Windsor Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Windsor vacation rentals

Dining

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
9.6 out of 10, Exceptional, (4 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 ￥12,591
￥41,343 total
includes taxes & fees
May 14 - May 15
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Fridge, microwave, oven, stovetop

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, (27 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 ￥16,662
￥46,567 total
includes taxes & fees
May 20 - May 21
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Property grounds

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, (45 reviews)
"Beautiful place, beautiful location "
United States
rocco m.
The price is ￥18,863
￥41,689 total
includes taxes & fees
May 18 - May 19
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Property grounds

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
The price is ￥12,732
￥29,213 total
includes taxes & fees
May 18 - May 19
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Dining

Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (34 reviews)
"The house was clean and had everything you need. The neighborhood was quiet. Beach access was just a short walk away and not crowded. "
United States
Daniel P.
The price is ￥20,835
￥67,513 total
includes taxes & fees
May 20 - May 21
Sojourn | Coastal Cottage | 3 BR
Apartment | Private kitchen

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is ￥21,323
￥46,451 total
includes taxes & fees
May 14 - May 15
The Speakeasy Downtown Newport News
Interior

❤️The Safe House❤️Downtown Newport News!

❤️The Safe House❤️Downtown Newport News!
Downtown Newport News
8.8 out of 10, Excellent, (11 reviews)
"Quiet and a very cute posh spot. Everything was absolutely beautiful."
United States
chevon
The price is ￥15,020
￥37,978 total
includes taxes & fees
May 14 - May 15
❤️The Safe House❤️Downtown Newport News!
Smart TV, fireplace

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
9.6 out of 10, Exceptional, (4 reviews)
"It’s was great staying "
United States
Shalena K.
The price is ￥22,064
￥37,265 total
includes taxes & fees
May 17 - May 18
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Smart TV

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay,host was very hospital.love to enjoy it again in December "
United States
earnest d.
The price is ￥21,221
￥58,500 total
includes taxes & fees
May 14 - May 15
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
Interior

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.4 out of 10, Exceptional, (19 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is ￥17,291
￥51,448 total
includes taxes & fees
May 27 - May 28
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Interior

Large 2 bedroom | Queen beds | Safe Area

Large 2 bedroom | Queen beds | Safe Area
Wythe
7.8 out of 10, Good, (10 reviews)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is ￥19,018
￥44,876 total
includes taxes & fees
May 18 - May 19
Large 2 bedroom | Queen beds | Safe Area
Fridge, microwave, oven, stovetop

4 Bedroom Cottage - 5 Minutes from both beaches

4 Bedroom Cottage - 5 Minutes from both beaches
Hampton
9.4 out of 10, Exceptional, (29 reviews)
"The host was very accommodating. Our family had an emergency and we needed a place to stay in close proximity to the hospital. Although this listing said no pets, she allowed us to bring our pets. We are so appreciative. The house was beautiful and very clean. Thank you for our stay."
United States
Ty V.
The price is ￥34,236
￥85,059 total
includes taxes & fees
May 14 - May 15
4 Bedroom Cottage - 5 Minutes from both beaches
Interior

❤️Ice Ice Baby❤️Downtown Newport News!

❤️Ice Ice Baby❤️Downtown Newport News!
Downtown Newport News
9.4 out of 10, Exceptional, (19 reviews)
"We had a great trip. Loved the industrial look and feel of the apartment. The bed was super comfy and the location was great. It was so convenient to go to the restaurants a few doors down. "
United States
Linda B.
The price is ￥15,350
￥38,521 total
includes taxes & fees
May 14 - May 15
❤️Ice Ice Baby❤️Downtown Newport News!
Property grounds

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, (43 reviews)
"Love the place!"
United States
Sheila P.
The price is ￥17,684
￥25,212 total
includes taxes & fees
May 21 - May 22
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
Marina

Your Tropical Oasis awaits in Hampton Roads Virginia

Your Tropical Oasis awaits in Hampton Roads Virginia
Portsmouth
The price is ￥31,438
￥51,448 total
includes taxes & fees
May 15 - May 16
Your Tropical Oasis awaits in Hampton Roads Virginia
Apartment | 2 bedrooms

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
7.4 out of 10, Good, (3 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is ￥20,869
￥45,912 total
includes taxes & fees
May 14 - May 15
Ice Ice Baby Downtown Newport News
TV

Perfect for families!

Perfect for families!
Hudson Terrace
6.8 out of 10, (11 reviews)
"Great location for a family trip"
United States
Justin R.
The price is ￥30,327
￥61,859 total
includes taxes & fees
May 18 - May 19
Perfect for families!
Golf

Luxury Riverfront Condo w/ sunrise & sunset views

Luxury Riverfront Condo w/ sunrise & sunset views
Kingsmill
9.6 out of 10, Exceptional, (76 reviews)
"Lovely view of river and the woods. Marina has nice view of river and tasty food. Also like that it’s close to Jamestown and Downtown Williamsburg."
United States
Jeffrey
The price is ￥26,738
￥54,732 total
includes taxes & fees
May 21 - May 22
Luxury Riverfront Condo w/ sunrise & sunset views
Exterior

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, (42 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is ￥47,393
￥92,417 total
includes taxes & fees
May 19 - May 20
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Private kitchen

The Magnolia JEM With A Private Entrance

The Magnolia JEM With A Private Entrance
Suffolk
The price is ￥19,649
￥40,656 total
includes taxes & fees
Jun 12 - Jun 13
The Magnolia JEM With A Private Entrance
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

Quality Inn & Suites Olde Town

Quality Inn & Suites Olde Town

8/10 Good
"Room was clean and comfortable. Towels are pretty flimsy. They need to be replaced. Bath tile could use a little bleach to whiten up the caulk in some areas. Otherwise, the place as clean. They even mopped the floors before we checked in."
Joseph 1-night trip
Posted 2 hours ago
Quality Inn & Suites Olde Town

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windsor!

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?

Cozy 4 Bed 2 Bath Home - Norfolk, Centrally Located: Visitors like this Windsor vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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 Chesapeake Square Mall and Lake Meade 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.