Painter Vacation Rentals

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Vacation Rentals in Painter

Charming Painter Home w/ Chesapeake Bay Views
Beach
Charming Painter Home w/ Chesapeake Bay Views
8.2 out of 10, Very Good, 42 reviews
"Stayed here to go fishing worked out great"
Charming Painter Home w/ Chesapeake Bay Views
Charming Painter Home w/ Chesapeake Bay Views
Interior
Charming Painter Home w/ Chesapeake Bay Views
3.0 star property
Charming Painter Home w/ Chesapeake Bay Views
Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
Beach
Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
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Cute and Cozy Vacation Stay on the Eastern Shore!
Cute and Cozy Vacation Stay on the Eastern Shore!
8.8 out of 10, Excellent, 52 reviews
"Tv only had one channel and floors were very dirty but I bought mop and cleaned them up not a problem everyone there I spoke to was very nice"
Cute and Cozy Vacation Stay on the Eastern Shore!
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK
9.4 out of 10, Exceptional, 142 reviews
"The stay was great if you don’t mind cameras watching you. Propane tank was empty, couldn’t sit on balcony because straw would go up my ass from the crappy chairs. Stove top was dirty with mysterious fluid. It was what it was. Plenty to do in area. Plenty of undersize crab available- we threw them back."
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK
As close as you can get to the ocean south of Chincoteague
Property grounds
As close as you can get to the ocean south of Chincoteague
10.0 out of 10, Exceptional, 124 reviews
"We really enjoyed our stay at this little slice of paradise! The views from the screened in porch or the back decks we’re just beautiful. It truly is a birders paradise with bald eagles, purple Martins, Barnes swallows, mockingbird, willets And an abundance of shorebirds. The house was very well stocked including hand soap, dish soap, paper towels, toilet paper, coffee filter and much more. I did bring my own kayaks but really didn’t need to because there were nice ones there for guest use. The...
The price is $300
$502 total
includes taxes & fees
Jun 16 - Jun 17
As close as you can get to the ocean south of Chincoteague
Awesome private off grid cabin with creek view.
Property grounds
Awesome private off grid cabin with creek view.
9.4 out of 10, Exceptional, 10 reviews
"It is pretty basic, but equiped with all necessities and nicely put together. A cozy cabin with a lot of history. No street noise, no neighbor noise! Just woods, fields and creeks and all their critters. Good place to write, read and rest. No screens. Best for a small family, close friends or a couple. Not much privacy amongst the guests, but very private from the rest of the world! My husband and I loved it and hope to return!"
Awesome private off grid cabin with creek view.
Inviting Waterfront Cottage on Cedar Creek
Property grounds
Inviting Waterfront Cottage on Cedar Creek
10.0 out of 10, Exceptional, 26 reviews
"Lovely home with a beautiful waterview. Perfect base for exploring Tangier Island and wonderful dining in Orancock. Meg is a terrific host!"
Inviting Waterfront Cottage on Cedar Creek
Charming Cottage - Ultimate Relaxation Destination
Exterior
Charming Cottage - Ultimate Relaxation Destination
10.0 out of 10, Exceptional, 109 reviews
"My friend were doing a girl's trip and needed a place near the Tangier Island ferry. We got so much more! This house is in a great location...3 minutes from the ferry and restaurants and Walmart! All of which we needed! We couldn't have asked for a better place to stay! Doris was amazing to work with as well! Thank you, Doris!"
Charming Cottage - Ultimate Relaxation Destination
Nassawadox Creek Waterfront Home with Private Pool
Outdoor pool
Nassawadox Creek Waterfront Home with Private Pool
10.0 out of 10, Exceptional, 32 reviews
"The property was as described in the listing. It was peaceful, relaxing and secluded. We traveled with our three teenage kids and dogs. The kids absolutely loved the pool and our dogs were immediately relaxed. We were able to catch blue crabs off of the dock, no luck in fishing but that was probably more us then the area. Would absolutely return to the rental. It was an amazing break from a hectic life. Thank you for sharing your place with us."
Nassawadox Creek Waterfront Home with Private Pool
Perfect Cozy Vacation Rental on the Eastern Shore
2 bedrooms, free WiFi, bed sheets
Perfect Cozy Vacation Rental on the Eastern Shore
8.4 out of 10, Very Good, 22 reviews
"Nice area, close to oyster Bay boat ramp. Easy spot to park boat"
Perfect Cozy Vacation Rental on the Eastern Shore
This is the NO DRAMA ZONE you have been looking for! Come relax and HAVE FUN!
On the beach, sun loungers
This is the NO DRAMA ZONE you have been looking for! Come relax and HAVE FUN!
10.0 out of 10, Exceptional, 152 reviews
"Relaxing on a private beach, kayaks, fishing, bonfires, s'mores, making new friends, the list could go on and on. The host was attentive and energetic. Every request was met with a speedy solution. Our puppy, Eva, had the time of her life. If you are looking for quiet spot to relax and have fun then look no further! This is the perfect spot with endless possibilities."
This is the NO DRAMA ZONE you have been looking for! Come relax and HAVE FUN!
Pet Friendly Tiny Livin 3min from Cape Charles
Beach nearby
Pet Friendly Tiny Livin 3min from Cape Charles
10.0 out of 10, Exceptional, 7 reviews
"We celebrated our anniversary in Cape Charles for a week and stayed in the “Fisherman” unit. The property and home itself were well maintained and cared for. We enjoyed tiny livin for the week and would definitely do it again and recommend it to anyone marking a trip to the eastern shore. It may not be directly in the heart of Cape Charles like other properties but that is completely fine, the “community” feel definitely makes up for it. Eric & Sylvia we’re excellent people as well. I really...
The price is $258
$408 total
includes taxes & fees
Jun 23 - Jun 24
Pet Friendly Tiny Livin 3min from Cape Charles
Smith Beach Pines - Waterfront, Pet friendly, private dock!
Property grounds
Smith Beach Pines - Waterfront, Pet friendly, private dock!
10.0 out of 10, Exceptional, 2 reviews
"Cute, clean house in a very quiet neighborhood (in December)"
Smith Beach Pines - Waterfront, Pet friendly, private dock!
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.
Fridge, microwave, oven, stovetop
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.
10.0 out of 10, Exceptional, 2 reviews
"Last minute trip for a family funeral. This was a wonderful addition to my stay on the Eastern Shore because I was close to my church, family and friends but the property was everything a vacation should be! Excellent Home and yard space! A place of peace and serenity! Beautiful Home and Attentive Property Manager! Loved our time!"
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.
Sunflower Cottage - Waterfront; Outdoor shower!
Beach
Sunflower Cottage - Waterfront; Outdoor shower!
10.0 out of 10, Exceptional, 2 reviews
"The dock and view were spectacular!! The bathroom shower was tiny. We aren’t big, but a full size man would have had issues."
Sunflower Cottage - Waterfront; Outdoor shower!
Bayfront Retreat w/ Game Room + Outdoor Pool!
Lake
Bayfront Retreat w/ Game Room + Outdoor Pool!
9.8 out of 10, Exceptional, 23 reviews
"Beautiful location! Great for a family long weekend! We had a awesome time together!"
Bayfront Retreat w/ Game Room + Outdoor Pool!
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
1 bedroom, free WiFi, bed sheets
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
10.0 out of 10, Exceptional, 20 reviews
"The room was as presented. Clean and nicely appointed. Some noise from downstairs reminded us of apartment living. It would have helped to be assured that there was no way to get from ground level apartment to the upstairs apartment from inside."
The price is $169
$338 total
includes taxes & fees
Jun 15 - Jun 16
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
Calling all hunters, almost 33 more acres across the street used for hunting.
Game room
Calling all hunters, almost 33 more acres across the street used for hunting.
9.2 out of 10, Wonderful, 27 reviews
"This house and property are beautiful. It is very secluded and right on the water. The house was spotless when I arrived and has everything you need or want. The pool is huge. I had an awesome stay and I cannot wait until I go back in August!"
Calling all hunters, almost 33 more acres across the street used for hunting.
Charming 3-bedroom house with game room in Historic Onancock. Pet friendly
View from property
Charming 3-bedroom house with game room in Historic Onancock. Pet friendly
10.0 out of 10, Exceptional, 1 review
"The property was very clean. Had plenty of little extra things as in coffee and snacks!! All the parking was a positive plus."
Charming 3-bedroom house with game room in Historic Onancock. Pet friendly
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See all available properties in Painter
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.

Other types of properties in Painter you may be interested in

Charming Painter Home w/ Chesapeake Bay Views
Beach
Charming Painter Home w/ Chesapeake Bay Views
8.2 out of 10, Very Good, 42 reviews
"Stayed here to go fishing worked out great"
Charming Painter Home w/ Chesapeake Bay Views
Charming Painter Home w/ Chesapeake Bay Views
Interior
Charming Painter Home w/ Chesapeake Bay Views
3.0 star property
Charming Painter Home w/ Chesapeake Bay Views
Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
Beach
Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
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.

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 $169 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 Painter Home w/ Chesapeake Bay Views: Visitors like this Painter vacation home rental. It offers a fireplace, a furnished patio, and a barbecue grill to help you feel perfectly comfortable 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. You can relax into your vacation with a private yard and a selection of games.

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 North Street Market, or get out into nature at a spot like Parramore Beach. In the larger area, you’ll find The Blue Crow Antique Mall and Chatham Vineyards.

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.

Recent reviews of Painter properties
Expedia verified reviews

Quality Inn & Suites

Quality Inn & Suites

5/5 Excellent
"been staying here for years as it was convenient for us but we were not happy as it was run down and not being cared for properly. it seems the property is under new management. what a difference "
A verified traveler stayed at Quality Inn & Suites
Posted 1 day ago
Quality Inn & Suites