Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.8 out of 10, Exceptional, (17 reviews)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
The price is ¥15,740
¥46,044 total
includes taxes & fees
Feb 16 - Feb 17
Comfortable & Private 2 Bedrm Cottage w/ King bed.

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (60 reviews)
"The staff was so friendly. The rooms were so nice. I loved the kitchen and breakfast bar."
United States
Nicole
The price is ¥16,353
¥18,798 total
includes taxes & fees
Feb 15 - Feb 16
stayAPT Suites Suffolk-Chesapeake

❤️The Safe House❤️Downtown Newport News!

❤️The Safe House❤️Downtown Newport News!
Downtown Newport News
8.8 out of 10, Excellent, (10 reviews)
"Quiet and a very cute posh spot. Everything was absolutely beautiful."
United States
chevon
The price is ¥12,789
¥34,477 total
includes taxes & fees
Feb 12 - Feb 13
❤️The Safe House❤️Downtown Newport News!

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 ¥17,957
¥63,028 total
includes taxes & fees
Mar 2 - Mar 3
Sojourn | Coastal Cottage | 3 BR

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 ¥12,515
¥28,715 total
includes taxes & fees
Feb 24 - Feb 25
Private 1 Bed Apt - Historic Olde Towne Portsmouth

Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning

Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning
Willoughby Spit
9.0 out of 10, Wonderful, (7 reviews)
"Would return again!"
United States
Parker L.
Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning

Water Front Delight on the Bay

Water Front Delight on the Bay
Willoughby Spit
7.8 out of 10, Good, (25 reviews)
"Everything was very nice really enjoyed "
United States
Deborah B.
The price is ¥15,459
¥55,418 total
includes taxes & fees
Feb 28 - Mar 1
Water Front Delight on the Bay

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, (36 reviews)
"Old solid brick building. Don't build them like that anymore! Clean, quiet, comfortable. Great choice of restaurants close by and ferry service across river to Norfolk. Had a Great time "
United States
Daniel C.
The price is ¥16,996
¥39,023 total
includes taxes & fees
Feb 24 - Feb 25
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is ¥14,718
¥38,516 total
includes taxes & fees
Feb 12 - Feb 13
The Speakeasy Downtown Newport News

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 ¥18,382
¥44,428 total
includes taxes & fees
Feb 12 - Feb 13
Large 2 bedroom | Queen beds | Safe Area

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
8.0 out of 10, Very Good, (1 review)
"Host is communicative and relaxed (not trying to micromanage your stay). I forgot to check the pics and descriptions for a microwave but there isn’t one. Alternatively, there is a hot plate and a pot. I gave 4 out of 5 stars due to the coffeemaker not working and having one washcloth for two people but it was pleasant other than that. "
United States
Courtney R.
The price is ¥12,515
¥23,740 total
includes taxes & fees
Feb 24 - Feb 25
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
9.0 out of 10, Wonderful, (39 reviews)
"It was amazing. The house is dope, I highly recommend this house to anyone and I will be staying there again in the future!"
United States
Varstine S.
The price is ¥19,932
¥53,947 total
includes taxes & fees
Feb 24 - Feb 25
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

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, (25 reviews)
"The place was noce and quiet. "
United States
Tomar B.
The price is ¥15,451
¥44,530 total
includes taxes & fees
Feb 24 - Feb 25
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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)
"Wonderful stay. This is a very cute and comfortable place. Will stay here again. "
United States
Denise P.
The price is ¥17,382
¥24,781 total
includes taxes & fees
Feb 15 - Feb 16
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

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 ¥20,859
¥52,704 total
includes taxes & fees
Feb 24 - Feb 25
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

The Magnolia JEM With A Private Entrance

The Magnolia JEM With A Private Entrance
Suffolk
The price is ¥15,615
¥35,048 total
includes taxes & fees
Feb 12 - Feb 13
The Magnolia JEM With A Private Entrance

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is ¥41,067
¥96,572 total
includes taxes & fees
Feb 28 - Mar 1
Centrally Located Hampton Roads Home w/ Game Room!

Luxury Riverfront Condo w/ sunrise & sunset views

Luxury Riverfront Condo w/ sunrise & sunset views
Kingsmill
9.6 out of 10, Exceptional, (73 reviews)
"Great location, easy process"
United States
Dylan G.
The price is ¥26,282
¥53,799 total
includes taxes & fees
Feb 24 - Feb 25
Luxury Riverfront Condo w/ sunrise & sunset views

THE"HAVEN" (1 BEDROOM)

THE"HAVEN" (1 BEDROOM)
Franklin
9.6 out of 10, Exceptional, (7 reviews)
"Every time we stay it is very clean, well stocked, easy to enter and very quiet. "
United States
Neomia L.
The price is ¥18,972
¥34,267 total
includes taxes & fees
Feb 12 - Feb 13
THE"HAVEN" (1 BEDROOM)

The "KINGSDALE" 2 Bedrooms

The "KINGSDALE" 2 Bedrooms
Franklin
10.0 out of 10, Exceptional, (8 reviews)
"Nice place.Was clean and we had everything we needed. "
United States
Terri G.
The price is ¥27,812
¥42,721 total
includes taxes & fees
Feb 17 - Feb 18
The "KINGSDALE" 2 Bedrooms
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

Find out more about Windsor

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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?

5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room : Visitors like this Windsor vacation home rental. It is located next to a golf course and has a patio, a garden, and a barbecue grill to put you at ease 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Planters Peanut Center and Suffolk Seaboard Station Railroad Museum.

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.