Painter Holiday Rentals: Short-Term Accommodations for Rent

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In two weeks

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Our top choices for Painter holiday rentals

A room with a wooden floor, a white wicker sofa, a wicker armchair, a wooden dining table with four chairs, and a door with a window.

1. Virginia Landing RV Campground

Quinby

"If you’re looking for a resort atmosphere, this isn’t it—and that’s exactly the point. If you want a beautiful, peaceful place to reset, unplug, and escape for a while, you’ve just hit the jackpot. Every second of our stay was perfect. I read all of the reviews beforehand, so I knew what to expect and came prepared. It was everything I hoped it would be and more. We will absolutely be back—without a single doubt."

Nicole

HK$1,376 total

includes taxes & fees

5 Oct - 6 Oct

A staircase with a dark door at the bottom and a light fixture above it.

2. Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Accomac

Karen K.

HK$2,494 total

includes taxes & fees

11 Oct - 12 Oct

A two-story house with a front porch, a number '23314' on the door, and a small bench.

3. Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

Accomac

Deborah G.

HK$2,797 total

includes taxes & fees

12 Oct - 13 Oct

A hallway with striped sofas, a wooden floor, and wall-mounted lights.

4. The Glick - Short Stays on Market

Onancock

HK$1,897 total

includes taxes & fees

4 Oct - 5 Oct

A house surrounded by dense greenery and a small dock extending into a body of water.

5. Nassawadox Creek Waterfront Home with Private Pool

Exmore

Rita T.

HK$3,664 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a stainless steel refrigerator, a dark wall with framed artwork, and a brick wall with a hanging light fixture.

6. The Lilliston - Short Stays on Market

Onancock

Sena B.

HK$1,823 total

includes taxes & fees

5 Oct - 6 Oct

A wooden deck with a chair, a welcome mat, and a view of a forest.

7. The Waverly Tree House

Machipongo

Jeanna C.

HK$2,961 total

includes taxes & fees

5 Oct - 6 Oct

A wooden deck with a white fence and a lounge chair, overlooking a calm body of water during sunset.

8. Smith Beach cottage w/ private sunset

Cape Charles

Ryan M.

HK$3,480 total

includes taxes & fees

6 Oct - 7 Oct

A modern kitchen with wooden ceiling, white cabinets, stainless steel appliances, and a central island with seating.

9. Unique Tangier Cottage w/ Chesapeake Bay Views!

Tangier

Tim B.

HK$3,185 total

includes taxes & fees

5 Oct - 6 Oct

A beach with a long stretch of sand, a few scattered rocks, and a distant shoreline with buildings.

10. Restored 1930’s Tiny Home 3 min to Cape Charles

Cape Charles

Kevin B.

HK$2,145 total

includes taxes & fees

6 Oct - 7 Oct

A beach at sunset with a calm sea, a sandy shore, and a pier extending into the water.

11. Experience Tiny Living, in Cape Charles, Va

Cape Charles

Ella D.

HK$2,049 total

includes taxes & fees

5 Oct - 6 Oct

A spacious bedroom with a large bed, wooden beams on the ceiling, and a view of the outdoors through the windows.

12. Tiny House Hideaway with King sized Bed

Cape Charles

Leslie

HK$2,535 total

includes taxes & fees

1 Nov - 2 Nov

13. Tiny House close to the Beaches of Cape Charles

Cape Charles

Charles B.

HK$2,410 total

includes taxes & fees

5 Oct - 6 Oct

A beach scene with sand dunes and a boardwalk.

14. Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

Cape Charles

William

HK$2,194 total

includes taxes & fees

13 Oct - 14 Oct

15. Pet Friendly Tiny Livin 3min from Cape Charles

Cape Charles

andrew c.

HK$2,723 total

includes taxes & fees

5 Oct - 6 Oct

A beach with a sandy shore, a few scattered rocks, and a distant shoreline with vegetation and buildings.

16. Whimsical Tiny House, Cape Charles Virginia

Cape Charles

Cathy W.

HK$2,723 total

includes taxes & fees

5 Oct - 6 Oct

17. Unique Tangier Cottage w/ Chesapeake Bay Views!

Tangier

HK$3,099 total

includes taxes & fees

5 Oct - 6 Oct

18. Tiny House 3 min from Down Town Cape Charles

Cape Charles

Robert

HK$2,520 total

includes taxes & fees

5 Oct - 6 Oct

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Top Painter Hotel Reviews

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

10/10 Excellent

"Everything was excellent staff clean breakfast and polite"

Pet-Friendly Waterfront Retreat w/ Private Dock on Virginia’s Eastern Shore

10/10 Excellent

"My family had an awesome time over Labor Day weekend staying at Ripple! (While we waited for the house to be ready, we took a short trip to Kiptopeke and saw the concrete ships. So cool!)Ripple was the perfect place to celebrate our 25th wedding anniversary with our children, 21 and 24. It was peaceful, relaxing, clean and comfortable, and had a beautiful view. We made sure to take our fishing gear, and spent a lot of our time out on the pier catching croakers, speckled sea trout (?), and our very first cobias!We are already talking about our next stay at Ripple. That time can't come soon enough! :)"

Awesome private off grid cabin with creek view.

10/10 Excellent

"We almost don’t want to leave this review because we’d really prefer everyone else NOT discover this place so it’s available the next time we want to go. But… here we are, doing the right thing.Three friends, dogs, water views, acres and acres of soybean fields, and basically no people. It was glorious."Peaceful, comfortable, beautiful nature getaway. I’ll be returning. You should all stay away" and "Peaceful and convenient getaway. Very well equipped" - LLL & ERThe view is absolutely beautiful, and the property is wonderfully secluded. We took long, peaceful walks along the soybean fields, sat by the water, and thoroughly enjoyed feeling like we had disappeared from civilization for a while. The dogs were equally impressed and would probably give it six stars if VRBO allowed them to have accounts.Inside, the house is adorable, comfortable, and thoughtfully done. The kitchen was surprisingly well stocked, and the owners even left homemade s’mores kits for us, which was such a cute touch and immediately made us feel like someone had planned our grown-up camping trip better than we had.One thing worth knowing: this probably isn’t the place for everyone. It’s truly off the grid, powered by solar with a backup generator, and it is SECLUDED. If your idea of vacation is water, fields, dogs, quiet, stars, s’mores, and not seeing another human unless you invited them… book it.Actually, don’t. We want to go back.Shannon, Laura Lee and Elisabeth"

Regal Inn

10/10 Excellent

"We took 2 rooms during a road trip, arriving close to midnight with our extended family of 6. We only stayed one night, mainly to rest, and overall it served that purpose very well. On the positive side, the place was clean, The beds were comfortable, and it was a very good value for money. We were able to get a good night’s rest after a long drive. The only downside was the noisy air conditioning, which made it a bit less comfortable during the night. Overall, it was a good short stay and met our basic needs for a stopover (at that budget price!)"

Find out more about Painter

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Frequently asked questions

Are there holiday rentals in Painter?

Yes, there are holiday rentals close to the most popular sights in Painter, or you can select a more secluded option if you're looking for a relaxing stay. Painter is known for its museums.

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

Charming family friendly 3-bedroom house in Painter with AC and outdoor patio: This highly rated holiday home rental in Painter has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Painter?

Expedia has 4 holiday rentals for your stay in Painter.

What can I see and do in Painter?

Explore the area and family-friendly sights such as North Street Market, or get out into nature at a spot like Chesapeake Bay. In the wider area, you’ll find The Blue Crow Antique Mall and Northampton Shopping Center.

What are holiday rentals like in Painter?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Painter. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.

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Check prices for these dates

Our top choices for Painter holiday rentals

1. Virginia Landing RV Campground

2. Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

3. Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

4. The Glick - Short Stays on Market

5. Nassawadox Creek Waterfront Home with Private Pool

6. The Lilliston - Short Stays on Market

7. The Waverly Tree House

8. Smith Beach cottage w/ private sunset

9. Unique Tangier Cottage w/ Chesapeake Bay Views!

10. Restored 1930’s Tiny Home 3 min to Cape Charles

11. Experience Tiny Living, in Cape Charles, Va

12. Tiny House Hideaway with King sized Bed

13. Tiny House close to the Beaches of Cape Charles

14. Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

15. Pet Friendly Tiny Livin 3min from Cape Charles

16. Whimsical Tiny House, Cape Charles Virginia

17. Unique Tangier Cottage w/ Chesapeake Bay Views!

18. Tiny House 3 min from Down Town Cape Charles

Find holiday rentals that suit your style

Top Painter Hotel Reviews

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

The Charlotte Hotel & Restaurant

Quality Inn & Suites

Nassawadox Creek Waterfront Home with Private Pool

Pet-Friendly Waterfront Retreat w/ Private Dock on Virginia’s Eastern Shore

Awesome private off grid cabin with creek view.

Counting Corks | Waterfront Pet Friendly Cottage w/ Dock for Crabbing, Firepit & Near Cape Charles

Regal Inn

Budget Inn

Find out more about Painter

Frequently asked questions

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