Holiday houses in Chincoteague

4.94 out of 5 average rating, 109 reviews

Dragonfli Bay House on Chincoteague Island

Relax in this calm, stylish space. This home has been lovingly refreshed by its current owners. Every detail has been considered. Inside you will find well appointed rooms designed for function and comfort. Outside, tranquility awaits you. Enjoy morning coffee overlooking the water, kayak on Oyster bay, end the day relaxing by the fire. Head to Assateague to swim, surf fish or hike to the famed lighthouse. Return with the day's catch to utilize the fish cleaning station and outdoor shower.

4.94 out of 5 average rating, 489 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

4.92 out of 5 average rating, 149 reviews

Adorable Beach Cottage Just Steps From Town & Bay

New to AirBNB! Welcome to Wiggle Bay, a darling 1955 2 BR cottage nestled in the heart of "one of the most beautiful, charming small towns in Virginia." -Enjoy a bay breeze on the screened front porch--heaven! --Stroll to local bookshop, coffee house, theatre, or Chincoteague Waterfront Park to feed the ducks--all just steps from your front door! -Situated on a quiet residential street -Just 4 blocks to Maddox Blvd (where all the action is) -2.3 mi to Assateague Seashore/Chincoteague Refuge

Superhost

Cottage in Chincoteague

4.83 out of 5 average rating, 101 reviews

"3 Sisters" Ivy's Cottage-Lovely downtown cottage

Just a few miles from the Chincoteague National Wildlife Refuge & Assateague Beach. Ivy's Cottage offers a great in-town location that's close to shops, restaurants, waterfront park, & public fishing pier. This beautifully renovated, this Chincoteague Island Cottage Features: Lovely eat in kitchen, fully equipped w/ all amenities. Cozy living room w/ full sleeper sofa & recliner. Queen bedroom w/ adjacent full bathroom. Large front porch perfect for outdoor dining & park style charcoal grill!

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!

4.97 out of 5 average rating, 166 reviews

Charming Island Home "Sandy Pines"

Come and enjoy a nice, relaxing vacation at this charming island home. "Sandy Pines" lies just a half a block from the water and a block and a half from the bridge to Assateague (where the beach is). The downstairs features a living room and dining room, 2 bedrooms (equipped with two twin beds each), a lovely kitchen, full bathroom and screened porch. On the second level you'll find the master bedroom with a private full bathroom, movie/game/yoga room, and a 2nd fully screened porch.

Superhost

Houseboat in Snow Hill

4.87 out of 5 average rating, 131 reviews

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

4.95 out of 5 average rating, 113 reviews

The Neigh-Neigh - Location! Location! Location!

Named in honor of the ponies that first put Chincoteague on the map, this charming newly renovated family getaway is walking/biking/and wheeling distance to shops, galleries, restaurants, waterfront park, library, beach, wild ponies, and movie theater. Come relax in a stunning, clean, 2 BR, 2 full BA plus oversized upstairs den with queen and twin beds and a futon bed that comfortably sleeps 8. The amenities and unique offers this place has, is not to be missed.

4.99 out of 5 average rating, 227 reviews

Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Apartment in Chincoteague

4.86 out of 5 average rating, 189 reviews

Sunset Haven Downtown

Broadband WIFI newly installed and dependable! This special place is located in the heart of historic downtown Chincoteague above a wine shop/jewelry boutique. Your backyard is a waterfront park with our famous Love Chairs! Watch the sunset from your waterfront window or deck. Walk to shopping, restaurants, and more! An apartment with old time charm and new polished adds to feel as modern as needed! Onsite Laundry- Linens provided

Guest suite in Chincoteague

4.98 out of 5 average rating, 288 reviews

Baywatch Upper-Waterfront & Roaming Ponies!

Discounted rates for weekly rentals Summer ‘25. Beautiful space in and out! Situated right on the bay with views of Assateague across the way, Chincoteague ponies are on premises. Coastal charm at its finest, there are 2 queen bedrooms and livingroom/breakfast room, all with a view. No full kitchen. Microwave, toaster, small fridge, stocked Keurig coffee and tea station and shared outdoor cooking area, sink and bbq grill.

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 Chincoteague

Superhost

Cottage in Chincoteague

4.72 out of 5 average rating, 100 reviews

SNUG HARBOR waterfront cottage with a grand view!

AlexandraRating, 5 stars2 weeks ago

We ABSOLUTELY loved our visit, and plan to return and stay with Basia! Our weekend consisted of rainy weather and she offered us a covered porch which was well worth it!! Each morning we had a peaceful water view with the horses in the distance. I don’t think it could get any better. The boat tour was SO much fun. Basia stayed in contact with us about when would be the better time to go. She really looked out for us when the weather would be at its peak. Her recommendations never failed to impress. Thank you SO much for having us!! We plan to be back.

5 out of 5 average rating, 10 reviews

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon

JillianRating, 5 stars6 days ago

Had a wonderful stay! The entire family enjoyed the little beach and dock. Our son caught us crabs to eat every day and our daughter was in the water constantly! Very peaceful sitting on the back deck.

4.97 out of 5 average rating, 69 reviews

Pelican Sunset - Waterfront With Pier

HollyRating, 5 stars8 months ago

We loved watching the sunset and the dolphins from the beautiful private dock. The deck upstairs was perfect for stargazing. The beds were comfortable and the house was adorable. Chincoteague is super cute with plenty of shopping, restaurants, and natural beauty.

4.98 out of 5 average rating, 49 reviews

cozy sunset cottage

ZaneRating, 5 stars5 days ago

the place was beautiful and felt very cozy! It was a very short drive to and from the beach as well with plenty of things to do nearby!

Townhouse in Chincoteague

5 out of 5 average rating, 4 reviews

Misty Mare Townhouse

LaurenRating, 5 stars2 weeks ago

This was a great place to stay on Chincoteague. It was centrally located to Assateague and the beach as well as the town. The location was quiet and we really enjoyed our stay.

4.94 out of 5 average rating, 90 reviews

Breeze on Inn

JimRating, 5 stars1 month ago

The house is spotless, clean and comfy. Host is friendly and responsive. The only bad thing was the clock in Livingroom always shows 6:21. But otherwise is perfect. I definitely will stay there again if I'm around the area.