI Shower/Smk/Kitchen
Coliseum Central
10.0 out of 10, Exceptional, (6 reviews)
The price is AED 255
AED 302 total
includes taxes & fees
4 Oct - 5 Oct
1 Queen Bed|ADA/RI Shower/Smk/Kitchen
A multi-story building with balconies, a courtyard with seating, and a well-maintained lawn.

16. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.2 out of 10, Wonderful, (23 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is AED 437
AED 510 total
includes taxes & fees
29 Sep - 30 Sep
stayAPT Suites Hampton
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

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

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.6 out of 10, Exceptional, (13 reviews)
"The property is spacious and conveniently located near the beach and restaurants. It is family-friendly and the host is exceptionally communicative. I plan to return in the future."
United States
Sheryll
The price is AED 496
AED 1,318 total
includes taxes & fees
29 Sep - 30 Sep
Bright 3-bedroom beach house with AC in charming Norfolk
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

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

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.0 out of 10, Very good, (47 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is AED 474
AED 1,211 total
includes taxes & fees
1 Oct - 2 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
A waterfront view from a wooden deck with a white railing, a dock extending into the water, and a clear blue sky.

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

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
8.8 out of 10, Excellent, (6 reviews)
The price is AED 823
AED 1,600 total
includes taxes & fees
29 Sep - 30 Sep
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

20. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Great property not too far from the beaches! Between the pool, hot tub, mini golf, and theater room, our family had plenty to do at the house when we weren't out exploring Virginia Beach. Owner was quick to respond to any questions or needs as well."
United States
Erin W.
The price is AED 1,140
AED 2,307 total
includes taxes & fees
4 Oct - 5 Oct
Wooded Wonderland
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

Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

10/10 Excellent
"The room was nice and clean. Staff was helpful. Would stay again."
Tonia 1-night trip
Posted 2 hours ago
Wyndham Garden Norfolk Downtown

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?

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home: Visitors like this Windsor vacation home rental. It is located in the city center and offers a selection of games, air-conditioning, and laundry facilities 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 Windsor Castle Park 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.