Vacation rentals in Machipongo

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Top-rated vacation rentals in Machipongo

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Guest favorite

Tiny home in Cape Charles

4.94 out of 5 average rating, 146 reviews

Unique, luxurious creekside stay in Cape Charles

Newly remodeled and ready for your next getaway! This tiny home is located just steps away from a calm, private beach. The interior decor creates a modern coastal feel to fit the style of the home. Creek views can be enjoyed from every window of the home and from the loft bed. It features a full kitchen with quartz counter tops, a fully tiled bath, outdoor shower, grill, large front porch and a nice sized back yard with added privacy fencing. Enjoy our fire pit with twinkle lights strung above.

Oct 19 – 26

$180 per night

Guest favorite

Tiny home in Accomac

4.93 out of 5 average rating, 439 reviews

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a tiny house with big charm. This rural cottage on a 50 acre farm is nestled between peaceful fields, woods, marsh and creek. Curated with hygge comfort and efficiency in mind, you'll love the natural light and serene decor. • Epic stargazing • Heavenly private outdoor shower • Firepit with wood provided • Ample open spaces • Peace and quiet for sleeping • Comfy patio seating for chilling, coffee, and cocktails • Fast Starlink WIFI. • Proud Superhost for 10+ years!

Sep 16 – 23

$104 per night

Guest favorite

Loft in Cape Charles

4.92 out of 5 average rating, 204 reviews

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.

Sep 21 – 28

$78 per night

Guest favorite

Bungalow in Belle Haven

4.92 out of 5 average rating, 178 reviews

Stay Waterfront-Private Dock Belle Haven Bungalow

Come explore the Eastern Shore - Waterfront bungalow with fishing / crabbing pier. Our two bedroom, two bath bungalow sleeps up to 7 guests comfortably. Open floor plan and large screened porch / deck make our modest bungalow feel like a much bigger place. Perfect setting for a family vacation you will never forget. Kayaks, Fishing / crabbing gear and yard games are all available for use during your stay. 35 minute drive to Cape Charles beach and many other adventures in every direction.

Sep 28 – Oct 5

$165 per night

Guest favorite

Farm stay in Onancock

4.99 out of 5 average rating, 172 reviews

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!

Feb 11 – 18

$156 per night

Guest favorite

Farm stay in Cape Charles

5.0 out of 5 average rating, 330 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 urban centers. Our twenty acre waterfront farm, which has plenty of nearby walking or biking, and a dock onto a secluded arm of Plantation Creek, an inlet of the Chesapeake Bay, is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Aug 26 – Sep 2

$164 per night

Guest favorite

Home in Cape Charles

4.99 out of 5 average rating, 104 reviews

Modern Private Beach House close to 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.

Oct 18 – 25

$723 per night

Guest favorite

Farm stay in Cape Charles

4.96 out of 5 average rating, 158 reviews

Airstream Retreat Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning Airstream retreat 10 mins from Cape Charles. The 1969 Airstream has been converted into a contemporary studio with all the comforts of a luxury hotel room. Wake up to the birds singing in the trees that completely surround the huge front deck. Take a walk on our trails. Enjoy watching the animals. Take a trip into Cape Charles for restaurants and shopping, then enjoy a movie in the Airstream at night.

Oct 9 – 16

$171 per night

Guest favorite

Cottage in Gloucester

4.97 out of 5 average rating, 193 reviews

"Bee Haven" Cottage Retreat

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Haven Retreat" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Jan 6 – 13

$103 per night

Guest favorite

Tiny home in Cape Charles

4.98 out of 5 average rating, 271 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.

Mar 11 – 18

$225 per night

Guest favorite

Cottage in Onancock

4.97 out of 5 average rating, 194 reviews

Waterfront romantic getaway Eastern Shore w dock

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

Dec 7 – 14

$157 per night

Guest favorite

Cottage in White Stone

4.91 out of 5 average rating, 297 reviews

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!

Jul 31 – Aug 7

$105 per night