Painter Holiday Rentals

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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, (53)
"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, (26)
"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, (15)
"Hubs and I were looking for a relaxing getaway and boy did we find it. This cottage was perfect. "
The price is NZ$447
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, (23)
"Great place."
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 8, and is pet friendly.

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

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (119)
"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

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.

NEW! Oyster Cottage in Historic Fishing Village

10.0 out of 10, Exceptional, (2)
"My family and I just loved staying in Oyster Cottage! It is a lovely space and the views from the deck were wonderful! We really enjoyed venturing out to tour Cape Charles and Chincoteague and then return home to this comforting place. "
NEW! Oyster Cottage in Historic Fishing Village

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$476
includes taxes & fees
1 Sept - 2 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 NZ$467
includes taxes & fees
1 Sept - 2 Sept
Pet Friendly Tiny Livin 3min from Cape Charles

Virginia Landing RV Campground

2.0 star property
8.0 out of 10, Very good, (36)
The price is NZ$292
includes taxes & fees
15 Sept - 16 Sept
Virginia Landing RV Campground

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

10.0 out of 10, Exceptional, (57)
" We looked at many properties that were on the water, secluded, and pet friendly. No other option came close. Zero city. All views, stars, water, peace and quiet. Complete with full wrap around fence for the dogs to roam free. Perfect off season location to relax and recharge. Host was easily reachable and we had zero issues. The view from the master bedroom is incomparable. "
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

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

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!

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
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

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?

Pet Friendly Tiny Livin 3min from Cape Charles: This holiday home rental outside of Painter is located in a rural location, and offers a BBQ, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

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.