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

Compare 71 Vacation Homes in Painter with updated reviews, rates, and availability.

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!

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 SAR 673
SAR 3,212 total
includes taxes & fees
24 Mar - 25 Mar
Timeless Elegance with Modern Luxury: Historic 6-Bedroom Home-Newly Renovated!

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!

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.

Inviting Waterfront Cottage on Cedar Creek

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

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 841
SAR 1,051 total
includes taxes & fees
27 Mar - 28 Mar
Experience Tiny Living, in Cape Charles, Va

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

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

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.

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!

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!

9.8 out of 10, Exceptional, (11)
"You turn on their driveway and it’s lined with beautiful trees all the way down to the beautiful home! The endless landscaping, flowers, trees, bushes not to mention sitting areas outside everywhere! The inside so spacious perfect for families! Not to worry about bedrooms or baths there is plenty! Outside swings and toys for kids, ping pong table, golf enthusiast can hit the balls right in the yard, foosball, hammock swings, lounges and so many patios and endless grills for bbq gatherings! Then...
Spacious Cheriton Home: 8 Mi to Cape Charles!

your own Private beach, adjacent nature preserve-Sunset Dunes Cape Charles, VA

10.0 out of 10, Exceptional, (20)
"Where to even begin with Sunset Dunes? My wife and I chose this rental to celebrate our 10 year wedding anniversary and we couldnt be more happy with that choice. Its overwhelming to even begin describing how amazing this property is. Form the beautiful beach to the amazing forest and the incredible house that ties it all together. We've stayed at a lot of places all around Virginia and Sunset Dunes is by far the best we have ever stayed at before. Lots of places to explore or if you want you...
your own Private beach, adjacent nature preserve-Sunset Dunes Cape Charles, VA

Virginia Retreat w/ Porch & Grill, Near Beaches!

10.0 out of 10, Exceptional, (5)
"We visited my dad for his birthday. We know the area well and enjoyed our stay. "
Virginia Retreat w/ Porch & Grill, Near Beaches!

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 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

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.

Waterfront, Gorgeous 4 BDR, 3 BA Beautiful views & sunsets

10.0 out of 10, Exceptional, (4)
"Waterfront house with All the ameneiies!! Breathtaking View from every room of house!! Homely feeling!"
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.
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

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

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
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.