Family-friendly holiday rentals in Chincoteague

Maggie’s Cottage on Poplar - Our Happy Place!

Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

Island House: Kayaks, Bikes, Beach Gear & Firepit

Welcome to Happy Ours! Relax with the whole family at this peaceful Chincoteague home. Walk to the park (Pony Swim!). This beachy cottage offers all the charm with plenty of space, in a quiet area with a huge property. This is a family home that we enjoy with friends & family year-round. We would love to share that experience with you! If we can do anything to make your stay more enjoyable, don’t hesitate to reach out, and please kick back and relax and enjoy all that Chincoteague has to offer!

Bell Farm Cottage Quiet, Tranquil and Peaceful

Cozy cottage located on a quiet backroad overlooking a wide open field with a deck that provides warm & sunny space for relaxing or reading a book. BFC has a warm farm house feel w/ a touch of the beach. Our kitchen is fully equipped w/ all you need to cook. BFC is located only a few miles from both seaside and bayside boat ramps. A 5 minute drive to Onancock, Walmart, YMCA, shopping & many local shops for just the right souvenir. Wachapreague, Wallops & Chincoteague are just a short drive away.

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.

Pearl in the Pines: bikes, kayaks, EV charger

Nestled in the shade of tall pine trees in the private community of Oyster Bay, "Pearl in the Pines" is a charming coastal retreat equipped to meet any need. This bright and beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly, making it an ideal space to vacation with your entire family. The spacious screened porch offers the perfect perch to savor your morning coffee with the sunrise or relax with friends and family while enjoying fresh, locally sourced seafood.

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!

Private Country Beach Retreat

Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

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!

Baywatch Upper-Waterfront & Roaming Ponies!

Beautiful space in and out! Vacation efficiency, 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. This is the entire upstairs of the house, full staircase to get up to the second floor.

Adorable Beach Cottage Just Steps From Town & Bay

Escape to Wiggle Bay, a darling 1955 2 BR sunny 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! Perfectly located on a quiet street, just steps from local shops, a coffee house, and the waterfront park, where you can watch the boats, enjoy the sunset and feed the ducks. Just 2.3 mi to Assateague Seashore/Chincoteague Refuge. Ideal for a peaceful and convenient getaway!

"Jolly"- Houseboat Getaway

"Tiny house on the water"! Jolly is a 42ft Holiday Mansion. Baywater Landing buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & deck areas to enjoy! 35 mins from Ocean City & Assateague Island. 45 mins from Chincoteague Island. Jolly remains docked, but guests have access to kayaks and paddle boards at no additional charge. Baywater Landing is secluded- some even say "boring"- but we think that's the whole point!

Key Lime Cottage

Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Key Lime Cottage at the Key West Cottages resort offers views of the Chincoteague Bay, giving you a front-row seat to the breathtaking sunsets that Chincoteague offers each night. This one-bedroom private cottage includes a master bedroom with two queen beds, a fully equipped kitchen, living and dining space, waterfront deck and access to many amenities!