Holiday rentals in Cape Charles

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.

Guest house in White Stone

5 out of 5 average rating, 245 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.

4.94 out of 5 average rating, 121 reviews

Cottage in Hacksneck

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

4.99 out of 5 average rating, 263 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!

4.93 out of 5 average rating, 124 reviews

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)

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.

4.96 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.

4.95 out of 5 average rating, 108 reviews

Sunshine Rays: Historic district backyard bliss!

Situated on a peaceful block of Cape Charles' charming historic district, Sunshine Rays was designed as a retreat for families visiting the Eastern Shore. With space for up to eight guests, an incredible backyard, and thoughtful amenities throughout, it's the perfect base for your Cape Charles getaway. We are just six blocks from the beach and even closer to our Central Park and the town's main street with all of its restaurants, bakeries, and shops.

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!

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Popular amenities for Cape Charles holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Cape Charles

5 out of 5 average rating, 45 reviews

Barn in Cape Charles

Coastal Red Barn Retreat

StephanieRating, 5 stars3 weeks ago

The Barn is a beautiful place to stay. The craftsmanship is impressive. The home was immaculate, and the neighborhood is peaceful. The starter kit made travel so much easier, since we didn’t have to worry about bedding, paper products, etc. The welcome book sent ahead of time was perfect to start thinking about how we would spend our time. It’s in a great location. Close to the beach, downtown, hiking, shopping, and dining. Then to come home to relax in the jacuzzi, by the fire pit, watch the sunset over the fields, or play games. Our family had a great vacation thanks to how comfortable Hunter and family made everything.

4.92 out of 5 average rating, 36 reviews

Home in Port Haywood

Anne's Beachfront Shangri-La

VickiRating, 5 stars1 week ago

We had a wonderful stay at Brandon’s place! It was private and beautiful! The house also contained everything we could possibly need from kayaks to a pack and play! We will definitely be back! Thank you!

4.94 out of 5 average rating, 81 reviews

Celebrating 100 years!

KaceyRating, 5 stars4 days ago

Absolutely perfect vacation spot for a coastal getaway! We brought our dog and had a blast walking around town, to the beach, and enjoying the beautiful weather of Cape Charles. The neighborhood was quiet and in walking distance to everything in the historic downtown. The park across the street was beautiful and our pup enjoyed sniffing around! We will definitely be back.

4.9 out of 5 average rating, 10 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

ThomasRating, 5 stars1 week 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.

4.97 out of 5 average rating, 77 reviews

Treehouse in Machipongo

The Waverly Treehouse

GeorgeRating, 5 stars3 weeks ago

We had a delightful stay in the Waverly treehouse. We definitely recommend checking it out. The amenities and host were absolutely wonderful and the trip exceeded all of our expectations. Thank you!!! ⭐️ ⭐️⭐️⭐️⭐️

5 out of 5 average rating, 8 reviews

Flat in Cape Charles

Romantic Coastal Retreat w/ Private Balcony

ArdynRating, 5 stars3 weeks ago

Charming getaway in the heart of Cape Charles! Juliet was full of charm and meticulously clean and we absolutely loved our stay! Thank you Clelia!!

Superhost

4.67 out of 5 average rating, 6 reviews

Lil Ms. Clementine-Historic District Golfcart opt.

MorganneRating, 5 stars2 weeks ago

Cheri’s house was perfect for our family’s annual long weekend in Cape Charles! Everything was easy to find with her clear instructions, the house was cozy and had all the amenities one could need, and we actually liked staying a little farther from the action. Everything is a short golf cart ride away and the street was quiet and friendly. The game closet was such a sweet bonus! My kids got up at 6 on their first day of summer break—go figure—and it was lovely to have some new games to play until everything opened. We already booked for next year!