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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

Nassawadox Creek Waterfront Home with Private Pool
Outdoor pool

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (41)
"Had an amazing stay. The house is beautiful, plenty of space and things to do. Enjoyed swimming in the pool, being surrounded by nature and hanging out on the dock. The house had everything we needed, the neighbors were delightful. "
Nassawadox Creek Waterfront Home with Private Pool
Bayfront Retreat w/ Game Room + Outdoor Pool!
Lake

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

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

9.4 out of 10, Exceptional, (3)
Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!
Timeless Elegance with Modern Luxury: Historic 6-Bedroom Home-Newly Renovated!
View from property

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 1,238
AED 3,873 total
includes taxes & fees
9 May - 10 May
Timeless Elegance with Modern Luxury: Historic 6-Bedroom Home-Newly Renovated!
Secluded Remote Waterfront Man Cave Family Ready 2025
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Secluded Remote Waterfront Man Cave Family Ready 2025

9.4 out of 10, Exceptional, (151)
"Beautiful spot. Location location location! Can’t wait to go back"
Secluded Remote Waterfront Man Cave Family Ready 2025
your own Private beach, adjacent nature preserve-Sunset Dunes Cape Charles, VA
Miscellaneous

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
Property grounds

Inviting Waterfront Cottage on Cedar Creek

10.0 out of 10, Exceptional, (34)
"Lovely small town!"
The price is AED 642
AED 1,499 total
includes taxes & fees
22 May - 23 May
Inviting Waterfront Cottage on Cedar Creek
Experience Tiny Living, in Cape Charles, Va
Miscellaneous

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
11 May - 12 May
Experience Tiny Living, in Cape Charles, Va
Huntington Farm - Great Family Retreat
Property grounds

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.
Fridge, microwave, oven, stovetop

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!
Outdoor dining

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
Interior

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!
TV, fireplace, books

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!
TV, fireplace, books

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.
Beach

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
Terrace/patio

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
Terrace/patio

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
Beach nearby

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
11 May - 12 May
Whimsical Tiny House, Cape Charles Virginia
Whimsical Cottage with Gorgeous Views of the Bay, overlooking Russell Marina.
Exterior

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.
Game room

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.
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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Other property types in Painter

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

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
Secluded Remote Waterfront Man Cave Family Ready 2025
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Secluded Remote Waterfront Man Cave Family Ready 2025

9.4 out of 10, Exceptional, (151)
"Beautiful spot. Location location location! Can’t wait to go back"
Secluded Remote Waterfront Man Cave Family Ready 2025
Nassawadox Creek Waterfront Home with Private Pool
Outdoor pool

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (41)
"Had an amazing stay. The house is beautiful, plenty of space and things to do. Enjoyed swimming in the pool, being surrounded by nature and hanging out on the dock. The house had everything we needed, the neighbors were delightful. "
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.