Holiday houses in Oyster

Farm stay in Cape Charles

5 out of 5 average rating, 384 reviews

Private Guesthouse on Secluded Waterfront Farm

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.

4.93 out of 5 average rating, 245 reviews

Loft in Cape Charles

The Cheriton Loft

Located in the heart of Cheriton, The Loft is a bright and sunny apartment. It is perfect for a couple and one child, three friends or one person. Cheriton is an up and coming village which is home to several galleries and an art center. It is less than 4 miles to the charming town and beach of Cape Charles, 3 miles to Oyster Boat Landing and 8 miles to Kiptopeke State Park. The apartment is owned and decorated by"The Sheep Lady", a local painter, illustrator and writer of children's books.

4.99 out of 5 average rating, 265 reviews

Farm stay in Onancock

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!

Tiny home in Cape Charles

4.89 out of 5 average rating, 125 reviews

Summer Camp Tiny Cottage Walk to the beach & shops

LAST OPEN SUMMER DATES: 7/30, 8/3-10 + 8/14-22 At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below!

Tiny home in Cape Charles

4.98 out of 5 average rating, 317 reviews

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.

4.89 out of 5 average rating, 101 reviews

"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!

4.96 out of 5 average rating, 176 reviews

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, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

4.96 out of 5 average rating, 253 reviews

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!

Superhost

Cottage in Cape Charles

4.78 out of 5 average rating, 113 reviews

Sea Salt Cottage: Tranquil Getaway 5 min to beach

Escape to the Eastern shore! Sea Salt Cottage is your quiet, off-the-beaten path getaway in charming Cape Charles. -Peaceful, rural feel with a 5 min drive to beach, quaint shops & restaurants. -Dog & kid friendly w/ large yard to park boats, RV's, etc. -Hammock, tree swing, outdoor dining, fire pit, romantic sunsets. -2 min to groceries, 10 min to Kiptopeake State Park, 70 min to Chincoteague Island

Townhouse in Cape Charles

4.93 out of 5 average rating, 145 reviews

Cozy retreat 2Bedroom/2Bath, 3 Blocks to Beach

Welcome to Peach Haven II! Renovated in 2021, this pet-friendly duplex in Cape Charles’ historic district sleeps 5. One block from a park with playground and tennis/pickleball courts, and 3 blocks from the beach. Features 1 bedroom (queen bed) and a 2nd with a custom full-size bunkbed. Stocked for comfort. Ask about renting the other side for more space!

Guest suite in Machipongo

5 out of 5 average rating, 107 reviews

Peaceful Suite in Machipongo

Welcome to our soul-nourishing space perfect for your getaway! A magical place where time seems to stand still in the peace and tranquility. Nature beckons as birds fly back and forth, chimes sing in the breeze, stars glisten in the sky. Welcome to Feather Tree Retreat, a refreshing haven on the Eastern Shore of Virginia!

4.98 out of 5 average rating, 314 reviews

Tiny home in Machipongo

Machipongo Glamper

Close your eyes. Imagine a salty breeze and a view of a vineyard from your spot tucked into the back of our rural 5 acre spot. The stars are brighter, the clams are saltier, and the pace is slower. At night, the stars go on forever and in morning a perfect view of the sun rising over the neighbor’s field.

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Other great holiday rentals in Oyster

Farm stay in Cape Charles

4.95 out of 5 average rating, 19 reviews

Scott Farms Cottage

LisaRating, 5 stars7 months ago

I recently had the pleasure of staying at a charming Airbnb in Brittany, and I can't recommend it highly enough! From the moment I arrived, I was greeted with warm hospitality and a cozy atmosphere that made me feel right at home. The location was perfect, nestled between picturesque landscapes and charming coastal towns. The host was incredibly attentive, providing helpful tips on local attractions and restaurants that truly enhanced my experience. The accommodations were spotless, beautifully decorated, and equipped with all the amenities I needed for a comfortable stay. One of the highlights was enjoying my morning coffee on the terrace, taking in the stunning views of the surrounding countryside. The peaceful ambiance made it a perfect escape from the hustle and bustle of everyday life. Overall, my stay in Brittany was unforgettable, and I would wholeheartedly recommend this Airbnb to

Tiny home in Cape Charles

4.9 out of 5 average rating, 179 reviews

Unique, luxurious creekside stay in Cape Charles

ChristyRating, 5 stars1 month ago

We loved the location and the home! It was quite lovely!

4.9 out of 5 average rating, 10 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

ThomasRating, 5 stars2 weeks ago

Nate was very responsive from booking , all the way through our stay. He was very flexible due to our circumstances and juggling vacation with 2 young children and 2 labradors. I would recommend this home to anyone with a family or pets as it offers the interior space that cape Charles historic homes lack while maintaining the same proximity to the town’s attractions.

4.93 out of 5 average rating, 27 reviews

Cottage in Cape Charles

The Crew's Quarters: Steps from the Bay

SueRating, 5 stars2 weeks ago

Caryn’s home was perfect for our needs. She was very responsive to our question and provided valuable information about the area.

Superhost

Bungalow in Cape Charles

5 out of 5 average rating, 11 reviews

"Bungalow Bay"

TaylorRating, 5 stars3 weeks ago

Had a wonderful anniversary stay here with my husband and we would definitely stay here again! The house was very clean which we appreciate greatly and everything was just as we needed it.

5 out of 5 average rating, 7 reviews

Historic Shore Home w Boat Parking, Pet Friendly

KristinRating, 5 stars2 weeks ago

We greatly enjoyed our short break at Kristin's lovely home! The beds were very comfortable, the kitchen had everything we needed, the house was spotless. My favorite spot is the front porch for morning coffee. It's a very charming home with lots of character. And it's in a quiet location, yet still near the water and town. We also appreciated being able to bring our two pups, who loved the long nature trail at Oyster. We bought clams from nearby Cherrystone Aqua Farms - fantastic! El Ranchito has great Mexican food and the Cape Charles Coffee House is always worth a visit for breakfast. All in all, a great place to relax and recharge - a little slice of heaven!