Search Vacation Homes in Painter

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 58 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

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

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

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 937 total
includes taxes & fees
24 Feb - 25 Feb
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

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

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 981 total
includes taxes & fees
24 Feb - 25 Feb
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

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!

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

9.0 out of 10, Wonderful, (2)
Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!

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!

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

10.0 out of 10, Exceptional, (4)
"We stayed to do a fishing tour in the bay, and it was perfect. It was extremely clean, and we loved the layout. It had plenty of space for our family. It has a nice dock and a fire pit in the backyard. Overall, there are only good things to say about this property. If you are planning a visit to the area, it is well worth it!"
Waterfront family home with great views, full kitchen, & strong Wi-Fi.

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.

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 559
AED 3,019 total
includes taxes & fees
4 Mar - 5 Mar
Timeless Elegance with Modern Luxury: Historic 6-Bedroom Home-Newly Renovated!

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.

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 981 total
includes taxes & fees
24 Feb - 25 Feb
Pet Friendly Tiny Livin 3min from Cape Charles

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.

Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

10.0 out of 10, Exceptional, (1)
"This was a great stay, we loved everything about it. Highly recommended. We will definitely return."
The price is AED 516
AED 951 total
includes taxes & fees
2 Mar - 3 Mar
Hippie Hideaway - Tiny House w/ Fire Pit & BBQ
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

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

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

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!
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.