Painter Vacation Rentals from $244: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

"This is a gorgeous property! From the entrance/foyer to the closets it's top notch. You can't match the convenience in the heart of downtown Onancock and the walkability to just about anything. This is like staying in a friend's luxe apartment - sure, you're on vacation, but staying inside isn't such a bad thing, either! After an active day, you can wind down in a beautiful space and people watch through the windows. As much as I love to treat myself to dining out when I'm in Onancock, I...

Anonymous traveler

$221 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

Rhiannon L.

$261 nightly

Nov 13 - Nov 14

Total with taxes and fees

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.

$292 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

4. 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.

$209 nightly

Nov 11 - Nov 12

Total with taxes and fees

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.

5. The Oak - Short Stays on Market

Onancock

Betty A.

$198 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

6. Nassawadox Creek Waterfront Home with Private Pool

Exmore

Jayson J.

$375 nightly

Dec 1 - Dec 2

Total with taxes and fees

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

7. The Waverly Tree House

Machipongo

Jeanna C.

$246 nightly

Nov 11 - Nov 12

Total with taxes and fees

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.

$190 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

9. Smith Beach cottage w/ private sunset

Cape Charles

Eileen D.

$352 nightly

Nov 11 - Nov 12

Total with taxes and fees

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.

$513 nightly

Nov 11 - Nov 12

Total with taxes and fees

A patio with a metal fire pit, two chairs with cushions, and a wooden table.

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

Cape Charles

$460 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

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

Oyster

$335 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

$343 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

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

Cape Charles

View all properties

Find vacation rentals that suit your style

Cottages

Private vacation homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Painter Hotel Reviews

Hampton Inn & Suites Exmore - Eastern Shore

10/10 Excellent

"Staff very friendly, easy check in,room was clean. Did not eat breakfast as we left very early. Would stay again"

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."

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!"

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!"

Find out more about Painter

Everything you need to know about Painter vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Painter vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Painter vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Painter vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Painter. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Painter in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $244 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Painter rentals

At Expedia, we put the best Painter vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Painter rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Painter vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Painter. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Painter vacation rentals

1. The Lilliston - Short Stays on Market

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 Harbour - Short Stays on Market

5. The Oak - Short Stays on Market

6. Nassawadox Creek Waterfront Home with Private Pool

7. The Waverly Tree House

8. The Social - Short Stays on Market

9. Smith Beach cottage w/ private sunset

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

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

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

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

14. Marvelous Farm house style with 3-bedrooms in charming 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

Bayfront Retreat w/ Game Room + Outdoor Pool!

Waterfront Oasis with Crabs, Oysters and Mother Nature

Awesome private off grid cabin with creek view.

Find out more about Painter

Frequently asked questions

Go further with the Expedia app