Painter Vacation Rentals from ￥39,589: Search Short-Term Rentals

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Our top choices for Painter vacation 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

￥27,684 total

includes taxes & fees

Oct 7 - Oct 8

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

2. The Lilliston - Short Stays on Market

Onancock

Jacob P.

￥38,487 total

includes taxes & fees

Oct 14 - Oct 15

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.

￥56,255 total

includes taxes & fees

Oct 14 - Oct 15

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

4. Nassawadox Creek Waterfront Home with Private Pool

Exmore

Rita T.

￥73,027 total

includes taxes & fees

Nov 1 - Nov 2

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

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

Accomac

Karen K.

￥49,988 total

includes taxes & fees

Oct 11 - Oct 12

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

6. The Waverly Tree House

Machipongo

Jeanna C.

￥59,909 total

includes taxes & fees

Oct 7 - Oct 8

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

7. The Glick - Short Stays on Market

Onancock

"Our weekend stay at The Glick was perfect!! The apartment was very clean, comfortable and nicely decorated, just like the pictures show. We really appreciated the Keurig coffee machine and comfy bed. All instructions for check in and check out were very clear and simple. We were within walking distance to several restaurants and shops. The town of Onancock is so peaceful and charming. The sunsets at the Wharf are beautiful. This is a wonderful location to stay while visiting on the Eastern Shore"

Tara M.

￥38,332 total

includes taxes & fees

Oct 11 - Oct 12

A living room with a brick wall, two windows, a television, a wicker chair, a sofa, and a lamp.

8. The Harbour - Short Stays on Market

Onancock

"The Harbour on Market in Onancock, VA was a gorgeous condo and we will absolutely love to vacation here again in the future. Everything was top notch and the amenities surpassed our expectations. We had an unfortunate incident beyond anyone’s control and needed to vacate sooner than expected; however, the owners were so amazing and accommodated our needs. We highly recommend this place! 5 FULL STARS!"

Jennifer M.

￥39,589 total

includes taxes & fees

Oct 26 - Oct 27

A bedroom with a brick wall, a bed with a green headboard, a wooden dresser, a chair, a flat-screen TV, and a large window.

9. The Oak - Short Stays on Market

Onancock

Betty A.

￥36,119 total

includes taxes & fees

Oct 22 - Oct 23

A kitchen with granite countertops, a black refrigerator, a microwave, a toaster, and wooden cabinets.

10. Oyster Harbor Cottage – Where the Only Limit Is Your Imagination

Oyster

Jacob W.

￥92,150 total

includes taxes & fees

Oct 7 - Oct 8

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

11. Unique Tangier Cottage w/ Chesapeake Bay Views!

Tangier

Tim B.

￥64,073 total

includes taxes & fees

Oct 7 - Oct 8

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

12. Smith Beach cottage w/ private sunset

Cape Charles

Ryan M.

￥70,006 total

includes taxes & fees

Oct 12 - Oct 13

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

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

Cape Charles

Kevin B.

￥42,504 total

includes taxes & fees

Oct 7 - Oct 8

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

14. Tiny House Hideaway with King sized Bed

Cape Charles

Leslie

￥48,872 total

includes taxes & fees

Nov 2 - Nov 3

15. Tiny House close to the Beaches of Cape Charles

Cape Charles

Charles B.

￥48,993 total

includes taxes & fees

Oct 7 - Oct 8

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

16. Pet Friendly Tiny Livin 3min from Cape Charles

Cape Charles

andrew c.

￥55,307 total

includes taxes & fees

Oct 7 - Oct 8

A beach scene with sand dunes and a boardwalk.

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

Cape Charles

William

￥42,504 total

includes taxes & fees

Oct 7 - Oct 8

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

18. Tiny House 3 min from Down Town Cape Charles

Cape Charles

Robert

￥51,041 total

includes taxes & fees

Oct 7 - Oct 8

19. Whimsical Tiny House, Cape Charles Virginia

Cape Charles

Cathy W.

￥55,329 total

includes taxes & fees

Oct 7 - Oct 8

20. Unique Tangier Cottage w/ Chesapeake Bay Views!

Tangier

￥62,336 total

includes taxes & fees

Oct 7 - Oct 8

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Top Painter Hotel Reviews

Hampton Inn & Suites Exmore - Eastern Shore

8/10 Good

"We had stayed at a competitor facility in Exmore previously and were expecting more of the same. The overall quality of the Hampton was a surprising step above! The only drawback was the absence of a refrigerator in our room where we had hoped we might store certain medicines."

Awesome private off grid cabin with creek view.

10/10 Excellent

"This is the 3rd time my husband and I have come out to this little gem of a hidden spot. We absolutely love bringing our dogs out here to disconnect. Terri always answers and is very easy to get ahold of if need be. The best spot to disconnect!"

Unique Tangier Cottage w/ Chesapeake Bay Views!

10/10 Excellent

"Had a great time The place was beautifully decorated and I especially enjoyed the 2nd floor veranda overlooking the bay facing West at sunset. We found the locals to be very friendly and informative, adding to the enjoyment of our stay. All in all, I would say it was a relaxing time, and I would definitely go back again"

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! :)"

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 vacation rentals in Painter?

Yes, you can find vacation rentals close to top local attractions in Painter, or you can select a more secluded option if you'd like a relaxing place to stay. Painter is known for its museums.

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

Charming family friendly 3-bedroom house in Painter with AC and outdoor patio: Visitors like this Painter vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Painter?

Expedia has 4 vacation 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 larger area, you’ll find The Blue Crow Antique Mall and Northampton Shopping Center.

What are vacation rentals like in Painter?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Painter. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for small groups.

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Check prices for these dates

Our top choices for Painter vacation rentals

1. Virginia Landing RV Campground

2. The Lilliston - Short Stays on Market

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

4. Nassawadox Creek Waterfront Home with Private Pool

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

6. The Waverly Tree House

7. The Glick - Short Stays on Market

8. The Harbour - Short Stays on Market

9. The Oak - Short Stays on Market

10. Oyster Harbor Cottage – Where the Only Limit Is Your Imagination

11. Unique Tangier Cottage w/ Chesapeake Bay Views!

12. Smith Beach cottage w/ private sunset

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

14. Tiny House Hideaway with King sized Bed

15. Tiny House close to the Beaches of Cape Charles

16. Pet Friendly Tiny Livin 3min from Cape Charles

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

18. Tiny House 3 min from Down Town Cape Charles

19. Whimsical Tiny House, Cape Charles Virginia

20. Unique Tangier Cottage w/ Chesapeake Bay Views!

Find vacation rentals that suit your style

Top Painter Hotel Reviews

Hampton Inn & Suites Exmore - Eastern Shore

Awesome private off grid cabin with creek view.

The Charlotte Hotel & Restaurant

Quality Inn & Suites

Unique Tangier Cottage w/ Chesapeake Bay Views!

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

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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