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Vacation Homes in Painter

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (44)
"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

Remote Secluded Waterfront Estate JUNE 1 - 12TH OPEN FOR RENT

9.4 out of 10, Exceptional, (153)
"Beautiful spot. Location location location! Can’t wait to go back"
Remote Secluded Waterfront Estate JUNE 1 - 12TH OPEN FOR RENT

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

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

9.2 out of 10, Wonderful, (5)
Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!

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

10.0 out of 10, Exceptional, (2)
"Great accommodations for a large group of adults with lots of king and queen sized beds, each room well appointed. Really enjoyed the high ceilings and overall spaciousness. "
Timeless Elegance with Modern Luxury: Historic 6-Bedroom Home-Newly Renovated!

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

10.0 out of 10, Exceptional, (55)
" 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

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard

1903 By the Sea - Minutes from Cape Charles

2.0 star property
8.0 out of 10, Very Good, (1)
"small town pretty quiet, quick drive to cape charles main street."
1903 By the Sea - Minutes from Cape Charles

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.

Waterfront family home with great views, full kitchen, & strong Wi-Fi.

10.0 out of 10, Exceptional, (4)
"Your place is beautiful! We had a great time! We will book again soon! "
Waterfront family home with great views, full kitchen, & strong Wi-Fi.

Home w/ Fire Pit < 1 Mi to Willis Wharf Boat Ramp!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great house for family or friends gathering. Large kitchen, great for cooking fo"
Home w/ Fire Pit < 1 Mi to Willis Wharf Boat Ramp!

Thomas Inn Q 6 miles from Cape Charles - queen room

Thomas Inn Q 6 miles from Cape Charles - queen room

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 SAR 990
SAR 1,263 total
includes taxes & fees
9 Jun - 10 Jun
Experience Tiny Living, in Cape Charles, Va

Walk to Wilkins Beach: Spacious Home w/ Hot Tub

Walk to Wilkins Beach: Spacious Home w/ Hot Tub

Counting Corks - Waterfront, Pet friendly, private dock!

10.0 out of 10, Exceptional, (6)
"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!

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 SAR 1,029
SAR 1,311 total
includes taxes & fees
11 Jun - 12 Jun
Whimsical Tiny House, Cape Charles Virginia

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.

Pet Friendly Tiny Livin 3min from Cape Charles

10.0 out of 10, Exceptional, (7)
"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 SAR 1,029
SAR 1,311 total
includes taxes & fees
9 Jun - 10 Jun
Pet Friendly Tiny Livin 3min from Cape Charles

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!

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
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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