Painter Vacation Rentals

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Vacation Rentals in Painter

Our top choices for Painter vacation rentals

Pet-friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay

3.0 star property
Pet-friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (57)
"Beautiful property and house. Everything was very clean. Great neighbors who helped us out in a pinch. And Nancy, our host, so kind and gracious. I hope to come back many more times."
Nassawadox Creek Waterfront Home with Private Pool

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (124)
"Very nice cute cottage, well stocked. only downfall is that windows don't open in some of the rooms due to age and excess paint."
Charming Cottage - Ultimate Relaxation Destination

Perfect Cozy Vacation Rental on the Eastern Shore

8.2 out of 10, Very Good, (27)
"Dated and not modern, clean but not a getaway or vacation rental, stove and oven dirty, only a few dishwater items available. "
Perfect Cozy Vacation Rental on the Eastern Shore

Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

9.6 out of 10, Exceptional, (22)
"We enjoyed our stay - everything was provided and comfortable. We definitely recommend the location - could go kayaking, biking, and enjoy the back porch every day."
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

Remote/Secluded Estate with Plenty of Crabs, Dock and Cooking Station

9.2 out of 10, Wonderful, (158)
"We had an absolute blast over Memorial Day weekend! The house was the perfect getaway — peaceful, relaxing, and full of little adventures. The pier was a highlight for us. We caught 3 stingrays, 2 eels, fish, crab, and even oysters — such a fun variety that kept us on our toes!It was also such a treat to bring our dogs along and include our fur family in the fun. We enjoyed dinner every night in the screened-in patio and sipped coffee each morning on the upstairs deck — just the kind of relaxing...
Remote/Secluded Estate with Plenty of Crabs, Dock and Cooking Station

A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

10.0 out of 10, Exceptional, (3)
"Very convenient location and Steve was very attentive to our needs - even the dog enjoyed the stay."
The price is ¥8,465
¥29,037 total
includes taxes & fees
Sep 29 - Sep 30
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

Newly renovated, 4BD 2 BA, 1 full acre, sleeps 8, and is pet friendly.

10.0 out of 10, Exceptional, (26)
"The house was everything and more. Great place to unwind. The host was very helpful and easy to get in touch with. close to everything. Thank you for a memorable trip, Bill"
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 8, and is pet friendly.

Oyster Cottage In Historic Fishing Village 2 Bedroom Cottage

3.0 star property
10.0 out of 10, Exceptional, (2)
"The cottage was perfect. Very clean, extremely well stocked kitchen, linens were nice quality and comfortable, beautiful location, outdoor shower, lots of outdoor space and screened in porch. Will be staying there again for sure."
Oyster Cottage In Historic Fishing Village 2 Bedroom Cottage

Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

10.0 out of 10, Exceptional, (57)
"Enjoyed the well stocked home filled with everything from kayaks, sun umbrellas and chairs to big spray. Had a wonderful time!"
Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

1903 By the Sea - Minutes from Cape Charles

2.0 star property
9.0 out of 10, Wonderful, (4)
"Was looking for a clean, quiet place for our family vacation and this place was wonderful. Woody was very helpful and answered my questions quickly and informatively. The big yard was wonderful for our dog to run around in and did I mention that this place was CLEAN? Nice screened in back porch, fire pit and grill for our use. I will definitely book here again in the future "
1903 By the Sea - Minutes from Cape Charles

Waterfront, Gorgeous 4 BDR, 3 BA Beautiful views & sunsets

10.0 out of 10, Exceptional, (4)
"We enjoyed our stay. The house, views, location, kitchen, water, and yard were great! The access to the bay was a little tricky and had a bunch of strangers using it too."
Waterfront, Gorgeous 4 BDR, 3 BA Beautiful views & sunsets

Chesapeake Bay Retreat Private Dock + Beach

10.0 out of 10, Exceptional, (3)
"Wonderful house and phenomenal lot. Very well appointed and extremely well stocked. The lot is absolutely amazing…private, serene and gorgeous views on the water. We’ll definitely return."
Chesapeake Bay Retreat Private Dock + Beach

your own Private beach, adjacent nature preserve-Sunset Dunes Cape Charles, VA

10.0 out of 10, Exceptional, (20)
"This place is beautiful John was wonderful to work with we had a blast Thanks again John"
your own Private beach, adjacent nature preserve-Sunset Dunes Cape Charles, VA

Whimsical Cottage with Gorgeous Views of the Bay, overlooking Russell Marina.

10.0 out of 10, Exceptional, (85)
"We enjoyed our stay at the Farmhouse! The owners were great to communicate with, they give wonderful advice of things to do and places to eat on the Eastern Shore! We would definitely recommend staying here if you are visiting the area! "
Whimsical Cottage with Gorgeous Views of the Bay, overlooking Russell Marina.

Pet Friendly Tiny Livin 3min from Cape Charles

9.8 out of 10, Exceptional, (9)
"Clean and comfortable cabin, with a nice communal outdoor space. Host lit a fire in the firepit for the evening. Close to Cape Charles and Kiptopeke park."
The price is ¥44,135
¥54,853 total
includes taxes & fees
Oct 8 - Oct 9
Pet Friendly Tiny Livin 3min from Cape Charles

Thelma’s Dawn Getaway! A true No Drama Zone

10.0 out of 10, Exceptional, (158)
"Location is key here along w/on-site host's concern w/keeping all happy and entertained. Had a great few days!"
Thelma’s Dawn Getaway! A true No Drama Zone

Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

10.0 out of 10, Exceptional, (1)
"This was a great stay, we loved everything about it. Highly recommended. We will definitely return."
The price is ¥33,950
¥42,132 total
includes taxes & fees
Oct 2 - Oct 3
Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

Virginia Landing RV Campground

2.0 star property
8.0 out of 10, Very Good, (36)
The price is ¥22,584
¥24,910 total
includes taxes & fees
Sep 29 - Sep 30
Virginia Landing RV Campground

Visit waterfront Camp Belle Haven now!

10.0 out of 10, Exceptional, (3)
"Stayed here with my parents, husband, and adult children - we had a family wedding nearby. Fantastic location and great, comfortable house with lots of gathering places - we thoroughly enjoyed the 3 season room, and my adult children took advantage of the dock and kayak! The property manager allowed us to bring our dog with us (for a pet fee) which was greatly appreciated!"
Visit waterfront Camp Belle Haven now!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Painter Hotel Reviews

Find out more about Painter

Find out more about Painter

Search for holiday rentals in Painter on Expedia! You can easily find your home rentals, villas, holiday apartments in Painter using one of the methods below:

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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?

Nassawadox Creek Waterfront Home with Private Pool: Visitors like this Painter vacation home rental. It is located on the waterfront and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Painter?

Expedia has 3 vacation rentals for your stay in Painter.

What can I see and do in Painter?

Explore the area and family-friendly sights such as SouthEast Expeditions, or get out into nature at a spot like Parramore Beach. In the larger area, you’ll find The Blue Crow Antique Mall and North Street Market.

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.