Holiday rentals 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

4.83 out of 5 average rating, 101 reviews

Cottage in Chincoteague

"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!

4.99 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!

4.97 out of 5 average rating, 167 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.

4.87 out of 5 average rating, 131 reviews

Houseboat in Snow Hill

"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.

4.86 out of 5 average rating, 189 reviews

Flat in Chincoteague

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.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Bungalows

Intimate homes, inviting architecture

Popular amenities for Chincoteague holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chincoteague

4.93 out of 5 average rating, 28 reviews

Cabin in Chincoteague

Nor’easter - water view - recent renovation

JoelleRating, 5 stars3 weeks ago

Jess' place was perfect for our stay. With easy access to beach and to all the main attractions. We cooked several meals in the kitchen it was well stocked.

4.72 out of 5 average rating, 100 reviews

Cottage in Chincoteague

SNUG HARBOR waterfront cottage with a grand view!

AlexandraRating, 5 stars3 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.

4.99 out of 5 average rating, 71 reviews

Bikes-Kayaks-Outdoor Shower Grill-Firepit-Beach Eq

LorraineRating, 5 stars2 weeks ago

This place had a great location; it was less than 10 minutes for the local restaurants and only a 15 drive to the beach. The kitchen had everything you needed, there was plenty of space for atleast 6 people (even though there was just the two of us). The airbnb itself was really charming. Host was amazing, really responsive and communicative. Their checkin and checkout procedures were really clear. My only “asterisk” is that since it is an older house and in the middle of a marshland basically, it was pretty humid inside. It seems normal for the area especially considering it was raining half of our stay. The AC boxes in every room definitely helped but just something to note about our stay. I’d recommend a dehumidifier to the hosts. Overall a great stay, would recommend this place to all when staying in Chincoteague!!

4.93 out of 5 average rating, 58 reviews

Cabin in Chincoteague

The Boathouse: Charming & Historic Waterfront Stay

ThomasRating, 5 stars3 weeks ago

The Boathouse is such a wonderful place to stay. It is so unique and has an abundance of charm. The beautiful setting overlooking the marsh from inside and on the deck is incredible! We had a fantastic time at this lovely place and the beautiful surrounding area as well. Christian and Ashling were fantastic hosts with timely and responsive communication and great recommendations for you to do during your stay. We highly recommend the Boathouse!!!

4.98 out of 5 average rating, 49 reviews

cozy sunset cottage

ZaneRating, 5 stars1 week 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!

4.96 out of 5 average rating, 85 reviews

Flat in Pocomoke City

Pansy’s Retreat

TinaRating, 5 stars1 week ago

Pansy’s retreat was perfect for my husband and I and our infant son. It was quiet, clean, plenty of space, and pretty close to chincoteague. We loved it, and we had a blast. When we arrived all the outlets were covered and the pack and play crib was already set up which was such a treat, we really appreciated everything!

Apartment in Chincoteague

4.9 out of 5 average rating, 21 reviews

3 Mi to Beach: Waterfront Condo in Chincoteague!

SteveRating, 5 stars2 weeks ago

First of all, this place was spotless. You want great scenery, lots of wildlife, peace and quiet? This is your place. Perfect for a single traveler, couple or small family. Was my first time in Chincoteague and I had a great time. Absolutely loved this stay!