Holiday houses in Silver 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.

4.95 out of 5 average rating, 237 reviews

Cottage in Onancock

Eastern Shore Romantic Waterfront Getaway Upscale

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles >save listing to your wishlist<<

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.

Guesthouse 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, 122 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, 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!

4.96 out of 5 average rating, 110 reviews

Home in Belle Haven

Bay Breeze Home on private waterfront

On Virginia's beautiful Eastern Shore, the Bay Breeze Home on Occohannock Creek is the ultimate getaway for two or a large family desiring outside adventures. This 1970's spacious home has plenty of room. Experience the water with our three kayaks or family canoe and watch the abundant wildlife. Right outside your door, you may see Ospreys, Great Blue Herons, Eagles, wild ducks, porpoises, deer, geese, otters, & more. Be our guest and forget your worries in this spacious and serene spot.

4.97 out of 5 average rating, 116 reviews

Home in Cape Charles

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.

4.96 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.

4.89 out of 5 average rating, 353 reviews

Cottage in White Stone

The Moore Cottage

The Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

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 Silver Beach

4.8 out of 5 average rating, 143 reviews

Home in Nassawadox

Brownsville Cottage

LindseyRating, 5 stars2 months ago

The house is in a quiet neighborhood and very little noise was heard when you’re inside. The house is older and does need some maintenance but nothing that hindered us from having a nice stay! Also, added bonus - no checkout cleaning requirements!

Guest suite in Cape Charles

4.98 out of 5 average rating, 51 reviews

Chesapeake Retreat - Bay view

CathleenRating, 5 stars1 week ago

Comfortable, clean, and spacious unit. I stayed here for a wedding at the Mimosa Barn which was a 4 minute drive. Cape Charles and other activities were a 10 minute drive. Margaret provided snacks, coffee & creamer, and a bottle of prosecco for us to enjoy. The neighbor's dogs greeted us when we checked in - they are very friendly but be aware they may run in front of your car when pulling in so watch out (especially at night!). There is a private entrance. The unit is connected to the rest of the house by a set of stairs which were blocked off by a styrofoam wall and a curtain. It felt very private - we did not see the host, or even any neighbors during our stay.

4.89 out of 5 average rating, 94 reviews

Cottage in Painter

Cottage by the bay (private peaceful surroundings)

JamesRating, 5 stars1 week ago

It was a pleasure finding this peaceful home. It is nestled in a rural area of Maryland. If you need to get away from life for a reset, this is the perfect place. The host was extremely responsive and flexible. The home is nicely accommodating and the local area has a nice park and dock to enjoy the water. I would highly recommend staying. James P

4.76 out of 5 average rating, 17 reviews

Home in Belle Haven

Huge Waterfront Patio-Private Dock! King Size Beds

susanRating, 5 stars4 days ago

Unbelievable views. Very comfortable! Safe area.

4.94 out of 5 average rating, 50 reviews

Cabin in Onancock

Awesome private off grid cabin with creek view.

DanielRating, 5 stars3 weeks ago

This place was as described. Very peaceful get away for my family and totally worth the price we paid. Teresa was quick to respond and recommended some place to eat. We will be back to experience the fall weather.

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!!

4.84 out of 5 average rating, 79 reviews

Home in Machipongo

The Farmhouse at Chatham Vineyards

DawnRating, 5 stars6 days 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!