Isle of Wight Holiday Rentals

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Holiday Rentals in Isle of Wight

Hilton Village Home

9.6 out of 10, Exceptional, (28)
"This place was so great to stay at!"
The price is NZ$504
includes taxes & fees
30 Nov - 1 Dec
Hilton Village Home

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"
The price is NZ$2,255
includes taxes & fees
3 Dec - 4 Dec
Private Estate on 4 Acres

Uncle Bill's Lodge & Soccer Pool Showdown

9.4 out of 10, Exceptional, (6)
"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

Beautiful 4bedroom vacation pool home, where relaxation & indulgence intertwine.

10.0 out of 10, Exceptional, (25)
"The house looked exactly like the pictures we ran into a few problems but not with the host or the house we enjoyed our stay and it was pretty close to our homecoming I would definitely recommend, house was extremely clean "
Beautiful 4bedroom vacation pool home, where relaxation & indulgence intertwine.

Colonial Smithfield Basement Apartment- close to Williamsburg, VA beach, & more

10.0 out of 10, Exceptional, (1)
"The stay started out so well with messages from my host, and it was such a beautiful place. I spent a lot of time sleeping in because of the comfy bed, I toyed around in the kitchen, and spent time in the backyard for reflection. The location is perfect, and I didn’t need to drive. It was the best stay I’ve ever had."
The price is NZ$438
includes taxes & fees
2 Dec - 3 Dec
Colonial Smithfield Basement Apartment- close to Williamsburg, VA beach, & more

James River Waterfront with spectacular views across the river from Williamsburg

10.0 out of 10, Exceptional, (127)
"Our family has stayed at a number of VRBO's in this general price range, and we were fairly pleased with each of them. This one was a step above the others. Everything was exactly as advertised. The house is big and as nice as the pictures indicate. Everything was well-maintained and very clean. The surrounding area is beautiful. There were no surprises. Everything that you would expect to work, worked great. Communication was prompt and very clear. The nearby ferry is very well run and...
James River Waterfront with spectacular views across the river from Williamsburg

Experience Chesapeake Your Way and Relax with Golf Entire home

8.8 out of 10, Excellent, (9)
"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 NZ$471
includes taxes & fees
25 Nov - 26 Nov
Experience Chesapeake Your Way and Relax with Golf Entire home

Fun Family and Pet Friendly 3 Bedroom Home Close to Everything

10.0 out of 10, Exceptional, (4)
"We are a first time VRBO customer, and were looking for a home near our daughter’s college so the family could visit during a long weekend. The host was very responsive and kept a nice place with plenty of amenities that kept our family busy and happy. The large fenced-in yard was great for our dogs. We will return! "
The price is NZ$672
includes taxes & fees
25 Nov - 26 Nov
Fun Family and Pet Friendly 3 Bedroom Home Close to Everything

Wooded Wonderland

9.6 out of 10, Exceptional, (7)
"Great property. Pool, hot tub and a very challenging mini putt-putt course. Furniture is in good shape and comfortable. One of the bedrooms has an adjustable bed ( same model as I have at home) so that was a very nice and welcomed surprise. We have ongoing business in the area so looking forward to staying here in the future. "
The price is NZ$772
includes taxes & fees
25 Nov - 26 Nov
Wooded Wonderland

The Cracker Jack House: A Military Salute & Arcade!

9.4 out of 10, Exceptional, (8)
"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!

Next to CNU! | New Listing with Beautiful Finishes

9.4 out of 10, Exceptional, (9)
"Carl was great with proactive communication. The house was exactly like the pictures. There were special little extras like coffee, toiletries, plenty of TV channels with sports, and household supplies. Very conveniently located near stores and restaurants. Pleasant little neighborhood with great parking. Thank you for making our time together so special. We highly recommend and would absolutely come again. "
The price is NZ$878
includes taxes & fees
25 Nov - 26 Nov
Next to CNU! | New Listing with Beautiful Finishes

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

10.0 out of 10, Exceptional, (124)
"Outstanding property! A place one can relax and enjoy the beautiful surroundings. Conveniently located to ferry’s. The small town of Surry has friendly people. I highly recommend a visit to this property."
History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

Bright Chesapeake Home Near Shopping & Dining

10.0 out of 10, Exceptional, (3)
"The property was exactly what my family needed while we were in town for the softball world series. Clean and comfortable! My husband spoke to the owners and they were very pleasant. Will stay again should we find ourselves in the area."
Bright Chesapeake Home Near Shopping & Dining

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!

❤️The Speakeasy❤️Downtown Newport News!

8.0 out of 10, Very good, (7)
"Close to highway to get to everything quickly, great coffee shop, pizzeria and bar on 1st floor, brewery and distillery right next door. Clean place and great communication with owner. Will definitely rent again when i come back to Newport News!!"
The price is NZ$392
includes taxes & fees
25 Nov - 26 Nov
❤️The Speakeasy❤️Downtown Newport News!

Beautiful fully renovated two bedroom condo

6.0 out of 10, (2)
"Overall stay was good! Communication with property owner was good. Easy fast check in. The condo was a little dirty, shower tub in master dirty, stained, and some soap scum buildup. Didn’t provide enough towels or washcloths for number of people or nights. Never found any extra blankets or pillows. The smoke detector was chirping when we arrived had to replace the battery twice during our stay. The condo had a bad smell (thinking it was neighbors up above). Location was great and central to...
The price is NZ$678
includes taxes & fees
25 Nov - 26 Nov
Beautiful fully renovated two bedroom condo

Charming Smithfield House: Walk to Downtown!

10.0 out of 10, Exceptional, (3)
"We used this home for some out of town guests to stay while they were visiting."
Charming Smithfield House: Walk to Downtown!

Centrally Located Hampton Home: 6 Mi to Downtown!

9.6 out of 10, Exceptional, (8)
"This house accommodated our group nicely, even considering a single bathroom for 4 bedrooms. Very clean, comfortable beds and bedding, and several places for groups to gather and relax. A couple of quirks that were not a problem, such as the open-concept bathroom in the master. Hopefully the owner invests in adequate flatware and dishes for a large group. The location was great - 10 minutes or less to CNU and other destinations."
Centrally Located Hampton Home: 6 Mi to Downtown!

Delightful 1 Bedroom RV Near Ft. Eustis

9.0 out of 10, Wonderful, (2)
"We hadn’t stayed in an RV before, so this was a unique experience for us. Very clean & cozy accommodations and located close to many tourist attractions in the surrounding area. Easy parking out front was helpful, and the detailed & friendly communication with the host was also appreciated."
Delightful 1 Bedroom RV Near Ft. Eustis

Beachfront House on James River. Near Historic Jamestowne and Williamsburg

10.0 out of 10, Exceptional, (189)
"We enjoyed all that Linda and A.C. provided. Above and beyond our expectations "
Beachfront House on James River. Near Historic Jamestowne and Williamsburg
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 types of properties in Isle of Wight you may be interested in

Comfort Inn Newport News - Hampton I-64

2.5 star property
8.4 out of 10, Very good, (1077)
"Good quality stay"
The price is NZ$147
includes taxes & fees
18 Dec - 19 Dec
Comfort Inn Newport News - Hampton I-64

Comfort Suites Airport

2.5 star property
8.6 out of 10, Excellent, (1002)
"In a area where everything is in walking distance"
The price is NZ$158
includes taxes & fees
8 Dec - 9 Dec
Comfort Suites Airport

Days Inn by Wyndham Newport News City Center Oyster Point

2.0 star property
6.0 out of 10, (1053)
"Thank you "
The price is NZ$112
includes taxes & fees
26 Nov - 27 Nov
Days Inn by Wyndham Newport News City Center Oyster Point
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Isle of Wight?

Yes, there are holiday rentals close to the most popular sights in Isle of Wight, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Isle of Wight has to offer?

Hilton Village Home: This holiday home rental outside of Isle of Wight offers a fireplace, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Isle of Wight?

Explore the area and cultural attractions such as Boykin's Tavern, or visit one of the family-friendly sights such as Mariner's Museum. Huntington Beach and Christopher Newport University are a couple of places you'll find in the wider area.

What are holiday rentals like in Isle of Wight?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Isle of Wight. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip.