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Compare 75 Vacation Homes in Isle of Wight with updated reviews, rates, and availability.

Luxe Lakefront Portsmouth Home: Fish, Swim & Play!

2.0 star property
9.4 out of 10, Exceptional, (3)
"Well appointed home with beautiful waterfront grounds. Very comfortable get away, convenient to Norfolk and Virginia Beach areas."
Luxe Lakefront Portsmouth Home: Fish, Swim & Play!

Private Estate on 4 Acres

9.2 out of 10, Wonderful, (28)
"This house was perfect for our extended family vacation. The house is very old but the owners made a lot very nice improvements. You can tell there are more things to do though. Communication was not that great but they were very nice when we did hear from them. Super easy check in"
Private Estate on 4 Acres

The Great Gatsby: Pink Flamingo Lounge Retreat!

2.0 star property
8.8 out of 10, Excellent, (3)
"The property was clean and well-maintained, and in a convenient location near Williamsburg, Smithfield and other historic locations. Access to the Jamestowne-Scotland ferry was great."
The Great Gatsby: Pink Flamingo Lounge Retreat!

Charming Smithfield House: Walk to Downtown!

10.0 out of 10, Exceptional, (4)
"Visited for son’s wedding. Wonderful location, amazing hosts. Everyone was so kind and welcoming. Home is beautiful and has everything you need. Definitely will be booking again!"
Charming Smithfield House: Walk to Downtown!

Uncle Bill's Lodge & Soccer Pool Showdown

8.4 out of 10, Very Good, (7)
"Perfectly clean and comfortable but no privacy. Pet friendly but neighbor allowed their dog to come to fenced yard at all hours which made my 1 dog bark. Not sure if neighbor was owner. Great fenced yard but as I stated, no privacy. Homes close by even in backyard. Fine for families who want to visit from out of town visiting Busch Gardens/Water Country and CW as backyard is entertaining and home is affordable. Just not what we were looking for. Photos and description made us feel it would be...
Uncle Bill's Lodge & Soccer Pool Showdown

Wooded Wonderland

9.6 out of 10, Exceptional, (9)
"As described in the listing but roomier and well-appointed. Loved the mini golf in the back—our 7 1/2 yo grandson played 3 times during our 2 night stay!"
The price is AED 716
AED 1,772 total
includes taxes & fees
3 Feb - 4 Feb
Wooded Wonderland

History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

10.0 out of 10, Exceptional, (129)
"Wonderful old-world house in gorgeous woodlands, close to historic sites and riverside walks. We loved it."
History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

The Cracker Jack House: A Military Salute & Arcade!

9.4 out of 10, Exceptional, (9)
"The house is just as shown in the pictures. I was a little disappointed that there was no Ms Pacman video game, but that didn't ruin our stay. Communication was excellent. I would recommend this house to others. "
The Cracker Jack House: A Military Salute & Arcade!

Beachfront House on James River. Near Historic Jamestowne and Williamsburg

10.0 out of 10, Exceptional, (191)
"The house was spotless and the hosts answered any questions we had right away! The kitchen was well stocked and beds were comfortable. Such a beautiful view from this spot! We enjoyed our time here very much."
Beachfront House on James River. Near Historic Jamestowne and Williamsburg

Hilton Village Home

9.6 out of 10, Exceptional, (30)
"Overall, the place needed. All complaints we had were was not well lite on the side of the house where you entered. Stairs to the second floor are tricky to someone who has a disability."
The price is AED 569
AED 1,060 total
includes taxes & fees
31 Jan - 1 Feb
Hilton Village Home

James River Waterfront with spectacular views across the river from Williamsburg

10.0 out of 10, Exceptional, (131)
"Beautiful immaculate home with stunning views of the James River. We visited Williamsburg each day via the ferry. Great communication with the owner. This was our second time staying here. Highly recommend!"
James River Waterfront with spectacular views across the river from Williamsburg

Historic Gem in the Heart of Hilton Village on the James River

9.6 out of 10, Exceptional, (33)
"Excellent "
The price is AED 643
AED 1,165 total
includes taxes & fees
10 Feb - 11 Feb
Historic Gem in the Heart of Hilton Village on the James River

Cheerful 2 bedroom 2 full bathroom townhouse

10.0 out of 10, Exceptional, (7)
"Clean cozy and comfortable, my family and I were very much comfortable with all the ammeneties provided. Looking forward to another stay in the future. "
Cheerful 2 bedroom 2 full bathroom townhouse

Lakefront Newport News Home, 6 Mi to City Center!

2.0 star property
8.0 out of 10, Very Good, (4)
"This rental was the perfect size abcs location for our family to enjoy Thanksgiving together. Our property manager was very accommodating, letting me do an early check in. The TV in the upstairs master didn’t work, and the WiFi was disconnected. "
Lakefront Newport News Home, 6 Mi to City Center!

Charming Hampton Home w/ Fireplace, Deck & Grill!

10.0 out of 10, Exceptional, (7)
"Great location. Very clean. "
Charming Hampton Home w/ Fireplace, Deck & Grill!

Experience Chesapeake Your Way and Relax with Golf Entire home

8.2 out of 10, Very Good, (11)
"My family (husband, children 12 & 18) and I stayed at this property in Aug 2024, while visiting family and the amusement parks. We enjoyed the property. Location was safe and comfortable. Perfect distance from Busch Gardens, Water Country USA, and Virginia Beach. Bathrooms could use updating. Beds were overall comfortable. Reasonably priced. "
The price is AED 720
AED 1,072 total
includes taxes & fees
2 Feb - 3 Feb
Experience Chesapeake Your Way and Relax with Golf Entire home

Spacious Chesapeake Home w/ Pool Table!

8.6 out of 10, Excellent, (4)
"Very nice location. Great host very freindly and great communication. House was very clean and had no issues on multiple stays"
Spacious Chesapeake Home w/ Pool Table!

Charming Hampton Home ~ 7 Mi to Buckroe Beach!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Some friends and I stayed so that we could attend an event at the Hampton Coliseum. The house was great and very accommodating!"
Charming Hampton Home ~ 7 Mi to Buckroe Beach!

Hidden Gem spacious 4bedroom home away from home

Hidden Gem spacious 4bedroom home away from home

Next to CNU! | New Listing with Beautiful Finishes

9.0 out of 10, Wonderful, (14)
"Hi! This location was perfect for a friends weekend away visiting some of our kids at CNU. Super close to campus and everything Newport News has to offer. Only issue was the location of the driveway, it was kinda deceiving when you pulled up. Everythingelse was perfect"
Next to CNU! | New Listing with Beautiful Finishes
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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Other property types in Isle of Wight

stayAPT Suites Suffolk-Chesapeake

2.5 star property
The price is AED 437
AED 502 total
includes taxes & fees
3 Feb - 4 Feb
stayAPT Suites Suffolk-Chesapeake

Private Estate on 4 Acres

9.2 out of 10, Wonderful, (28)
"This house was perfect for our extended family vacation. The house is very old but the owners made a lot very nice improvements. You can tell there are more things to do though. Communication was not that great but they were very nice when we did hear from them. Super easy check in"
Private Estate on 4 Acres

Luxe Lakefront Portsmouth Home: Fish, Swim & Play!

2.0 star property
9.4 out of 10, Exceptional, (3)
"Well appointed home with beautiful waterfront grounds. Very comfortable get away, convenient to Norfolk and Virginia Beach areas."
Luxe Lakefront Portsmouth Home: Fish, Swim & Play!
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.