Vacation rentals in Cheriton

Guesthouse at Vessel Farm & Winery, Waterfront

Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Oyster Cottage - Seaside View

Relax at this unique and tranquil historic waterfront cottage on the seaside of the Eastern Shore of Virginia. Experience sunrises and moonrises over the marsh and sunsets over the Oyster Harbor from almost every room in the house. Close to all that CAPE CHARLES has to offer but a world away - just 15 minutes from restaurants, public beaches and shops. An original turn of the century Fishermans' cottage that was completely restored in 2024 by Architect/designer owner. Sorry no pets allowed

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.

Chesapeake Shore Cottage: Private Beach w/Kayaks

Bayside Getaway on the Chesapeake in Port Haywood: Steps to the Sand! Welcome to your perfect coastal escape! Nestled right on the tranquil shores of the Chesapeake Bay in beautiful Port Haywood, Virginia, this charming beachfront cottage offers the ultimate blend of secluded relaxation and small-town convenience. Whether you’re sipping your morning coffee on the porch as the sunrises over the water or launching a kayak for an afternoon adventure, this is the place where memories are made.

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

3 Blocks to Beach, Fenced yard, Historic District!

Welcome to Peach Haven, a newly renovated duplex in the Cape Charles historic district. Just 1 block from the park and 3 blocks from the beach, it's the ideal base for your Cape Charles escape. This pet-friendly rental sleeps five guests comfortably with a master bedroom (queen bed) and a second bedroom with a custom-made full-over-full bunkbed. The house has been thoughtfully stocked with everything you'll need for a comfortable stay. Need more space? Ask about renting the other side, too!

1903 By the Sea - Minutes from Cape Charles

Our spacious American foursquare style home built in 1903 is the perfect family retreat! Located in quaint Cheriton, we are a quick 8 minute drive to downtown Cape Charles, and a 7 minute drive to the boat ramp in Oyster. It's the perfect location for both the fisherman and the beachgoer! We renovated the kitchen & bathrooms while leaving the original hardwood floors, wooden elements and layout of the house the same to preserve the character of this 118 year old roomy home. On 1.25 acres!

The Cheriton Shed

The guesthouse, a converted tractor shed, sits on its own (mostly) private acre behind the host family residence. It is located in the quiet town of Cheriton, just three miles from the restaurants and beachfront of downtown Cape Charles. Tucked into the edge of the woods and with an unobstructed view of the night sky, "The Shed" offers the kind of quiet found only in the country. Bring bikes, explore our natural wildlife, and taste-test Cheriton’s not one, but two famous taco joints.

Coastal Red Barn Retreat

Located on the coastal seaside of Cape Charles, this barn was originally built in 1893. It has been lovingly restored to reflect the area's rich history, while providing modern comforts for today's guests. The Red Barn is nestled in the midst of scenic farmland, yet is only a few miles from the charming downtown, with its eclectic restaurants and unique shops. Enjoy the fresh breezes of the Atlantic and watch the sunrise over the fields from the comfort of the barn's private deck.

Chesapeake Retreat - Bay view

You’ll love my place because of the Chesapeake Bay views, the ambiance, the outdoors space, and the location. Chesapeake Retreat is located less than a 5-minute drive from downtown Cape Charles, the Cape Charles beach, the grocery store, restaurants, shops, and galleries. Cape Charles and the Eastern Shore are wonderful to explore. Sporting enthusiasts can golf, kayak, go horseback riding, and enjoy bird watching. The Chesapeake Retreat is a completely smoke-free residence.

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.

"Live Life Sunnyside Up" - Minutes From The Beach!

Welcome to "Live Life Sunnyside Up" on the Shore! Take a trip off the busy beaten path and kick your feet up at our little slice of paradise. Kid friendly with plenty of amenties for you and your family. On a quiet street, less than 4 miles from the historic town of cape charles and beach, get ready to take a load off and enjoy the many treasures Cape Charles has to offer! Just 5 short minutes from the Oyster Boat Ramp, fishermen are sure to find their honey hole here!