Painter Vacation Rentals from CA $427: Short-Term Rentals for 2026

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Our top choices for Painter vacation rentals

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

1. The Lilliston - Short Stays on Market

Onancock

Jacob P.

CA $342 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Accomac

Deborah G.

CA $473 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Accomac

Rhiannon L.

CA $422 total

includes taxes & fees

Nov 6 - Nov 7

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

4. The Waverly Tree House

Machipongo

Jeanna C.

CA $398 total

includes taxes & fees

Nov 4 - Nov 5

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

Jayson J.

CA $600 total

includes taxes & fees

Dec 1 - Dec 2

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

6. 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.

CA $321 total

includes taxes & fees

Nov 8 - Nov 9

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.

7. The Oak - Short Stays on Market

Onancock

Betty A.

CA $305 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a brick wall, a bed with multiple pillows, a TV, and a chair.

8. The Social - Short Stays on Market

Onancock

Roscoe B.

CA $307 total

includes taxes & fees

Nov 16 - Nov 17

9. Family Getaway~ Game/Bunk Room~ King Bed~ Firepit!

Cape Charles

CA $750 total

includes taxes & fees

Nov 9 - Nov 10

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

10. Smith Beach cottage w/ private sunset

Cape Charles

Eileen D.

CA $590 total

includes taxes & fees

Nov 7 - Nov 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.

CA $479 total

includes taxes & fees

Nov 6 - Nov 7

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

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

Oyster

Jacob W.

CA $802 total

includes taxes & fees

Nov 4 - Nov 5

Bright open living space with modern kitchen island and cozy lounge

13. First Floor King Suite~ Family Friendly~ Games +Loft! Play by the Bay!

Tower Hill

CA $572 total

includes taxes & fees

Nov 17 - Nov 18

A two-story house with a porch, surrounded by trees and a grassy yard.

14. Angler’s Dream: Oyster VA Farmhouse w/ Water Views, Boat Ramp & Outdoor Shower

Oyster

CA $535 total

includes taxes & fees

Nov 4 - Nov 5

A wicker basket on a round wooden table in a room with a brown sofa and a lamp.

15. Marvelous Farm house style with 3-bedrooms in charming Cape Charles

Cape Charles

CA $489 total

includes taxes & fees

Nov 4 - Nov 5

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

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

Cape Charles

Kevin B.

CA $361 total

includes taxes & fees

Nov 4 - Nov 5

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

17. Tiny House Hideaway with King sized Bed

Cape Charles

Leslie

CA $405 total

includes taxes & fees

Nov 4 - Nov 5

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

18. Experience Tiny Living, in Cape Charles, Va

Cape Charles

Ella D.

CA $373 total

includes taxes & fees

Nov 22 - Nov 23

A beach scene with sand dunes and a boardwalk.

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

Cape Charles

William

CA $361 total

includes taxes & fees

Nov 4 - Nov 5

20. Tiny House close to the Beaches of Cape Charles

Cape Charles

Charles B.

CA $414 total

includes taxes & fees

Nov 4 - Nov 5

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Top Painter Hotel Reviews

Hampton Inn & Suites Exmore - Eastern Shore

10/10 Excellent

"Clean and comfy"

The Charlotte Hotel & Restaurant

10/10 Excellent

"A great hotel for a romantic getaway. The town of Onancock is the perfect size, small enough to be calm and peaceful, large enough to have a few restaurants, a coffee shop, and a few interesting antique shops. We were there over the halloween weekend, which was inspiring. A true family event, which includes all the shops welcoming the children. It's a great choice if you like pleasant surprises. We loved it."

Quality Inn & Suites Exmore - Eastern Shore

10/10 Excellent

"A huge shout out and thank you to the gentleman on the front desk the night I arrived. I had just been released from the emergency room for a broken arm, and this gentleman went out of his way to make sure that I had everything I needed. Under the circumstances, my stay could not have been better."

Nassawadox Creek Waterfront Home with Private Pool

10/10 Excellent

"So this place is so amazing we actually extended our stay until today. This house is exactly how it’s described… but, as far as we’re concerned. The osprey house is tranquil, not off the beaten path so far that you can’t go 30 minutes to the north or to the south and find so many things to go do. We enjoyed Cape Charles, we even went back over the bridge and if you have easy pass you should bring it with you because it’s 16 one way but if you do it in less than 24 hours it’s only six dollars coming back. It is definitely worth the trip if you’d like to go into Maine city areas, or if you’re like my husband and I who love to go antiquing or the thrift stores, the art Studios or museums. But we also love to fish and crab so the fishing is spectacular over there as well as Cape Charles , Kiptopeke state park, as well as Chincoteague island. But, our best crabbing was here at Osprey house we caught nothing but number ones and number two which are everything over 7 inches. We made sure we threw back all of the females because we definitely want to have crabs all year round and for the future. Now most people would think this time of the year is not a good time to come out to fish or crab if that’s what you’d like to do but it is I grew up here on the Eastern shore and this is the best time to come in and get crabs and clams and oysters and everything else that has to do with seafood. The sunrises here are gorgeous, the property is an amazing park like setting. Booking next year."

Budget Inn

10/10 Excellent

"I’ve stay here before and will again. Being a snowbird Flordia to Rhode Island. As the name says it’s a Budget Hotel. Much nicer than other hotels. Clean, affordable AND allows pets. One suggestion would be grip strips on the shower floor. It’s fiberglass and with soap n shampoo it gets slippery there. I like seeing properties being taken care of. So as I told the front desk I’ll be back on my way home to RI in May."

Bayfront Retreat w/ Game Room + Outdoor Pool!

10/10 Excellent

"This was our third visit to the bay front retreat, and we had another wonderful time! Such a lovely house and property, well off the beaten path, surrounded by nature! The house was clean and well stocked with everything we needed for a great time! The host, Mary, was super attentive and helpful when needed. We will definitely be back next year!"

Find out more about Painter

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Painter. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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. The Lilliston - Short Stays on Market

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

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

4. The Waverly Tree House

5. Nassawadox Creek Waterfront Home with Private Pool

6. The Harbour - Short Stays on Market

7. The Oak - Short Stays on Market

8. The Social - Short Stays on Market

9. Family Getaway~ Game/Bunk Room~ King Bed~ Firepit!

10. Smith Beach cottage w/ private sunset

11. Unique Tangier Cottage w/ Chesapeake Bay Views!

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

13. First Floor King Suite~ Family Friendly~ Games +Loft! Play by the Bay!

14. Angler’s Dream: Oyster VA Farmhouse w/ Water Views, Boat Ramp & Outdoor Shower

15. Marvelous Farm house style with 3-bedrooms in charming Cape Charles

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

17. Tiny House Hideaway with King sized Bed

18. Experience Tiny Living, in Cape Charles, Va

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

20. Tiny House close to the Beaches of Cape Charles

Find vacation rentals that suit your style

Top Painter Hotel Reviews

Hampton Inn & Suites Exmore - Eastern Shore

The Charlotte Hotel & Restaurant

Quality Inn & Suites

Quality Inn & Suites Exmore - Eastern Shore

Nassawadox Creek Waterfront Home with Private Pool

Cape Charles Tiny Livin

Budget Inn

Bayfront Retreat w/ Game Room + Outdoor Pool!

Waterfront Oasis with Crabs, Oysters and Mother Nature

Find out more about Painter

Frequently asked questions

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