Holiday rentals in Oyster

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Top-rated holiday rentals in Oyster

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Top guest favourite

The spacious kitchen features a large island with seating for six, modern appliances, and ample counter space. A bright window above the sink offers views of the surrounding landscape, while soft lighting complements the contemporary design. Light wood flooring enhances the welcoming atmosphere.

Farm stay in Cape Charles

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.

ValueFamilyAmenities

5.0 out of 5 average rating, 438 reviews

Top guest favourite

The exterior of the home is shown, featuring a welcoming porch with ornate detailing and a pair of rocking chairs. Lush greenery, including bushes and flowers, enhances the inviting atmosphere. The blue siding and white trim reflect the home's historic charm.

Home in Cape Charles

Bayside Bonanza | Off-street Parking | EV Charger

"Bayside Bonanza" is special. Ideally located with the main street of Cape Charles around the corner in either direction, and a 5 minute walk to the bay or Central Park. There's nothing like sitting on the front porch swing, sipping morning coffee or an evening cocktail. The home is bright and cozy, with efforts made to keep as much of the original 1890's charm as possible. We're family owned and managed, and it's our priority to help you have the most relaxing and enjoyable vacation possible!

FamilyValueKitchen

4.98 out of 5 average rating, 126 reviews

Top guest favourite

The living area features a cozy gray sofa, two armchairs, and a circular coffee table. Natural light fills the space through windows adorned with light curtains. A large wall-mounted TV is positioned above a white media console, enhancing the room's modern yet inviting aesthetic.

Townhouse in Cape Charles

Walk to Beach and Park! Outdoor shower&Fenced Yard

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 four 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. Ask about our optional golf cart rental during your stay!

ValueLocationQuiet

4.97 out of 5 average rating, 204 reviews

Top guest favourite

A serene view of the water showcases the Rappahannock River and surrounding landscape. The horizon blends various shades of blue with green grass and patches of marshland, inviting a sense of tranquility. Wisps of clouds drift across the expansive sky.

Guest house in White Stone

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

ValueFamilyIndoor spaces

5.0 out of 5 average rating, 323 reviews

Top guest favourite

Four black Adirondack chairs are positioned in a grassy area facing a tranquil body of water. Lush green reeds frame the water's edge, with a blue sky and scattered clouds above. A small dock is visible in the distance, adding to the serene setting.

Home in Belle Haven

Bay Breeze Home on private waterfront

On Virginia's beautiful Eastern Shore, the Bay Breeze Home on Occohannock Creek is the ultimate getaway for two or a large family desiring outside adventures. This 1970's spacious home has plenty of room. Experience the water with our three kayaks or family canoe and watch the abundant wildlife. Right outside your door, you may see Ospreys, Great Blue Herons, Eagles, wild ducks, porpoises, deer, geese, otters, & more. Be our guest and forget your worries in this spacious and serene spot.

LocationFamilyAir conditioning

4.98 out of 5 average rating, 163 reviews

Top guest favourite

A two-story beach house stands amidst lush greenery, featuring a spacious wrap-around porch with multiple seating areas. Large windows allow for ample natural light, while the light-colored exterior complements the serene surroundings. The property is partially surrounded by trees, enhancing privacy.

Home in Machipongo

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

FamilyValueDecor

4.99 out of 5 average rating, 136 reviews

Top guest favourite

The red brick duplex features a welcoming front porch with white rocking chairs on both sides. Two main entrances are visible, framed by classic black shutters, while the well-maintained yard is accented with small plants. The evening sky casts a gentle light over the structure.

Home in Cape Charles

Stylishly Renovated | Golf Cart Avail. | Bakery!

Nectarine 15 is centrally located. Next door, you’ll find the Coastal Bakery. A great place for breakfast or Treat. Relax on the charming front porch and soak in the calm, historic vibe of Cape Charles. A Quick walk to historic Downtown, Take a swim in the bay or cast a line off the dock. Central Park is also nearby, offering a great spot for a family picnic while the kids enjoy the playground. Golf carts are available to rent(Cart Rentals are only available during the House rental period)

FamilyLocationDecor

4.94 out of 5 average rating, 195 reviews

Guest favourite

A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.

Cabin in Cape Charles

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, feed the Alpacas, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

ValueFamilySleep quality

4.96 out of 5 average rating, 268 reviews

Top guest favourite

The exterior of a red barn is shown, surrounded by lush green fields. The structure features a peaked roof with a cupola, multiple windows, and an inviting porch area with wooden steps. The surrounding farmland creates a serene atmosphere.

Barn in Cape Charles

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.

ValueLocationParks

5.0 out of 5 average rating, 101 reviews

Top guest favourite

A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.

Tiny home in Cape Charles

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.

LocationFamilyCleanliness

4.98 out of 5 average rating, 363 reviews

Top guest favourite

The duplex features a light blue exterior with a welcoming front porch. Rocking chairs are arranged alongside the entrance, inviting relaxation. The well-maintained lawn is complemented by tidy landscaping and a concrete pathway leading to the front steps.

Home in Cape Charles

Steps to the Sea at Salt Box

Escape to The Salt Box, a charming 1915 duplex just one block from the beach in the heart of Cape Charles' Historic District. This cozy, private retreat sits on a peaceful, tree-lined street and is a short stroll to the beach, pier, shops, restaurants, and more! Check out our local Guidebooks or text us anytime—we're happy to share our favorite local spots! Looking for even more space? You can also book the other half of our duplex, Salt Box II!

FamilyLocationCleanliness

4.97 out of 5 average rating, 315 reviews

Top guest favourite

The front porch features two bright yellow doors welcoming guests, flanked by white railings and steps leading up to the entry. Potted plants and green grass enhance the outdoor space, while a large tree provides shade in this inviting setting.

Home in Cape Charles

The BeeHouse

Breathe in the Beehouse! Newly built, this well equipped modern house features high ceilings with a clean crisp design with bright tropical colors and natural touches that truly transport you! Treat yourself to the tranquil Cape Charles lifestyle where you won’t see a clock because the local church chimes on the hour. Huge outdoor living space embraces you and allows you to take it all in. Have the sweetest vacation at the Beehouse!

FamilyLocationHeating

5.0 out of 5 average rating, 109 reviews