Book Holiday Homes in Painter

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Featured Holiday Homes in Painter

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Machipongo
With a stay at this vacation home in Machipongo, you'll be within a 15-minute drive of Chatham Vineyards and Barrier Islands Center.
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool

Exmore
With a stay at this vacation home in Exmore, you'll be on the waterfront, and 10.3 mi (16.6 km) from Exmore Town Park and 10.4 mi (16.8 km) from Northampton ...
Nassawadox Creek Waterfront Home with Private Pool
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.

Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.

Cape Charles
When you stay at this vacation home in Cape Charles, you'll be within a 10-minute drive of University of Virginia Coastal Research Center and Cape Charles Museum ...
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.
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Bayfront Retreat w/ Game Room + Outdoor Pool!

Bayfront Retreat w/ Game Room + Outdoor Pool!

Exmore
When you stay at this vacation home in Exmore, you'll be on the waterfront and 14 minutes by car from Northampton Shopping Center.
Bayfront Retreat w/ Game Room + Outdoor Pool!
Whimsical Tiny House, Cape Charles Virginia

Whimsical Tiny House, Cape Charles Virginia

Cape Charles
The price is AU$429 per night from 5 Jan to 6 Jan
AU$429
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Cape Charles, this vacation home is by the sea, a 4-minute drive from Cape Charles Museum & Welcome Center and 5 minutes from Cape Charles Beach.
Whimsical Tiny House, Cape Charles Virginia
Huntington Farm - Great Family Retreat

Huntington Farm - Great Family Retreat

Cape Charles
Located in Cape Charles, this vacation home is on the waterfront, within a 10-minute drive of Cape Charles Museum & Welcome Center and Cape Charles Beach.
Huntington Farm - Great Family Retreat
Experience Tiny Living, in Cape Charles, Va

Experience Tiny Living, in Cape Charles, Va

Cape Charles
The price is AU$409 per night from 5 Jan to 6 Jan
AU$409
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Cape Charles, this vacation home is by the sea, a 4-minute drive from Cape Charles Museum & Welcome Center and 5 minutes from Cape Charles Beach.
Experience Tiny Living, in Cape Charles, Va
Thomas Inn Q 6 miles from Cape Charles - double room

Thomas Inn Q 6 miles from Cape Charles - double room

Cape Charles
This vacation home is 0.4 mi (0.7 km) from Northampton County Courthouse Historic District and 2.8 mi (4.4 km) from Indiantown Recreation Park.
Thomas Inn Q 6 miles from Cape Charles - double room
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

Hacksneck
With a stay at this vacation home in Hacksneck, you'll be on the beach, and 9 mi (14.5 km) from Eastern Shore Yacht and Country Club Golf Course and 9.3 mi (14.9 ...
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK
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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.

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

Holiday houses in Painter 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 Painter 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 Painter adventures, obvs.

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

Painter Holiday Homes essential information

Accommodation
59 Holiday Homes
Lowest Price
AU$170
Highest Price
AU$429
Popular accommodation
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks, Nassawadox Creek Waterfront Home with Private Pool, Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly., Bayfront Retreat w/ Game Room + Outdoor Pool!, Whimsical Tiny House, Cape Charles Virginia, Huntington Farm - Great Family Retreat, Experience Tiny Living, in Cape Charles, Va, Thomas Inn Q 6 miles from Cape Charles - double room, Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

Top trending hotels in Painter

Charming Painter Home w/ Chesapeake Bay Views

Charming Painter Home w/ Chesapeake Bay Views

Painter
With a stay at this vacation home in Painter, you'll be 8.8 mi (14.1 km) from Exmore Town Park and 9 mi (14.5 km) from Eastern Shore Yacht and Country Club Golf ...
Charming Painter Home w/ Chesapeake Bay Views
Charming Painter Home w/ Chesapeake Bay Views

Charming Painter Home w/ Chesapeake Bay Views

3 out of 5
Painter
With a stay at this cottage in Painter, you'll be 8.8 mi (14.1 km) from Exmore Town Park and 9 mi (14.5 km) from Eastern Shore Yacht and Country Club Golf ...
Charming Painter Home w/ Chesapeake Bay Views
Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay

Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay

Painter
With a stay at this vacation home in Painter, you'll be by the sea, and 8.4 mi (13.6 km) from Eastern Shore Yacht and Country Club Golf Course and 8.6 mi (13.9 ...
Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
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Hampton Inn & Suites Exmore - Eastern Shore

Hampton Inn & Suites Exmore - Eastern Shore

2.5 out of 5
4129 Lankford Hwy, Exmore, VA
Fully refundableReserve now, pay when you stay
The price is AU$170 per night from 3 Jan to 4 Jan
AU$170
includes taxes & fees
3 Jan - 4 Jan 2025
Located in Exmore, Hampton Inn & Suites Exmore - Eastern Shore is within a 5-minute drive of Northampton Shopping Center and Exmore Town Park.
Hampton Inn & Suites Exmore - Eastern Shore
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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.