Vacation rentals in Craddockville

4.94 out of 5 average rating, 490 reviews

A ceramic vase filled with a bouquet of fresh flowers is placed on a wooden countertop. The arrangement includes white magnolia blossoms, yellow coneflowers, and small orange flowers, providing a natural touch to the bathroom's decor.

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

4.78 out of 5 average rating, 18 reviews

A plate of freshly shucked oysters lies on a ledge, accompanied by two glasses of golden beer. The serene waterfront scene is visible in the background, showcasing a wooden dock surrounded by calm water.

Home in Belle Haven

Huge Waterfront Patio-Private Dock! King Size Beds

Stunning views. Authentic ESVA waterfront experience. Newly renovated & furnished June ‘24. One of a kind, custom designed home, inspired by Frank Lloyd Wright. New accessible spa bath/ en suite. Fully equipped kitchen. MCM style with comfort in mind. Private and peaceful. Convenient & easy to explore the Shore. Fish, crab, kayak, birdwatch. Play piano, games. Our guests love being here- and our family does, too. Set up with plenty of space for family and friends to gather, relax, & have fun!

4.8 out of 5 average rating, 145 reviews

A spacious dining area features a wooden table with attached benches, positioned near a brick fireplace. Adjacent seating areas are visible through large, panoramic windows, allowing views of the outside greenery and water, enhancing the inviting atmosphere of the cottage.

Home in Onancock

Charming Waterfront Cottage on Cedar Creek

Come unwind in this comfy cottage right on the water. Situated on a 2 acre wooded lot, this colonial home offers peaceful seclusion and unbelievable water views from every room. This 1930’s cottage has modern updates and plenty of room, with two large bedrooms downstairs and a delightful bedroom suite upstairs. Restaurants and shopping await in the historic town of Onancock, only a 5-minute drive or an even quicker boat ride away. Private dock for swimming and fishing, two kayaks for guest use.

4.95 out of 5 average rating, 238 reviews

Two white adirondack chairs are positioned on a wooden dock, facing a calm waterway. Soft pastel colors in the sky reflect on the water, creating a serene atmosphere. The surrounding landscape features trees and distant hills, enhancing the peaceful waterfront view.

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<<

4.98 out of 5 average rating, 132 reviews

A rustic sign displaying the text 'Welcome to BELL Farm Cottage!' is mounted on a wall. The sign features a weathered frame with a chalkboard surface, presenting a warm greeting to guests upon entry.

Cottage in Greenbush

Bell Farm Cottage LLC - quiet and peaceful

Cozy cottage located on a quiet backroad overlooking a wide open field & back deck provides warm & sunny space for relaxing or reading a book. The kitchen is fully equipped. BFC has a warm farm house feel w/ a touch of the beach. The bathroom has been updated to a more modern feel. Located only a few miles from both seaside and bayside boat ramps. A 7 minute drive to Onancock, Walmart, YMCA, shopping & many local shops for just the right souvenir. Wallops & Chincoteague are just a short drive.

4.94 out of 5 average rating, 122 reviews

An aerial view captures a secluded Victorian cottage nestled on a private island, surrounded by water and lush greenery. A footbridge connects the island to a winding path, merging into open fields and offering glimpses of the bay and forested areas in the distance.

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, 267 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!

4.9 out of 5 average rating, 96 reviews

A map illustrates six locations along the Virginia peninsula for viewing a Wallops flight launch. Notable sites include Wallops Visitor Center and Chincoteague Island, with the Wallops launch range clearly marked. Distances from Wallops and suggested activities are indicated for potential visitors.

Cottage in Painter

Cottage by the bay (private peaceful surroundings)

Privacy, peace, relaxation, togetherness … this cottage is the perfect place for memory-making with your family and friends! The kitchen is stocked with every spice and tool you may require to create a delicious meal, which can be enjoyed at the breakfast bar, large dining table, or outside, surrounded by the tranquil Virginia ambience. The shed, equipped with kayaks, paddle board, crabbing gear, bicycles, beach stuff chairs, has all you may need for a day on the bay or at the ocean.

4.96 out of 5 average rating, 112 reviews

Four black Adirondack chairs are positioned in a grassy area facing a tranquil body of water. Lush green reeds frame the water's edge, with a blue sky and scattered clouds above. A small dock is visible in the distance, adding to the serene setting.

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

A spacious great room features wooden beams overhead and a modern stone fireplace at one end. Cozy seating is arranged around a central coffee table, with natural elements incorporated into the decor. Artwork is displayed on the walls, complementing the warm, inviting atmosphere.

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.

4.92 out of 5 average rating, 237 reviews

A white stairway leads to the entrance of the guest house, surrounded by trees and natural landscaping. The calm waters of Onancock Creek are visible in the background, with a glimpse of moored boats and the shoreline beyond.

Guesthouse in Onancock

NEWLY Renovated -- Waterfront Getaway

Renovation - Siding, windows, doors, landing/stairs, flooring, foam insulation, paint, min-split AC/heat unit. Nestled comfortably on an acre along Onancock Creek, this quiet one-room guest house boasts a full kitchen, Serta queen size bed, TV/internet, and incredible scenery of the creek. Spend a weekend exploring historic Onancock, with its unique shops and variety of cuisine, or rent kayaks in town for a relaxing cruise on the creek to watch the sunset over the Chesapeake Bay.

Tiny home in Cape Charles

An aerial view showcases the serene Chesapeake Bay, where sandy tidal flats create patterns in the water. The coastline blends with lush greenery in the background, while gentle waves reflect the clear blue sky.

4.98 out of 5 average rating, 318 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.

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Other great vacation rentals in Craddockville

5 out of 5 average rating, 11 reviews

Two red mugs are positioned on a wooden stump, with a s'more crafted from graham crackers, chocolate, and marshmallows placed in the center. Soft, warm light highlights the scene, creating a cozy atmosphere around the outdoor fire pit.

Camper/RV in Belle Haven

Belle Haven’s Bliss

MatthewRating, 5 stars3 days ago

Very friendly and responsive. I locked the keys in the camper and she was very responsive and that hiccup did not affect the plans for the evening. The space is very peaceful and quiet. You cannot see the road from the camper.

5 out of 5 average rating, 47 reviews

Home in Heathsville

Northern Neck Creek Retreat w/ king suite, firepit

JulietteRating, 5 stars1 month ago

Creek Retreat is a perfect place to kick back and relax. Surrounded by nature, a private oasis. The space is well appointed, clean and comfortable. Tastefully decorated. Added amenities and attention to details elevate the experience. Enjoy kayaking and sitting by the fire. Georgia is a great hostess and is proactive and responsive. If you're looking for a getaway, book it here!

Apartment in Wachapreague

A modern kitchen features white cabinetry and a granite countertop island with seating for one. Stainless steel appliances and a farmhouse-style light fixture provide functionality and style. The open layout creates a seamless connection to the living space, enhancing the overall flow of the apartment.

4.94 out of 5 average rating, 70 reviews

Apt in Wachapreague | Seaside Village | Guest Fav

KristyRating, 5 stars1 month ago

Excellent stay. Allen was a pleasure to work with. Always responsive and quick. The place was spotless and had what we needed. The general store front door is adorable. I needed to have a work meeting through zoom while I was there and the internet was strong in the cottage. The town has spotty service. Thank you Allen. We would stay here again.

Place to stay in Machipongo

A fog-covered wooden dock extends into calm waters, with pillars rising above the surface. The muted sunlight creates a soft reflection on the water, while the surrounding atmosphere conveys a serene, tranquil quality.

5 out of 5 average rating, 75 reviews

Smokehouse on the Chesapeake Bay

ElizabethRating, 5 stars1 week ago

From beginning to end this little piece of Heaven did not disappoint! This was the most amazing get away we could have asked for. Such wonderful hosts!!! We loved our stay and cannot wait to return in the future!!!

4.84 out of 5 average rating, 79 reviews

The foyer features a staircase with wooden railings and a landing area illuminated by natural light. A vintage wooden chair is positioned beside a large glass-paneled door that opens to the outside, with a decorative rug placed on the polished floor.

Home in Machipongo

The Farmhouse at Chatham Vineyards

DawnRating, 5 stars1 week 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!

4.83 out of 5 average rating, 6 reviews

A spacious wrap-around deck is depicted, offering stunning views of the waterfront. Comfortable lounge chairs and a small table are visible, positioned near the home's entrance, with trees framing the scene. The sunset casts a warm glow, enhancing the serene environment.

Home in Hudgins

Bayfront Escape | Private Dock, Large Deck & Views

KezeRating, 5 stars1 month 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!

4.85 out of 5 average rating, 20 reviews

Home in Onancock

Craftsman Bungalow c. 1925

MaryRating, 5 stars8 months ago

This is a beautiful historic home that is in a quiet neighborhood. It is close to the downtown area which has lovely shops and is close to local restaurants. The home was comfortable and very relaxing. We had a little trouble getting in the home when we arrived. The hosts were extremely quick to respond and help us out. We would definitely stay here again.