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Check prices for these dates

Next weekend
Apr 4 - Apr 6
In two weeks
Apr 11 - Apr 13
In one month
Apr 25 - Apr 27
In two months
May 23 - May 25

Compare 11 Cottages in Painter with updated reviews, rates, and availability.

Virginia Retreat w/ Porch & Grill, Near Beaches!
Interior

Virginia Retreat w/ Porch & Grill, Near Beaches!

3.0 star property
Virginia Retreat w/ Porch & Grill, Near Beaches!
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

3.0 star property
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
Charming Cape Charles Vacation Rental Home!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Charming Cape Charles Vacation Rental Home!

3.0 star property
Charming Cape Charles Vacation Rental Home!
Charming Painter Home w/ Chesapeake Bay Views
Outdoor dining

Charming Painter Home w/ Chesapeake Bay Views

3.0 star property
8.0 out of 10, Very Good, (1)
Charming Painter Home w/ Chesapeake Bay Views
Unique Tangier Cottage w/ Chesapeake Bay Views!
Interior

Unique Tangier Cottage w/ Chesapeake Bay Views!

3.0 star property
Unique Tangier Cottage w/ Chesapeake Bay Views!
Home w/ Fire Pit < 1 Mi to Willis Wharf Boat Ramp!
Interior

Home w/ Fire Pit < 1 Mi to Willis Wharf Boat Ramp!

3.0 star property
Home w/ Fire Pit < 1 Mi to Willis Wharf Boat Ramp!
'cora's Cottage' Near Chesapeake Bay Access!
Interior

'cora's Cottage' Near Chesapeake Bay Access!

3.0 star property
'cora's Cottage' Near Chesapeake Bay Access!
Pet-friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
Beach

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

3.0 star property
Pet-friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
Spacious Cheriton Home: 8 Mi to Cape Charles!
TV, fireplace, books

Spacious Cheriton Home: 8 Mi to Cape Charles!

3.0 star property
Spacious Cheriton Home: 8 Mi to Cape Charles!
Bayfront Retreat w/ Game Room + Outdoor Pool!
Miscellaneous

Bayfront Retreat w/ Game Room + Outdoor Pool!

3.0 star property
Bayfront Retreat w/ Game Room + Outdoor Pool!
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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Frequently asked questions

Why book your cottage in Painter with Expedia?
Expedia has some superb cottages in Painter, so start planning for an unforgettable vacay on nature’s doorstep. If you’re on a budget, click on how much you want to spend and the star rating of your property. Or, try out our filters to search for cottages with a kitchen or a pool. We’ll help you find the perfect digs whatever your style of travel or plans.
How can I find cheap cottages in Painter?
The simplest way to get cheap cottages in Painter is with Expedia’s filter tool. Fine-tune your search results by star rating, budget and amenities to discover excellent rates in a few clicks.
What is there to do in Painter near my cottage?
If you’d like to discover the sights of Painter, be sure to stop by The Blue Crow Antique Mall. It’s a hit among locals and visitors alike.