Painter Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Painter

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, (58)
"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

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

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 NZ$306
includes taxes & fees
6 Oct - 7 Oct
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-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

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.

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.

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

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

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

Pet Friendly Tiny Livin 3min from Cape Charles

10.0 out of 10, Exceptional, (11)
"Great location just across the highway from Cape Charles. Check in process was easy and house had everything you need for a short stay! "
The price is NZ$647
includes taxes & fees
8 Oct - 9 Oct
Pet Friendly Tiny Livin 3min from Cape Charles

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

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 NZ$499
includes taxes & fees
7 Oct - 8 Oct
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 NZ$289
includes taxes & fees
6 Oct - 7 Oct
Virginia Landing RV Campground

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

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

Thelma’s Dawn Getaway! A true No Drama Zone

10.0 out of 10, Exceptional, (158)
"Super friendly host and lovely cottage!! Steps from the bay with a private beach! Close to Cape Charles for food and shopping. "
Thelma’s Dawn Getaway! A true No Drama Zone

Counting Corks - Waterfront, Pet friendly, private dock!

10.0 out of 10, Exceptional, (10)
"Business travel for a job we were on this met our needs and was a good place to stay."
Counting Corks - Waterfront, Pet friendly, private dock!

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

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

Top Painter Hotel Reviews

Find out more about Painter

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 favorite 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 depends 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 NZ$289 per night. Entering your travel dates in the search wizard you might find 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?

Nassawadox Creek Waterfront Home with Private Pool: This holiday home rental outside of Painter is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Painter?

Expedia has 3 holiday 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 wider area, you’ll find The Blue Crow Antique Mall and North Street Market.

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.