Holiday rentals in Smith Beach

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!

4.98 out of 5 average rating, 226 reviews

Flat in North

Little Cove Cottage, Couples Retreat/Mathews

Little Cove Cottage: a charming studio in Mathews County with private entrance. Mathews is a rural town with several beautiful beaches close by and many areas to access the water. This apartment offers a small water view of the North River, with a pier and boat ramp just 400 yards away. Bring your Kayaks or use ours. . We are just minutes away from the Mobjack and Chesapeake Bays. Mathews is home to great restaurants with fresh seafood. We also have a wonderful farmer's market. Come enjoy!

Townhouse in Cape Charles

4.95 out of 5 average rating, 145 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, 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, 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.

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 Smith Beach

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!

Home in Gloucester County

4.95 out of 5 average rating, 56 reviews

York River | Chesapeake Bay Bliss: Fishing Retreat

MagdaRating, 5 stars2 months ago

Our family of four loved staying here. Our 10-year-old delighted in crabbing and playing board games (chess and Battleship). Our 7-year-old desperately wanted to splash around the York River even though it was freezing in April. The local recommendations were much appreciated and the impact of staring at a horizon line cannot be overestimated.

5 out of 5 average rating, 80 reviews

Home in Machipongo

Private Country Beach Retreat

RuthRating, 5 stars4 days ago

Kristy’s place was so peaceful! If you are looking for a quiet space then this is the place for you! Everything from the location to the details in the home curated a calm environment. And if you need to hear a little noise Cape Charles is just a drive away! Also check out the lovely Chatham vineyard just down the road!

Superhost

4.9 out of 5 average rating, 31 reviews

Cape Cottage B (Upstairs)

ShannonRating, 5 stars5 days ago

Quiet and beautiful place with some great walkable restaurants and bakeries. The bed and place was so comfy!

Cottage in Gwynn's Island

4.92 out of 5 average rating, 36 reviews

Little Gray Beach House

MattRating, 5 stars1 day ago

Great getaway place, super peaceful, and quiet. Beautiful views. Just a few helpful tips for your visit …might want to bring tin foil, plastic wrap, etc. We didn’t care for the taste of the tapwater, may want to bring your own. Matches for the grill were found in the utility room. Shed had plenty of extra space to store our 2 bikes, could fit 3-4. Highly recommend, we would definitely stay here again!!

5 out of 5 average rating, 21 reviews

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

HillaryRating, 5 stars5 days ago

We had a great time in Cape Charles! The house was nice, clear, and was ready early for us to check-in. It was also a nice surprise to see the local coffee, treats, and coupons to help is enjoy our stay and explore the town. The house is right next to the park, and walkable to the beach but we rented a golf-cart for the week. There was plenty of street parking between neighbor cars and carts. Chip was super responsive and practice throughout the trip, clearly trying to make vacation as smooth as possible. Overall a great host and experience.

Superhost

Home in Hudgins

4.83 out of 5 average rating, 6 reviews

Chesapeake Bayfront Home with Amazing Views!

KezeRating, 5 stars4 weeks ago

Definitely will be going back! Liked it so much I didn’t want to go home lol. Probably rent again in June. Only thing I recommend them to do is to update the pier it is useable. Just use extreme caution! Otherwise absolutely outstanding place!