Search Vacation Homes in Painter

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 72 Vacation Homes in Painter with updated reviews, rates, and availability.

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (41)
"This is a beautiful house and Nancy is an outstanding host. We enjoyed sitting by the pool and birdwatching. My wife wanted to take the scenic main room home with us. "
Nassawadox Creek Waterfront Home with Private Pool

Bayfront Retreat w/ Game Room + Outdoor Pool!

9.8 out of 10, Exceptional, (32)
"Had a great time. Beautiful home with everything you could need. Pool kayak and pool table was very nice to have. Very private but close enough to drive to other areas for fun. "
Bayfront Retreat w/ Game Room + Outdoor Pool!

Timeless Elegance with Modern Luxury: Historic 6-Bedroom Home-Newly Renovated!

10.0 out of 10, Exceptional, (1)
"This location worked well for our large group which comprised of 3 generations. The historic style of the home works well with the renovations which include strong WiFi, new appliances and plenty of high-tech flat screen televisions. The area was very quiet and near plenty of shopping locations. This was the perfect home for family time and bonding. The host was responsive to our questions and requests. We definitely plan to stay here again! Thanks, Steve! Your home was perfect for our...
The price is AED 1,047
AED 3,635 total
includes taxes & fees
6 May - 7 May
Timeless Elegance with Modern Luxury: Historic 6-Bedroom Home-Newly Renovated!

Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

9.4 out of 10, Exceptional, (151)
"The property was secluded and relaxing. If you wanted to be active, there are opportunities on the water, or on the land. Great place to relax and enjoy nature. The house is full of interesting collectibles. The host was very helpful and attentive to guest needs."
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

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

Inviting Waterfront Cottage on Cedar Creek

10.0 out of 10, Exceptional, (34)
"Lovely small town!"
The price is AED 685
AED 1,550 total
includes taxes & fees
22 May - 23 May
Inviting Waterfront Cottage on Cedar Creek

Experience Tiny Living, in Cape Charles, Va

10.0 out of 10, Exceptional, (1)
"Adorable tiny livin…. The entire property is just quaint and cozy!"
The price is AED 777
AED 989 total
includes taxes & fees
27 Apr - 28 Apr
Experience Tiny Living, in Cape Charles, Va

Huntington Farm - Great Family Retreat

9.6 out of 10, Exceptional, (54)
"Great place to stay and beautiful views. Was perfect for our group. Highly recommend!"
Huntington Farm - Great Family Retreat

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

10.0 out of 10, Exceptional, (18)
"Great place."
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.

Counting Corks - Waterfront, Pet friendly, private dock!

10.0 out of 10, Exceptional, (5)
"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!

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

10.0 out of 10, Exceptional, (4)
"We had a great time and stay at this property!! Would love to stay here again!"
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Spacious Cheriton Home: 8 Mi to Cape Charles!

9.8 out of 10, Exceptional, (12)
"Would absolutely stay again. We had a large group of women for a ladies weekend and so much fun was had. From singing on the porch, to watching sunsets and the tide to enjoying the beautiful grounds. We had a few hiccups the first day but Whitney was great and we got them resolved rather quickly. I would 100% stay here again!"
Spacious Cheriton Home: 8 Mi to Cape Charles!

Virginia Retreat w/ Porch & Grill, Near Beaches!

10.0 out of 10, Exceptional, (5)
"Wonderful hosts!"
Virginia Retreat w/ Porch & Grill, Near Beaches!

Tangier Island three bedroom house near the beach.

10.0 out of 10, Exceptional, (1)
"I booked 2 nights with my parents and grandparents at the island girl getaway. It was possibly the best beach experience I’ve had yet. Tangier is an incredible island rich with history and certainly worth a visit. We enjoyed the close proximity to the beach and the caretaker, Andy was very helpful and kind. We happened to come to the island when the tides were unusually high occasionally throughout the day, yet I would note that our house seemed to be the only one which had no water near it...
Tangier Island three bedroom house near the beach.

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

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

10.0 out of 10, Exceptional, (54)
" 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

Whimsical Tiny House, Cape Charles Virginia

9.4 out of 10, Exceptional, (13)
"We love staying in the tiny home, Eric was such a nice host"
The price is AED 828
AED 1,054 total
includes taxes & fees
27 Apr - 28 Apr
Whimsical Tiny House, Cape Charles Virginia

Whimsical Cottage with Gorgeous Views of the Bay, overlooking Russell Marina.

10.0 out of 10, Exceptional, (76)
"Our family had a great time staying there for Thanksgiving. The house was charming and beautifully decorated in the style of the Eastern Shore. Plenty of space to hang out or spread out! The kids really loved the Turtle Room We would certainly stay here again!"
Whimsical Cottage with Gorgeous Views of the Bay, overlooking Russell Marina.

Calling all hunters, almost 33 more acres across the street used for hunting.

8.8 out of 10, Excellent, (28)
"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.

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

10.0 out of 10, Exceptional, (1)
"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
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.
Don't see what you're looking for?
See all available properties in Painter
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Painter

Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay

10.0 out of 10, Exceptional, (1)
"This is a wonderful property if you are looking for a nice relaxing vacation. We thoroughly enjoyed our trip."
Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (114)
"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

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (41)
"This is a beautiful house and Nancy is an outstanding host. We enjoyed sitting by the pool and birdwatching. My wife wanted to take the scenic main room home with us. "
Nassawadox Creek Waterfront Home with Private Pool
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.