Painter Vacation Rentals

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Our top choices for Painter vacation rentals

Charming family friendly 3-bedroom house in Painter with AC and outdoor patio
10.0 out of 10, Exceptional, (61)
"A wonderful and relaxing stay. The house was well equipped and had everything we needed. The pool area was great and we enjoyed it daily, along with grilling and the fire pit. The perfect escape for this city family! "
United States
Vanda T.
Nassawadox Creek Waterfront Home with Private Pool
8.2 out of 10, Very Good, (28)
"From the outside the place looked kind of bare and not very outstanding. However, the inside was fine. Co.fortable bed and nice accommodations. "
United States
Cheryl T.
Perfect Cozy Vacation Rental on the Eastern Shore
9.4 out of 10, Exceptional, (14)
"We were very comfortable during our stay!"
United States
Anna H.
Secluded Seaside Village Retreat in Fishing Town
10.0 out of 10, Exceptional, (19)
"Excellent property in a beautiful location that is meticulously maintained."
United States
Jason S.
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
9.6 out of 10, Exceptional, (5)
"Very convenient location and Steve was very attentive to our needs - even the dog enjoyed the stay."
United States
William M.
$172 nightly
The price is $190
Dec 16 - Dec 17
Total with taxes and fees
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore
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."
United States
Bonnie R.
Waterfront, Gorgeous 4 BDR, 3 BA Beautiful views & sunsets
10.0 out of 10, Exceptional, (18)
"We enjoyed our stay so we could visit our granddaughter."
United States
Stephen S.
$323 nightly
The price is $356
Dec 12 - Dec 13
Total with taxes and fees
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3
10.0 out of 10, Exceptional, (124)
"Nice cottage in a great location"
United States
Jennifer T.
Charming Cottage - Ultimate Relaxation Destination
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. "
United States
LISA H.
Thelma’s Dawn Getaway! A true No Drama Zone
10.0 out of 10, Exceptional, (88)
"We had a great time at Colette’s and she was super communicative. Would recommend for a quiet, relaxing getaway!"
United States
Alyssa M.
Whimsical Cottage with Gorgeous Views of the Bay, overlooking Russell Marina.
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."
United States
Jesus
Oyster Cottage In Historic Fishing Village 2 Bedroom Cottage
10.0 out of 10, Exceptional, (2)
"Very clean beautiful home lots of room. Family oriented. Beautiful view,plentiful parking space quiet peaceful relaxing pla e to stay. Highly recommend for a wonderful vacation or getaway. "
United States
David E.
$479 nightly
The price is $528
Dec 15 - Dec 16
Total with taxes and fees
Waterfront Retreat- Relaxing Family Fun! King Bed, Private Dock great 4 Fishing!
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."
United States
John B.
Chesapeake Bay Retreat Private Dock + Beach
10.0 out of 10, Exceptional, (6)
"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!"
United States
Matt and Deborah A.
Visit waterfront Camp Belle Haven now!
9.2 out of 10, Wonderful, (158)
"Awesome! 4 friends.. 10 days.. so much fun! Peaceful, secluded, well stocked, great host! We'll be back "
United States
Cecelia H.
Remote/Secluded Estate with Plenty of Crabs, Dock and Cooking Station
10.0 out of 10, Exceptional, (20)
"This place is beautiful John was wonderful to work with we had a blast Thanks again John"
United States
Sherita C.
your own Private beach, adjacent nature preserve-Sunset Dunes Cape Charles, VA
10.0 out of 10, Exceptional, (11)
"Great stay easy access to Cape Charles and the beach"
United States
andrew c.
$317 nightly
The price is $355
Jan 4 - Jan 5, 2026
Total with taxes and fees
Pet Friendly Tiny Livin 3min from Cape Charles
10.0 out of 10, Exceptional, (26)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
$288 nightly
The price is $318
Dec 12 - Dec 13
Total with taxes and fees
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
10.0 out of 10, Exceptional, (28)
"We really enjoyed our stay. Plenty of space for a large family. Definitely would recommend other to stay here."
United States
Andre S.
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 8, and is pet friendly.
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

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 $190 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?

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 5 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 Parramore Beach.

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.