Painter Vacation Rentals

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Vacation Rentals in Painter

Beach
Charming Painter Home w/ Chesapeake Bay Views
8.2 out of 10, Very Good, (42)
"Stayed here to go fishing worked out great"
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
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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Outdoor pool
Nassawadox Creek Waterfront Home with Private Pool
10.0 out of 10, Exceptional, (31)
"All girls weekend was a great success. The house was clean and comfortable. Very vintage style. The view was great."
Nassawadox Creek Waterfront Home with Private Pool
Property grounds
As close as you can get to the ocean south of Chincoteague
10.0 out of 10, Exceptional, (122)
"The house was perfect for our family’s long weekend stay in April 2024. The location is splendid for its views, water accessibility and peace and quiet. We kayaked to the barrier island (approx.15 min) and found many pristine whelk sea shells. We thoroughly enjoyed crabbing and fishing in the creek as well bird watching. The homeowners really have provided just about everything you could ask for as far as amenities and supplies. Additionally they were very helpful and informative when we had...
The price is ￥47,097
per night
Jun 16 - Jun 17
As close as you can get to the ocean south of Chincoteague
Cute and Cozy Vacation Stay on the Eastern Shore!
8.8 out of 10, Excellent, (52)
"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!
Property grounds
Inviting Waterfront Cottage on Cedar Creek
10.0 out of 10, Exceptional, (25)
"Three family groups - 5 adults and one toddler - lot of room so not on top of each other - we cooked in all weekend - nicely equipped kitchen, roomy dining table (also great for games and cards). Thoroughly enjoyed the porch room - beautiful view. Walked around the yard with the toddler - spacious. Used the kayaks - nice to have that option. Took some walks - nice area. Next door neighbor - not close, but was playing loud music while setting up for a party, a minor irritant. During the party...
Inviting Waterfront Cottage on Cedar Creek
Property grounds
Awesome private off grid cabin with creek view.
9.4 out of 10, Exceptional, (9)
"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.
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)
"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
Exterior
Charming Cottage - Ultimate Relaxation Destination
10.0 out of 10, Exceptional, (108)
"My cousin and I stayed in the cottage for a girls' weekend. We adore it! We wish we could live here forever! It is clean and comfortable and better than the photos represent. We especially love the layout and charming decor. It is very close to the quaint little town. We enjoyed lunch on the deck at Mallard's. We had lots of fun at The Blarney Stone for karaoke. We highly recommend this cottage!"
Charming Cottage - Ultimate Relaxation Destination
Fridge, microwave, stovetop, dishwasher
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
10.0 out of 10, Exceptional, (1)
"I knew instantly that this was the place for our group of 10! Lots of space to accommodate that many people in one area. It is a bit of a drive into Cape Charles, but it is worth it! Highly recommend this house!"
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
1 bedroom, iron/ironing board, free WiFi, bed sheets
Tiny House Hideaway with King sized Bed
10.0 out of 10, Exceptional, (1)
"So comfortable and Nice. Perfect"
The price is ￥30,519
per night
May 29 - May 30
Tiny House Hideaway with King sized Bed
1 bedroom, free WiFi, bed sheets
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
10.0 out of 10, Exceptional, (20)
"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 ￥26,519
per night
May 29 - May 30
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
Property grounds
Smith Beach Pines - Waterfront, Pet friendly, private dock!
10.0 out of 10, Exceptional, (2)
"Cute, clean house in a very quiet neighborhood (in December)"
Smith Beach Pines - Waterfront, Pet friendly, private dock!
Game room
Calling all hunters, almost 33 more acres across the street used for hunting.
9.0 out of 10, Wonderful, (26)
"The Clifton House is like stepping into your own manor by the bay. The large 5-acre property ensures privacy and peace. Upon our arrival, the home was clean and the furniture in good condition. The house is LARGE with room for everyone in our party of 8 to spread out and relax. For 6 guests in our party, this was their second stay at the Clifton House, and they all said it was as wonderful as they all remembered. All the rooms boast gorgeous views and lots of light from the numerous windows....
Calling all hunters, almost 33 more acres across the street used for hunting.
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)
"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.
Beach
Sunflower Cottage - Waterfront; Outdoor shower!
10.0 out of 10, Exceptional, (2)
"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!
Lake
Bayfront Retreat w/ Game Room + Outdoor Pool!
9.8 out of 10, Exceptional, (23)
"Beautiful location! Great for a family long weekend! We had a awesome time together!"
Bayfront Retreat w/ Game Room + Outdoor Pool!
View from property
Charming 3-bedroom house with game room in Historic Onancock. Pet friendly
10.0 out of 10, Exceptional, (1)
"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
2 bedrooms, free WiFi, bed sheets
Perfect Cozy Vacation Rental on the Eastern Shore
8.4 out of 10, Very Good, (22)
"Nice area, close to oyster Bay boat ramp. Easy spot to park boat"
Perfect Cozy Vacation Rental on the Eastern Shore
Don't see what you're looking for?
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

Beach
Charming Painter Home w/ Chesapeake Bay Views
8.2 out of 10, Very Good, (42)
"Stayed here to go fishing worked out great"
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
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.

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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?

Charming Painter Home w/ Chesapeake Bay Views: Visitors like this Painter vacation home rental. It offers a fireplace, a 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 garden 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

Awesome private off grid cabin with creek view.

Awesome private off grid cabin with creek view.

5/5 Excellent
Peaceful cabin
"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."
A verified traveler stayed at Awesome private off grid cabin with creek view.
Posted 4 days ago
Awesome private off grid cabin with creek view.