Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

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 ¥12,374
¥28,392 total
includes taxes & fees
Feb 24 - Feb 25
Private 1 Bed Apt - Historic Olde Towne Portsmouth

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 ¥15,171
¥54,385 total
includes taxes & fees
Feb 28 - Mar 1
Water Front Delight on the Bay

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
10.0 out of 10, Exceptional, (2 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is ¥15,888
¥41,019 total
includes taxes & fees
Feb 15 - Feb 16
Ice Ice Baby Downtown Newport News

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (61 reviews)
"The staff was so friendly. The rooms were so nice. I loved the kitchen and breakfast bar."
United States
Nicole
The price is ¥17,999
¥20,671 total
includes taxes & fees
Mar 1 - Mar 2
stayAPT Suites Suffolk-Chesapeake

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 ¥15,277
¥44,028 total
includes taxes & fees
Feb 26 - Feb 27
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Shipside Suite~Modern~ Fast WI-FI~Cozy

Shipside Suite~Modern~ Fast WI-FI~Cozy
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"Very good communication with the host Area was quiet. Rental very clean & well stocked. Was a very enjoyable stay! "
United States
Rheta P.
The price is ¥17,110
¥51,123 total
includes taxes & fees
Feb 26 - Feb 27
Shipside Suite~Modern~ Fast WI-FI~Cozy

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 ¥12,374
¥23,473 total
includes taxes & fees
Feb 26 - Feb 27
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

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 ¥16,805
¥38,233 total
includes taxes & fees
Feb 19 - Feb 20
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

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 ¥15,447
¥45,186 total
includes taxes & fees
Feb 16 - Feb 17
Comfortable & Private 2 Bedrm Cottage w/ King bed.

❤️Ice Ice Baby❤️Downtown Newport News!

❤️Ice Ice Baby❤️Downtown Newport News!
Downtown Newport News
9.4 out of 10, Exceptional, (19 reviews)
"Was able to cook and relax for little getaway. "
United States
Rebecca S.
The price is ¥14,116
¥36,028 total
includes taxes & fees
Feb 15 - Feb 16
❤️Ice Ice Baby❤️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 ¥16,703
¥42,440 total
includes taxes & fees
Feb 17 - Feb 18
Large 2 bedroom | Queen beds | Safe Area

Perfect for families!

Perfect for families!
Hudson Terrace
6.6 out of 10, (10 reviews)
"Great location for a family trip"
United States
Justin R.
The price is ¥18,151
¥47,918 total
includes taxes & fees
Feb 26 - Feb 27
Perfect for families!

Spacious Downtown Apartment w/patio.

Spacious Downtown Apartment w/patio.
Downtown Norfolk
The price is ¥15,277
¥29,448 total
includes taxes & fees
Mar 16 - Mar 17
Spacious Downtown Apartment w/patio.

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 ¥17,187
¥24,503 total
includes taxes & fees
Feb 15 - Feb 16
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is ¥40,179
¥94,483 total
includes taxes & fees
Feb 28 - Mar 1
Centrally Located Hampton Roads Home w/ Game Room!

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 ¥18,619
¥33,804 total
includes taxes & fees
Feb 14 - Feb 15
THE"HAVEN" (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 ¥20,624
¥52,110 total
includes taxes & fees
Feb 26 - Feb 27
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

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 ¥19,402
¥64,776 total
includes taxes & fees
Mar 1 - Mar 2
Sojourn | Coastal Cottage | 3 BR

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 ¥27,499
¥42,240 total
includes taxes & fees
Feb 17 - Feb 18
The "KINGSDALE" 2 Bedrooms

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

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Willoughby Spit
7.8 out of 10, Good, (12 reviews)
"Loved the view and communication with owner was exceptional. "
United States
Dottie H.
The price is ¥38,040
¥76,179 total
includes taxes & fees
Feb 25 - Feb 26
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
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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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 Carrollton Nike 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.