Vacation rentals in Painter

Newly Constructed 2nd-Story Studio Apartment

Our guests can't say enough & pictures just don't do it justice! From the luxury linens & complimentary amenities, we have tried to think of everything! Enjoy a quiet get-a-way just for two or relax with the whole family at this beautiful, newly constructed home located 1/4 mile off Route 13 & less than an hour from area beaches. There are two units with separate outside entrances, but they can be rented together if you need more space. This listing is for the upstairs open studio apartment.

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Camp Belle Haven

Save now! Welcome to Camp Belle Haven, a vacation rental alternative to Cape Charles. Relax with the whole family at this peaceful waterfront getaway in Northampton County on the Eastern Shore of Virginia. The owners are opening camp to non-family campers. Enjoy assorted water activities with only two neighbors on this private road outside of Exmore. Close enough to enjoy day trips to Cape Charles and Chincoteague. Enjoy the charming towns then escape the crowds to your private retreat.

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

The Waverly Treehouse

Reconnect with nature and sway with the trees in this rustic treehouse nestled away in the woods with a gorgeous view of Hungar's creek. Enjoy the view from the front porch or while relaxing around the fire pit. Visit the adorable beach town of Cape Charles, complete with a beautiful beach, brewery, distillery and plenty of restaurant options, or stop by the nearby vineyard for some local wine. Usage of dock, kayaks, grill, and fire pit all included. Beach towels and cooler also provided.

Private Country Beach Retreat

Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

Holly Cove’s “Tiny” Guesthouse

Rest and relax at our guesthouse with magnificent views of Onancock Creek. The guesthouse is small and has one bedroom w/ queen bed, bathroom, refrigerator, microwave, coffee maker, brick patio, outdoor fire pit, WiFi, Smart TV, private entrance, and dock. From the dock you can fish, swim, and kayak. Only a 5 minute drive to enjoy the historic town of Onancock, VA. We also rent “The Suite at Holly Cove” and it has more living space. This rental is available through Airbnb as well.

Stargazer Tiny Cabin

(Winter: Stargazer has a diesel heater and a woodstove but is not insulated. The cabin can be kept quite warm into the low 30's if these heaters are running. Below freezing may freeze pipes, message for info) Rustic off grid tiny cabin tucked in the trees on the back side of a large field. The cabin has solar, kitchenette, shower, composting bathroom, heat, and Wifi! Enjoy being immersed in nature while staying comfortable in a quirky cabin built from local and reclaimed materials.

Serenity Manor 1BR Private Historic Home First Flr

Stay in a charming 1883 Victorian home, just a 10-minute walk to downtown Onancock’s shops, restaurants, and wharf. This private garden-level retreat offers exclusive access to Serenity Manor’s first floor, including a king bedroom, spacious living areas, full kitchen, screened porch, and large backyard. Enjoy modern comforts like 4K TVs, high-speed internet, USB charging, plus a futon, sleeper sofa, and washer/dryer—perfect for couples or solo travelers seeking space and charm.

Egret’s Point on the Creek

Egrets Point on the Creek, is a beautiful and peaceful place to relax and plan your Eastern Shore exploration. Whether you are enjoying the fire pit by the creek, or taking a nap in the hammocks, canoeing, walking or exploring historic Onancock, life by the creek is sweet. Chincoteague to the north, Cape Charles to the south. Excitement abounds. Coastal exploration, boating, fishing, fine dining, artisan shops, art galleries, farmers markets and sandy beaches. Come and enjoy!

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Luxe 2BR Cabin w/ Deck + Creek View | Working Farm

At this gorgeous creekside cabin you’ll reconnect with pastoral Virginia in calm and comfort. Watch deer graze from the decks, grill dinner and gather around the fire pit, or head into nearby Onancock for seafood and boutiques. Inside, wood-clad interiors and minimalist modern design come with floor-to-ceiling views and fast WiFi (for travelers who need to mix work and play). A restful home base with walking paths, quiet mornings, and starry skies—just minutes from town.