Holiday rentals in Cheriton

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.

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, 8/3-7 (Sun-thurs) + 8/17-22 (Sun-Fri) 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!

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.

Guest house in White Stone

5 out of 5 average rating, 246 reviews

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.

Townhouse in Cape Charles

4.95 out of 5 average rating, 146 reviews

3 Blocks to Beach, Fenced Backyard, Pet Friendly!

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!

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

4.98 out of 5 average rating, 318 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, 177 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

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!

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Other great holiday 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.

Superhost

4.95 out of 5 average rating, 42 reviews

Hot Tub/Fire Pit/Yard Games! Lots of space!

AmyRating, 5 stars2 weeks ago

Beautiful home in Cherrystone, just 10 min drive to Cape Charles. Very convenient with all the perks of a well stocked kitchen, hot tub, & yard games. The home was large enough for our 8 guest, offering several spaces to relax. Our favorite spot was the kitchen table & outdoor spaces! The home was very clean, offered beach towels & all basic household supplies. We will definitely be back!

Tiny home in Cape Charles

4.88 out of 5 average rating, 181 reviews

Unique, luxurious creekside stay in Cape Charles

ChristopherRating, 5 stars2 weeks ago

The tiny home was a perfect fit for our vacation. It is a great place for a couple to stay on a vacation. It is reasonably close to downtown Cape Charles and Virginia Beach, with beach access a short walk away. It is a good fit for whatever beach type vacation you're looking for.

4.73 out of 5 average rating, 15 reviews

Charming Cape Charles Vacation Rental Home!

RobbieRating, 5 stars11 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.

4.9 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 stars3 weeks ago

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