Painter Holiday Rentals : Search Short-Term Rentals

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

Waterfront Oasis with Crabs, Oysters and Mother Nature : This holiday home rental outside of Painter is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a private garden and a selection of games.

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Our top choices for Painter holiday rentals

1. The Glick - Short Stays on Market

Onancock

"The Glick was a find! This spacious, nicely decorated one bedroom apartment is in the center of town and has all you need for two people. The king bed and sheets were comfortable, the place was spotless, there were plenty of towels and the water pressure was great in the shower. The kitchen is large with a Keurig coffee maker, and stocked with plates and cooking utensils. And there is a washer/dryer (one unit) in that space, which we used one time and worked great.We were very comfortable, and...

Sue E.

includes taxes & fees

22 Sept - 23 Sept

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

Accomac

Karen K.

includes taxes & fees

21 Sept - 22 Sept

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

Accomac

Deborah G.

includes taxes & fees

29 Sept - 30 Sept

4. Stunning Waterfront Home with Private Dock - Wright on the Water!

Belle Haven

Linda L.

includes taxes & fees

27 Sept - 28 Sept

5. 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.

includes taxes & fees

16 Sept - 17 Sept

6. The Lilliston - Short Stays on Market

Onancock

includes taxes & fees

15 Sept - 16 Sept

1 bedroom, iron/ironing board, WiFi, bed sheets

7. The Social - Short Stays on Market

Onancock

Roscoe B.

includes taxes & fees

15 Sept - 16 Sept

8. The Waverly Tree House

Machipongo

Jeanna C.

includes taxes & fees

15 Sept - 16 Sept

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Top Painter Hotel Reviews

Hampton Inn & Suites Exmore - Eastern Shore

10/10 Excellent

"Clean. Comfortable. Professional courteous staff. Good breakfast. Easy parking"

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! :)"

The Charlotte Hotel & Restaurant

8/10 Good

"The hotel is in a cute town that's walkable, with plenty of restaurants and shops. The property is managed like an Airbnb, so no staff were on-site when we checked in or when we left. The check-in process was quick and easy, with the keys left at the front desk. The bathrooms included all the nice amenities like hair care, etc. The hotel is quaint, and they have a lot to offer -- I had only one complaint. The fire alarm battery in reception was dying so it chirped every few minutes. I called the after-hours contact line at 8:30 pm and explained that it could be heard throughout the hotel (which is an old house). No one came by, and it continued to chirp all night. The good news is, I'm sure the battery has been replaced so you won't have to worry about it!"

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"

Find out more about Painter

Everything you need to know about Painter holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Painter holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Painter holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Painter holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Painter holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Painter rentals

At Expedia, we put the best Painter holiday 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 holiday.

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 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?

Waterfront Oasis with Crabs, Oysters and Mother Nature: This holiday home rental outside of Painter is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a private garden and a selection of games.

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 Parramore Beach.

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. The Glick - 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. Stunning Waterfront Home with Private Dock - Wright on the Water!

5. The Harbour - Short Stays on Market

6. The Lilliston - Short Stays on Market

7. The Social - Short Stays on Market

8. The Waverly Tree House

9. Nassawadox Creek Waterfront Home with Private Pool

10. Unique Tangier Cottage w/ Chesapeake Bay Views!

11. Smith Beach cottage w/ private sunset

12. As close as you can get to the ocean south of Chincoteague

13. Coastal 4BR Retreat, Spacious Deck, Minutes to Cape Charles Beach

14. Tiny House close to the Beaches of Cape Charles

15. Tiny House 3 min from Down Town Cape Charles

16. Unique Tangier Cottage w/ Chesapeake Bay Views!

17. Pet Friendly Tiny Livin 3min from Cape Charles

18. Tiny House Hideaway with King sized Bed

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

Find holiday rentals that suit your style

Top Painter Hotel Reviews

Hampton Inn & Suites Exmore - Eastern Shore

Quality Inn & Suites Exmore - Eastern Shore

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

The Charlotte Hotel & Restaurant

Awesome private off grid cabin with creek view.

1903 By the Sea - Minutes from Cape Charles

Smith Beach cottage w/ private sunset

Quality Inn & Suites

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

Find out more about Painter

Frequently asked questions

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