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Vacation Homes in Painter

Pet Friendly Tiny Livin 3min from Cape Charles

10.0 out of 10, Exceptional, (8)
"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 1,155
SAR 1,473 total
includes taxes & fees
5 Aug - 6 Aug
Pet Friendly Tiny Livin 3min from Cape Charles

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

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.

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

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

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!

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

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 Retreat- Relaxing Family Fun! King Bed, Private Dock great 4 Fishing!

10.0 out of 10, Exceptional, (1)
"Very clean beautiful home lots of room. Family oriented. Beautiful view,plentiful parking space quiet peaceful relaxing pla e to stay. Highly recommend for a wonderful vacation or getaway. "
Waterfront Retreat- Relaxing Family Fun! King Bed, Private Dock great 4 Fishing!

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

10.0 out of 10, Exceptional, (1)
"Peaceful, relaxing place with wonderful waterfront views. House is spacious and well-stocked, with a large fenced yard. We enjoyed catching fish and blue crabs right from the dock and kayaking on the river. Highly recommend. "
Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard

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 1,008
SAR 1,276 total
includes taxes & fees
27 Jul - 28 Jul
Experience Tiny Living, in Cape Charles, Va

Walk to Smith Beach: Spacious Home w/ Hot Tub

Walk to Smith Beach: Spacious Home w/ Hot Tub

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

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

10.0 out of 10, Exceptional, (57)
"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

Whimsical Tiny House, Cape Charles Virginia

9.2 out of 10, Wonderful, (14)
"We love staying in the tiny home, Eric was such a nice host"
The price is SAR 1,155
SAR 1,452 total
includes taxes & fees
6 Aug - 7 Aug
Whimsical Tiny House, Cape Charles Virginia

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

10.0 out of 10, Exceptional, (25)
"Wonderful stay and beautiful accomodations"
The price is SAR 571
SAR 1,192 total
includes taxes & fees
3 Aug - 4 Aug
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Tiny House Hideaway with King sized Bed

10.0 out of 10, Exceptional, (4)
"We absolutely enjoyed our little tiny home! The property was great and the things to do close by were great! We would definitely stay again! "
Tiny House Hideaway with King sized Bed

Spacious Cheriton Home: 8 Mi to Cape Charles!

9.8 out of 10, Exceptional, (16)
"We had the best time...the kids enjoyed the pool very much.....plenty of places to eat...and groceries near by..highly recoment..really nice vacation spot..."
Spacious Cheriton Home: 8 Mi to Cape Charles!

Chesapeake Bay Retreat Private Dock + Beach

10.0 out of 10, Exceptional, (1)
"Came to the eastern shore for a wedding-could not have found a better property or owner! Great communication, property was better than advertised—we will be back!! Thanks so much to Genevieve for being so attentive and helpful!!!"
Chesapeake Bay Retreat Private Dock + Beach

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!
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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