Painter Vacation Rentals

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Vacation Rentals in Painter

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (50)
"We had everything we needed. A very quiet, relaxing weekend. "
Nassawadox Creek Waterfront Home with Private Pool

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

10.0 out of 10, Exceptional, (11)
"The place is amazing. The pictures on the site do not do the property justice as it is absolutely amazing. Can’t wait to stay there again."
The price is CA $278
CA $416 total
includes taxes & fees
Aug 1 - Aug 2
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

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

9.4 out of 10, Exceptional, (20)
"Perfect base to go out and explore and fish the Chesapeake. "
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

Perfect Cozy Vacation Rental on the Eastern Shore

8.2 out of 10, Very good, (23)
"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

Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.

10.0 out of 10, Exceptional, (22)
"Great place."
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.

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

9.2 out of 10, Wonderful, (155)
"Beautiful spot. Location location location! Can’t wait to go back"
Remote Secluded Waterfront Estate OPEN for Chincoteague Pony Week. Only 37 Mi

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

10.0 out of 10, Exceptional, (5)
"We had a great time and stay at this property!! Would love to stay here again!"
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Stately historic 3bdr shore house near Cape Charles, boat parking, pet friendly

10.0 out of 10, Exceptional, (2)
"This is a beautiful property! You can feel the history, it had me time traveling as I sunk into beachy stories I imagined while staying here. A wonderful place to make memories with the family 🤗 and only a 7 min drive to the Cape Charles beach! I would absolutely stay here again, honestly- I would live here if I could!! -Brianna"
Stately historic 3bdr shore house near Cape Charles, boat parking, pet friendly

Counting Corks - Waterfront, Pet friendly, private dock!

10.0 out of 10, Exceptional, (7)
"Smith Beach is small and beautiful so the area is very quiet and relaxing. Nice house with dock and the Florida room was cool! We really enjoyed crabbing right out back. "
Counting Corks - Waterfront, Pet friendly, private dock!

NEW! Oyster Cottage in Historic Fishing Village

NEW! Oyster Cottage in Historic Fishing Village

Awesome private off grid cabin with creek view.

9.6 out of 10, Exceptional, (14)
"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 Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

10.0 out of 10, Exceptional, (56)
"What an amazing home and property!! We just returned from a great stay and cant say enough about this gorgeous house! From the beautiful decor, well stocked kitchen, barn full of toys, there isnt a thing that was overlooked by the owners! Cant wait to return!"
Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

Bayfront Retreat w/ Game Room + Outdoor Pool!

9.8 out of 10, Exceptional, (36)
"Beautiful location! Great for a family long weekend! We had a awesome time together!"
Bayfront Retreat w/ Game Room + Outdoor Pool!

1903 By the Sea - Minutes from Cape Charles

2.0 star property
9.0 out of 10, Wonderful, (2)
"small town pretty quiet, quick drive to cape charles main street."
1903 By the Sea - Minutes from Cape Charles

Virginia Landing RV Campground

2.0 star property
8.0 out of 10, Very good, (35)
The price is CA $222
CA $245 total
includes taxes & fees
Jul 23 - Jul 24
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

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

Have fun with the whole family!

2.0 star property
Have fun with the whole family!

Beach Bettie's - Serene, charming cottage located on the Chesapeake Bay!

Beach Bettie's - Serene, charming cottage located on the Chesapeake Bay!

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (118)
"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
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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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?

Pet Friendly Tiny Livin 3min from Cape Charles: Visitors like this Painter vacation home rental. It is located in a rural location and offers a barbecue grill, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

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 Northampton Shopping Center.

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.