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Compare 59 Vacation Homes in Painter with updated reviews, rates, and availability.

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

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (39)
"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

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

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 503
AED 922 total
includes taxes & fees
26 Jan - 27 Jan
Experience Tiny Living, in Cape Charles, Va

Thomas Inn Q 6 miles from Cape Charles - double room

6.0 out of 10, (2)
"Old house well maintained excellent guest best experience "
Thomas Inn Q 6 miles from Cape Charles - double room

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball in Onancock

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball in Onancock

Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

9.4 out of 10, Exceptional, (151)
"This was exactly what I was looking for. The Property is very private and the yard surrounding the house was huge. I found it comfortable and cozy. Randy was very accommodating and asked that you respected his property and clean up after yourself and your pets which is to be expected were I come from, a small ask. He had plenty to offer. The private dock and water access was perfect and being able to us his canoes and kayaks was a very nice extra. One of my favorite things was the very large...
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

Counting Corks - Waterfront, Pet friendly, private dock!

10.0 out of 10, Exceptional, (5)
"Everything was as advertised and remarkably comfortable. Well stocked with kitchen supplies; linens and towels were clean and fresh; glasses in bar-room leading to deck and deck were both lovely for morning coffee and evening wine"
Counting Corks - Waterfront, Pet friendly, private dock!

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

10.0 out of 10, Exceptional, (18)
"Even though we were there off-season for a wedding, this VRBO is super close to the beach. Also close is a grocery store. Only possible issue is a super squeaky floor in master bedroom could disturb a light sleeper or a baby. Kitchen is masterfully stocked, great deck, quiet neighborhood, awesome water pressure (although you may prefer bottled water due to the minerals). You'll need to bring your own shampoo as well. It was perfect for our needs and super cute!"
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.

Bayfront Retreat w/ Game Room + Outdoor Pool!

9.8 out of 10, Exceptional, (32)
"Our second time staying at the house. We absolutely love the property and all its surrounding wildlife. Enjoyed spending time hiking, fishing, crabbing, and watching eagles flying over the water. The house is clean and well stocked, and the game room is a great place to spend time in the evenings or rainy days. The hosts are attentive and helpful. Looking forward to visiting again!"
Bayfront Retreat w/ Game Room + Outdoor Pool!

Whimsical Tiny House, Cape Charles Virginia

9.4 out of 10, Exceptional, (12)
"We love staying in the tiny home, Eric was such a nice host"
The price is AED 539
AED 966 total
includes taxes & fees
26 Jan - 27 Jan
Whimsical Tiny House, Cape Charles Virginia

Secluded Seaside Village Retreat in Fishing Town

9.8 out of 10, Exceptional, (12)
"This is such a sweet home in a great neighborhood. We came up for a short fishing trip in the bay and were so happy with the location and the house. The property is close to restaurants, grocery stores, and boat launches. It is an older home, so it does have a few quirks but overall has everything needed for a comfortable stay. I can’t say enough good things about the owner. He is so kind and responsive which made our trip that much more enjoyable. "
Secluded Seaside Village Retreat in Fishing Town

Charming Painter Home w/ Chesapeake Bay Views

8.2 out of 10, Very Good, (43)
"Stayed here to go fishing worked out great"
Charming Painter Home w/ Chesapeake Bay Views

Pet Friendly Tiny Livin 3min from Cape Charles

10.0 out of 10, Exceptional, (7)
"We celebrated our anniversary in Cape Charles for a week and stayed in the “Fisherman” unit. The property and home itself were well maintained and cared for. We enjoyed tiny livin for the week and would definitely do it again and recommend it to anyone marking a trip to the eastern shore. It may not be directly in the heart of Cape Charles like other properties but that is completely fine, the “community” feel definitely makes up for it. Eric & Sylvia we’re excellent people as well. I really...
The price is AED 539
AED 966 total
includes taxes & fees
26 Jan - 27 Jan
Pet Friendly Tiny Livin 3min from Cape Charles

Luxury Beachfront 5 Bedroom, 3.5 Bath home with 200 ft. of PRIVATE BEACH!

9.8 out of 10, Exceptional, (34)
"This was my family's 4th time staying at the Sand Castle so I don't have much to add since my previous reviews. We did not notice that the listing had changed since we had booked and were sorry to see that the bunkbeds had been removed but we worked things out. Also the beach has changed quite a bit and the sand disappears completely at high tide now. This is obviously not related to VRBO or the homeowner, just something future renters may want to know. We still had a good time, we just had to...
Luxury Beachfront 5 Bedroom, 3.5 Bath home with 200 ft. of PRIVATE BEACH!

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

Home on Chesapeake Bay: Large Yard, Fire Pit

9.0 out of 10, Wonderful, (6)
"Very comfortable, clean and cute place with a peaceful back yard where we watched wildlife, and the neighbors adorable flock of chickens! ! Great location close to town."
Home on Chesapeake Bay: Large Yard, Fire Pit

Exquisite 4 bedroom, 3 and a half bath Georgian Estate Home on the Beach!

10.0 out of 10, Exceptional, (3)
"This house is so special. For a Northeast city girl, this was the quintessential Southern home looking out right on the bay. Its beautiful wrap-around porches and outdoor seating areas hit the spot. And the sunsets....wow! It's very isolated and peaceful. My family and I enjoyed it immensely, getting to Cape Charles (a super cute town) was a bit of a drive but it was very nice to leave the compound! The house was clean, had an open floor plan and the kitchen was well stocked (all appliances and...
Exquisite 4 bedroom, 3 and a half bath Georgian Estate Home on the Beach!

Inviting Waterfront Cottage on Cedar Creek

10.0 out of 10, Exceptional, (34)
"Lovely small town!"
Inviting Waterfront Cottage on Cedar Creek

Restored 1930’s Tiny Home 3 min to Cape Charles

Restored 1930’s Tiny Home 3 min to Cape Charles
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

Charming Painter Home w/ Chesapeake Bay Views

8.2 out of 10, Very Good, (43)
"Stayed here to go fishing worked out great"
Charming Painter Home w/ Chesapeake Bay Views

Charming Painter Home w/ Chesapeake Bay Views

3.0 star property
8.0 out of 10, Very Good, (1)
Charming Painter Home w/ Chesapeake Bay Views

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
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.