Holiday rentals with outdoor seating in Chincoteague

Baywatch North-Waterfront & Roaming Ponies

Calender open for super deals on weekly Summer rentals 2026. Lovely space! 2 queen bdrm unit decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, shared patio cooking area, bbq grill, fantastic view, beach items, plenty of parking, very quiet, out of the way of everything, super laid back host living in the other portion of the house. There is no living room. Labradors and cats on premises, ponies too!

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, kayaking on the 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.

Breeze on Inn

Come relax in our quiet piece of island life. 2 bedrooms (2 full beds) and a sunroom to spread out and relax (2 twin beds). Sleeps up to 6. Assateague beach, wildlife refuge is 5 miles from the house. Lots to do in season and a relaxing getaway off season. Kitchen is stocked with supplies to cook up a seafood dinner if you want a quiet night at home. Bright and cheery living area with cozy bedrooms. Spacious sunroom to relax or socialize. Deck to seat up to 5 adults, bring bug spray in season.

Newly Constructed 2nd-Story Studio Apartment

Our guests can't say enough & pictures just don't do it justice! From the luxury linens & complimentary amenities, we have tried to think of everything! Enjoy a quiet get-a-way just for two or relax with the whole family at this beautiful, newly constructed home located 1/4 mile off Route 13 & less than an hour from area beaches. There are two units with separate outside entrances, but they can be rented together if you need more space. This listing is for the upstairs open studio apartment.

Central Location~Walk to Dining! Beach Pass & Gear

You'll Experience the ultimate in coastal living at your beautifully renovated vacation home, a stone's throw from the Beach road. This is your perfect getaway destination. You'll enjoy a bright chef's kitchen with granite countertops and a tiled backsplash, open-concept first floor with cozy living room, and a convenient half bath. Retire to the second level where 2 bedrooms await, including a primary suite with a private bath & private balcony for sipping your coffee & serene morning views 🌄

Waterfront-CI Bay sunsets-Amazing views

Wide expansive waterfront view of Chincoteague bay-awesome sunsets! 5 waterview rooms. The narrow bit of land across 3446 Main St. belongs to our property w/chairs + a firepit + water access to launch kayaks (2) provided! An open plan-coastal rustic design. Front sitting room w/sofa + high-top table. A large upscale kitchen, two sofas in living room, 2 bdrms, & sleeping loft + a tiny office with a twin murphy bed. Large deck-table, sofa + grill. Family home, not ideal for more than 3 adults.

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!

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.

On a Whim, a family retreat!

Relax with the family at our home, nestled on a quiet private street yet just a short walk from restaurants, beach access, and family-friendly activities. Enjoy access to all that Chincoteague has to offer while retreating to a cozy & comfortable Cape Cod-style duplex. We are a short drive away from exploring Chincoteague National Wildlife Refuge, famous for its wild ponies and hiking trails. Whether you’re here to relax or adventure, this local gem offers something for every nature lover.

Rest A'Shored charming Chincoteague getaway

Spacious open floor plan great for entertaining family and friends with all the modern amenities you need! Eat inside at the large dining room table or enjoy the cool evening breeze outside on the fully screened in porch. 3 bedrooms and 2 full baths can comfortably accommodate 2 families with children or 3 couples. Located on Willow street, you are just a short walk to the Chincoteague carnival grounds and Main Street. We are dog friendly as we know they are really part of the family!

Summer's Sea Shanty on Chincoteague Island

Summer's Sea Shanty is a delightful Chincoteague coastal cottage that’s perfect for couples, families, or small groups of friends. We've worked hard to make this the ideal modern day beach retreat. This home boasts screened in front and back porches, a fire pit, an open/functional floor plan. We're pet and kid friendly with luxury linens and rugs and dish ware... We're proud to be the best of the best on the island. We're centrally located and minutes from Assateague National Seashore.

Chincoteague Island Creekside Cottage

Creekside Cottage delivers all the feels... July 2020 USA Today "Best Coastal small town". Private dock off large back yard for crabbing or catching the sunset, minutes away from the Chesapeake Bay and Historic downtown, 10 minutes to Chincoteague National Wildlife Refuge (Ponys) and the Beach (golf cart friendly). Everyone can hang on the huge sectional in the eve and play board games or catch up. Smart TV, Wifi, Large cooks kitchen (dbl oven), Table extends to 124". Make Memories!