Holiday Rentals in Painter

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Holiday Rentals in Painter

Our top choices for Painter holiday 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, (56)
"We had everything we needed. A very quiet, relaxing weekend. "
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

Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

10.0 out of 10, Exceptional, (16)
"Hubs and I were looking for a relaxing getaway and boy did we find it. This cottage was perfect. "
The price is €236
includes taxes & fees
1 Sept - 2 Sept
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

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

10.0 out of 10, Exceptional, (24)
"Great place."
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, (120)
"I had stayed at this property in the past and was really glad to get to stay again. It is clean, quiet, and close to the town center of Onancock. Really looking forward to returning!"
Charming Cottage - Ultimate Relaxation Destination

Remote Secluded Waterfront Estate OPEN for Chincoteague Pony Week. Only 37 Mi

9.2 out of 10, Wonderful, (156)
"Beautiful spot. Location location location! Can’t wait to go back"
Remote Secluded Waterfront Estate OPEN for Chincoteague Pony Week. Only 37 Mi

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

9.6 out of 10, Exceptional, (22)
"Perfect base to go out and explore and fish the Chesapeake. "
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

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 €244
includes taxes & fees
8 Sept - 9 Sept
Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

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, (8)
"We booked this tiny house for a spontaneous night away to do some fishing in Cape Charles. The property and house were absolutely adorable and the accommodations were exactly what we needed for a weekend away. The property had an amazing bonfire pit and grill if you don’t want to eat out, and there’s plenty of space with a fence and grassy areas if you’re traveling with a dog. The owners were extremely communicative and even went to the trouble of mailing us back something we left. We would...
The price is €241
includes taxes & fees
4 Sept - 5 Sept
Pet Friendly Tiny Livin 3min 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

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

10.0 out of 10, Exceptional, (57)
"First, the house is clean, well-stocked with the comforts of home, and architecturally stunning in a classic/traditional way. The sunsets are amazing. The breezes off the bay are refreshing. The whole property has a sense of peace. As a young man, I grew up fishing the many lakes, bays and marshlands of Louisiana …. also I worked and played on my grandfather’s farm in Virginia. This plays combines the two, magnificently. My wife, our two young boys, and the dog were at ease in this wonderful...
Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

Inviting Waterfront Cottage on Cedar Creek

10.0 out of 10, Exceptional, (37)
"We had a wonderful stay. We enjoyed the kayaks and the firepit as well as a few local restaurants. The house was clean and the host was very responsive. "
Inviting Waterfront Cottage on Cedar Creek

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

Counting Corks - Waterfront, Pet friendly, private dock!

10.0 out of 10, Exceptional, (8)
"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!

Awesome private off grid cabin with creek view.

9.8 out of 10, Exceptional, (16)
"Beautiful slice of heaven on the creek. Lots of wildlife and close enough to downtown that you can have a nice night out or just light a fire and enjoy nature."
Awesome private off grid cabin with creek view.

Waterfront Retreat- Relaxing Family Fun! King Bed, Private Dock great 4 Fishing!

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. "
Waterfront Retreat- Relaxing Family Fun! King Bed, Private Dock great 4 Fishing!

Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!

9.4 out of 10, Exceptional, (6)
"The property was perfect for a very relaxing weekend. The house was exactly what we needed for our little group."
Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!
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

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, apart-hotels, 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 €236 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.