Holiday houses in Nassawadox

4.94 out of 5 average rating, 488 reviews

Tiny home in Accomac

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a cozy tiny home on a 50-acre farm, surrounded by fields, woods, marsh, and a creek. Curated with hygge comfort and efficiency, you'll love the natural light and calm decor. • Escape the noise & reset in nature • Peaceful sleeping • Thoughtful interior design • Large full bath • Comfy patio for coffee, cocktails, and epic stargazing • Firepit with wood provided • Large private outdoor shower surrounded by woods • Wide open spaces • Fast WIFI • Superhost for 10+ years

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, 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.

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.

4.98 out of 5 average rating, 267 reviews

Home in Accomac

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

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.

4.75 out of 5 average rating, 211 reviews

Guest suite in Crisfield

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

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 Nassawadox

4.7 out of 5 average rating, 10 reviews

Home in Exmore

Striped Bass Inn

JohnRating, 5 stars9 months ago

Great place to stay in exmore

Guest suite in Cape Charles

4.98 out of 5 average rating, 50 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

5 out of 5 average rating, 79 reviews

Home in Machipongo

Private Country Beach Retreat

AaronRating, 5 stars2 weeks ago

Absolutely amazing stay. The house is beautiful and the location could not be better. The biggest regret I have is not staying longer. If you are thinking about booking, do yourself a favor and do it now!

5 out of 5 average rating, 15 reviews

Cottage in Exmore

ESVA Silver Beach Getaway August week open

WendyRating, 5 stars1 month ago

Such a cute, well stocked and clean cottage. Extremely quiet neighborhood. Sunsets over the bay were stunning. Jennifer was easy to teach and communicate with.

4.76 out of 5 average rating, 17 reviews

Home in Belle Haven

Huge Waterfront Patio-Private Dock! King Size Beds

susanRating, 5 stars3 days ago

Unbelievable views. Very comfortable! Safe area.

4.84 out of 5 average rating, 79 reviews

Home in Machipongo

The Farmhouse at Chatham Vineyards

DawnRating, 5 stars5 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!