Book Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Portsmouth
The price is AU$648 per night from 7 Apr to 8 Apr
AU$648
includes taxes & fees
7 Apr - 8 Apr
With a stay at this vacation home, you'll be centrally located in Portsmouth, within a 10-minute drive of Waterside District and Old Dominion University.
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
NEW! Big Waterfront House w/ Amazing View and Swim Deck

NEW! Big Waterfront House w/ Amazing View and Swim Deck

1449 Bayville Street, Willoughby Spit, Norfolk, VA
With a stay at this vacation home in Norfolk (Willoughby Spit), you'll be within a 15-minute drive of Naval Station Norfolk and Hampton University.
NEW! Big Waterfront House w/ Amazing View and Swim Deck
Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR

Norfolk
The price is AU$558 per night from 9 Apr to 10 Apr
AU$558
includes taxes & fees
9 Apr - 10 Apr
With a stay at this vacation home in Norfolk (Willoughby Spit), you'll be within a 15-minute drive of Naval Station Norfolk and Hampton University.
Sojourn | Coastal Cottage | 3 BR
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Charming 4-bedroom bungalow with AC and WiFi in Hampton, with washer and dryer.

Charming 4-bedroom bungalow with AC and WiFi in Hampton, with washer and dryer.

Hampton
With a stay at this vacation home in Hampton (Aberdeen Gardens), you'll be a 4-minute drive from Hampton Coliseum and 8 minutes from Langley Air Force Base.
Charming 4-bedroom bungalow with AC and WiFi in Hampton, with washer and dryer.
Historic Old Towne Southern Charm

Historic Old Towne Southern Charm

Portsmouth
With a stay at this vacation home in Portsmouth, you'll be within a 10-minute drive of Waterside District and Old Dominion University.
Historic Old Towne Southern Charm
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!
Spacious 7-bedroom house in brilliant Newport News with AC, WiFi

Spacious 7-bedroom house in brilliant Newport News with AC, WiFi

Newport News
The price is AU$1,869 per night from 7 Apr to 8 Apr
AU$1,869
includes taxes & fees
7 Apr - 8 Apr
With a stay at this vacation home in Newport News (North Newport News), you'll be within a 15-minute drive of Fort Eustis and Christopher Newport ...
Spacious 7-bedroom house in brilliant Newport News with AC, WiFi
Family friendly in Hampton with huge yard, dog park, and 2 blocks from the bay

Family friendly in Hampton with huge yard, dog park, and 2 blocks from the bay

Hampton
Located in Hampton (Downtown Hampton), this vacation home is within a 10-minute drive of Hampton Coliseum and Hampton University.
Family friendly in Hampton with huge yard, dog park, and 2 blocks from the bay
Pleasurable Escape Hampton

Pleasurable Escape Hampton

Hampton
With a stay at this vacation home in Hampton, you'll be a 3-minute drive from Langley Air Force Base and 6 minutes from Hampton Coliseum.
Pleasurable Escape Hampton
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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.

Windsor 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 Windsor vacation homes are the perfect way for you to wing it.

Holiday houses in Windsor 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 Windsor 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 Windsor adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Windsor 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 Windsor 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.

Windsor Holiday Homes essential information

Accommodation
276 Holiday Homes
Lowest Price
AU$156
Highest Price
AU$1,869
Popular accommodation
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home, NEW! Big Waterfront House w/ Amazing View and Swim Deck, Sojourn | Coastal Cottage | 3 BR, Charming 4-bedroom bungalow with AC and WiFi in Hampton, with washer and dryer., Historic Old Towne Southern Charm, The Cracker Jack House: A Military Salute & Arcade!, Spacious 7-bedroom house in brilliant Newport News with AC, WiFi, Family friendly in Hampton with huge yard, dog park, and 2 blocks from the bay, Pleasurable Escape Hampton

Top trending hotels in Windsor

Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

3.5 out of 5
1700 Coliseum Drive, Hampton, VA
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 13 Apr to 14 Apr
AU$156
includes taxes & fees
13 Apr - 14 Apr
With a stay at Embassy Suites by Hilton Hampton Convention Center, you'll be centrally located in Hampton, a 2-minute drive from Hampton Coliseum and 7 minutes ...
Embassy Suites by Hilton Hampton Convention Center
Sheraton Norfolk Waterside Hotel

Sheraton Norfolk Waterside Hotel

3.5 out of 5
777 Waterside Dr, Norfolk, VA
Fully refundableReserve now, pay when you stay
The price is AU$207 per night from 20 Apr to 21 Apr
AU$207
includes taxes & fees
20 Apr - 21 Apr
Located in Norfolk (Downtown Norfolk), Sheraton Norfolk Waterside Hotel is within a 5-minute drive of Norfolk Scope and Norfolk State University.
Sheraton Norfolk Waterside Hotel
Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St, Norfolk, VA
Fully refundableReserve now, pay when you stay
The price is AU$268 per night from 14 Apr to 15 Apr
AU$268
includes taxes & fees
14 Apr - 15 Apr
Norfolk Waterside Marriott is centrally located in Norfolk, a 2-minute walk from Waterside District and 15 minutes by foot from Harbor Park.
Norfolk Waterside Marriott
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Kingsmill Resort

Kingsmill Resort

4 out of 5
1010 Kingsmill Rd, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is AU$446 per night from 21 Apr to 22 Apr
AU$446
includes taxes & fees
21 Apr - 22 Apr
With a stay at Kingsmill Resort in Williamsburg (Kingsmill), you'll be within a 10-minute drive of Busch Gardens Williamsburg and College of William and ...
Kingsmill Resort
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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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^Subject to availability and chosen travel dates.