Book Holiday Homes in Isle of Wight

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Isle of Wight

Luxe Lakefront Portsmouth Home: Fish, Swim & Play!

Luxe Lakefront Portsmouth Home: Fish, Swim & Play!

2 out of 5
Portsmouth
With a stay at this vacation home in Portsmouth, you'll be on the waterfront, within a 15-minute drive of Waterside District and Rivers Casino Portsmouth.
Luxe Lakefront Portsmouth Home: Fish, Swim & Play!
Private Estate on 4 Acres

Private Estate on 4 Acres

Portsmouth
With a stay at this vacation home in Portsmouth, you'll be on a lake, within a 15-minute drive of Waterside District and Sentara BelleHarbour.
Private Estate on 4 Acres
The Great Gatsby: Pink Flamingo Lounge Retreat!

The Great Gatsby: Pink Flamingo Lounge Retreat!

2 out of 5
Spring Grove
Located in Spring Grove, this vacation home is in a rural location, within a 15-minute drive of Smith's Fort and Chippokes Plantation State Park.
The Great Gatsby: Pink Flamingo Lounge Retreat!
Save an average of 15% on thousands of hotels when you're signed in
Charming Smithfield House: Walk to Downtown!

Charming Smithfield House: Walk to Downtown!

Smithfield
Located in Smithfield, this vacation home is by the sea, within a 5-minute drive of Windsor Castle Park and Isle of Wight County Museum.
Charming Smithfield House: Walk to Downtown!
Uncle Bill's Lodge & Soccer Pool Showdown

Uncle Bill's Lodge & Soccer Pool Showdown

Surry
Located in Spring Grove, this vacation home is in a rural location, within a 15-minute drive of Smith's Fort and Chippokes Plantation State Park.
Uncle Bill's Lodge & Soccer Pool Showdown
Wooded Wonderland

Wooded Wonderland

Portsmouth
With a stay at this vacation home in Portsmouth, you'll be within a 15-minute drive of Waterside District and Old Dominion University.
Wooded Wonderland
History, Art, Nature. Built  in 1760, 110 Acres of Ancient Woodland Preserve

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

Surry
Located in Spring Grove, this vacation home is in a rural location, within a 15-minute drive of Smith's Fort and Chippokes Plantation State Park.
History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve
The Cracker Jack House: A Military Salute & Arcade!

The Cracker Jack House: A Military Salute & Arcade!

Surry
Located in Surry, this vacation home is in a rural location, within a 15-minute drive of Chippokes Plantation State Park and Smith's Fort.
The Cracker Jack House: A Military Salute & Arcade!
Beachfront House on James River.  Near Historic Jamestowne and Williamsburg

Beachfront House on James River. Near Historic Jamestowne and Williamsburg

Surry
Located in Surry, this vacation home is on the waterfront, within a 10-minute drive of Chippokes Plantation State Park and Smith's Fort.
Beachfront House on James River. Near Historic Jamestowne and Williamsburg
Don't see what you're looking for?
See all available properties in Isle of Wight
View all properties
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.

Isle of Wight Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Isle of Wight vacation homes are the perfect way for you to wing it.

Holiday houses in Isle of Wight let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Isle of Wight in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Isle of Wight adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Isle of Wight with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Isle of Wight vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Isle of Wight Holiday Homes essential information

Accommodation
77 Holiday Homes
Lowest Price
AU$141
Highest Price
AU$174
Popular accommodation
Luxe Lakefront Portsmouth Home: Fish, Swim & Play!, Private Estate on 4 Acres, The Great Gatsby: Pink Flamingo Lounge Retreat!, Charming Smithfield House: Walk to Downtown!, Uncle Bill's Lodge & Soccer Pool Showdown, Wooded Wonderland, History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve, The Cracker Jack House: A Military Salute & Arcade!, Beachfront House on James River. Near Historic Jamestowne and Williamsburg

Top trending hotels in Isle of Wight

Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
12570 Jefferson Ave, Newport News, VA
Fully refundableReserve now, pay when you stay
The price is AU$154 per night from 2 Mar to 3 Mar
AU$154
includes taxes & fees
2 Mar - 3 Mar
With a stay at Comfort Suites Airport in Newport News (Central Newport News), you'll be within a 10-minute drive of Fort Eustis and Christopher Newport ...
Comfort Suites Airport
Comfort Inn Newport News - Hampton I-64

Comfort Inn Newport News - Hampton I-64

2.5 out of 5
12330 Jefferson Ave, Newport News, VA
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 25 Feb to 26 Feb
AU$141
includes taxes & fees
25 Feb - 26 Feb
With a stay at Comfort Inn Newport News - Hampton I-64 in Newport News (Central Newport News), you'll be within a 15-minute drive of Christopher Newport University ...
Comfort Inn Newport News - Hampton I-64
Courtyard by Marriott Newport News Airport

Courtyard by Marriott Newport News Airport

3 out of 5
530 Saint Johns Road, Newport News, VA
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 2 Mar to 3 Mar
AU$169
includes taxes & fees
2 Mar - 3 Mar
With a stay at Courtyard by Marriott Newport News Airport, you'll be centrally located in Newport News, within a 10-minute drive of Christopher Newport University ...
Courtyard by Marriott Newport News Airport
Save an average of 15% on thousands of hotels when you're signed in
Springhill Suites by Marriott Hampton Coliseum

Springhill Suites by Marriott Hampton Coliseum

3 out of 5
1997 Power Plant Highway, Hampton, VA
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 2 Mar to 3 Mar
AU$174
includes taxes & fees
2 Mar - 3 Mar
With a stay at Springhill Suites by Marriott Hampton Coliseum, you'll be centrally located in Hampton, a 3-minute drive from Hampton Coliseum and 7 minutes from ...
Springhill Suites by Marriott Hampton Coliseum
Don't see what you're looking for?
See all available properties in Isle of Wight
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.