Vacation rentals in Smith Beach

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, 243 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, 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!

4.97 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, 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, 175 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, 122 reviews

Home in Gloucester Point

Charming coastal home w/ outdoor area and river views

Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the historic triangle, or just take it easy around the house and enjoy the outdoor area, the choice is yours.

4.94 out of 5 average rating, 524 reviews

Guesthouse in Saluda

Wooded Cabin retreat on fresh water pond

If your looking for a quiet place in a wooded setting, this is it. Cabin has view of private 7.5 acre pond, deck and walking trail to the scenic Dragon Run, with canoe portage. You are welcome to bring your canoe/kayak. Bird watchers, wildflower enthusiasts will enjoy what the Dragon Run has to offer. If shopping or history is your interest, this cabin is only 45 min away from Williamsburg, and will give you a place to relax. This is a pet friendly cabin.

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!

4.97 out of 5 average rating, 281 reviews

Guesthouse in Yorktown

Charming Yorktown Battlefield Cottage

Kick back and relax after a day of touring the historic triangle. This space was originally built as an artists studio for renowned folk artist Nancy Thomas. The amount of natural light is wonderful and there are still some paint remnants from its former days as an artists studio adding to its unique character and history.

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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Popular amenities for Smith Beach vacation rentals

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Other great vacation rentals in Smith Beach

4.99 out of 5 average rating, 72 reviews

Cottage in Cape Charles

The Ladybug - arcade, dog-friendly, firepit, & EV

SandraRating, 5 stars2 weeks ago

Fabulous stay at the Ladybug! Host was outstanding with communication and responsiveness. House was exactly as described if not better. Location was not far from places to go yet so secluded and peaceful. Wish we could have had more time there and looking forward to coming back soon. Thank you!!

4.92 out of 5 average rating, 36 reviews

Home in Port Haywood

Anne's Beachfront Shangri-La

VickiRating, 5 stars4 days 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!

4.97 out of 5 average rating, 77 reviews

Treehouse in Machipongo

The Waverly Treehouse

GeorgeRating, 5 stars2 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!!! ⭐️ ⭐️⭐️⭐️⭐️

4.84 out of 5 average rating, 79 reviews

Home in Machipongo

The Farmhouse at Chatham Vineyards

DawnRating, 5 stars1 day ago

We had the best time at the farmhouse! The house is as described. Definitely a wonderful opportunity to unplug. The bedding was amazing and Eleanor and her husband were quick to respond with a downstairs AC unit which was a game changer! We loved our flight tasting at the winery and bought a bottle to take home. Great porch sitting time. Read the story of the farm - so interesting. Thanks for your hospitality!

5 out of 5 average rating, 20 reviews

Renovated by Central Park-Walk 2 Beach! King Bed!

KaraRating, 5 stars3 weeks ago

Very clean and nice space right near town and beach. Modern design and amenities like coffee, upscale soaps, charging ports on nightstands, and large TVs were a nice surprise. They also had a wagon, beach chairs, and beach umbrella that you can use. It was also nice to have a dishwasher and washer and dryer available. Location felt very safe and literally a few minute walk to town and beach! Would recommend.

Cottage in Gwynn's Island

4.91 out of 5 average rating, 34 reviews

Little Gray Beach House

CorrineRating, 5 stars1 week ago

We loved our short stay at the Little Gray House. The view alone was worth the stay. The beaches are both easy walks and the area is lovely. Everything was clean and cozy and Bronwyn and Kat gave lots of information ahead of time, including some great recommendations. Would definitely recommend checking out The Hatchery and the Gwynn’s Island Museum on the island and spending some time exploring Mathews. We will be staying here again and hopefully soon!