Vacation rentals in Cheriton

Farm stay in Cape Charles

5 out of 5 average rating, 383 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, 244 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.

4.97 out of 5 average rating, 116 reviews

Wander Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

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!

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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!

4.96 out of 5 average rating, 165 reviews

Tiny home in Diggs

Stargazer Tiny Cabin

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.

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Other great vacation rentals in Cheriton

4.5 out of 5 average rating, 34 reviews

1903 By the Sea - Minutes from Cape Charles

TanyaRating, 5 stars11 months ago

Lovely home with big and spacious bedrooms. Short drive to Cape Charles downtown area and beaches. Great home for large families. My family had a great time.

4.6 out of 5 average rating, 10 reviews

Cherrystone Charm

KathleenRating, 5 stars10 months ago

Our family had a great time at Catherine's place. It's a quick 5-7 minute drive to historic Cape Charles with shops and dining and also the beach. The house had a cute, beachy decor with little areas like the game room and the back sun porch where our family could spread out when needed. The kitchen had everything we needed ...there is great local seafood nearby so we did a big dinner one night. Besides going into Cape Charles, we enjoyed a morning at Kiptopeke State park which is about 10 minutes away. They have bikes and kayaks to rent as well as a nice beach area. This house was perfect for exploring the Eastern Shore of Va!

5 out of 5 average rating, 10 reviews

Condo in Cape Charles

The Port - Large condo on Mason Avenue!

DawnRating, 5 stars3 weeks ago

This is truly a hidden gem in Cape Charles! We recently stayed for the long holiday weekend and loved every minute of our trip. The apartment is absolutely beautiful and the location couldn't be better. We enjoyed having the ability to walk around town and have stores and restaurants so close by. The host was friendly and helpful and quick to respond to any questions we had. We look forward to staying here again!

4.73 out of 5 average rating, 15 reviews

Charming Cape Charles Vacation Rental Home!

RobbieRating, 5 stars10 months ago

We had two cars arriving at two different times with some crazy storms and yet the check-in was a breeze. We had long beach days and then came back to cook hearty meals in a clean and equipped kitchen, chef's dream. We also loved sitting around the kitchen table playing games from their collection. The rooms upstairs had super comfy beds with fresh linens. All bathrooms were full bathrooms which really helped accommodate all of us. They were we also pristine and clean. Even though we spent most of the sun-time at the beach and rain-time at the home, the backyard was large and lush. It would be perfect space to escape and read a book or go play tag. It was a perfect spot for a family to gather to reconnect and relax. I would definitely return for a future getaway.

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.

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!

4.95 out of 5 average rating, 91 reviews

The Shore House on Madison - Pet Friendly Unit!

CarolineRating, 5 stars2 weeks ago

Rachel’s place was wonderful. She provided clear instructions and the house was so clean and welcoming. Only complaint is her bathrooms only had 3-in-1 shampoo, conditioner, and body wash - if you plan on staying I’d advise to bring your own toiletries. Other than that everything was wonderful!