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!

The Boathouse: Charming & Historic Waterfront Stay

Welcome to the Boathouse! You read that right: Boathouse (not House Boat!) This house, which has been part of our family for generations, is the perfect home-base while you visit the special island of Chincoteague! Watch the lighthouse from across the marsh, go for a canoe ride through the channel, catch some crabs off the private pier, or make your way to the famous Assateague Beach - this cozy, quirky house is perfect for those seeking a unique and memorable adventure on Chincoteague Island!

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.

Hot Tub. Fire pit. Fenced Yard. Games. Downtown.

Mermaid & Mare – A Downtown Retreat with Hot Tub, Firepit & Pet-Friendly! Escape to an island retreat with two spacious bedrooms, each with an en-suite bath. First-floor bedroom – King bed, walk-in shower, deck access with hot tub. Upstairs bedroom – Jacuzzi tub, balcony with bay views. With 4 beds (1 King, 3 Queens), there’s room for family & friends. Amenities: Hot tub, firepit, cornhole & pet-friendly backyard, Smart TVs, screened porch, & bay-view decks. Walk to restaurants, bars & shops.

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!

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!

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

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!

The Magnolia House ~Availability in July~

You and your family will love this 100 year old fully restored home with its original hard wood floors, brand new chef’s kitchen, the 75’ TV and the extra large couch. Plan to pack your beach towels, your favorite swim suit and make yourself at home here in our Magnolia House. Located only 2 blocks from Maddox and only 5 miles from the beach. The bike trail to the beach starts right in our backyard. We hope to have created a space you can’t wait to come back to.

The Cottage Bluefish -newly remodeled for '26

Looking for the quintessential Chincoteague island retreat to make lasting memories? Welcome to COTTAGE BLUEFISH, a Chincoteague Island hideaway lovingly restored and newly available for the 2026 rental season. This island cottage offers classic Chincoteague seaside look & vibe, combined with fresh, clean, newly remodeled everything. Discerning guests will not be disappointed. Fresh bedding and linens are provided.

Summer's Seaside Cottage | Near Ponies & Beach

Welcome to Summer's Seaside Cottage -- a breezy, costal retreat designed for slow mornings, salty air, and unforgettable island evenings on Chincoteague Island. Where you're here for the wild ponies, beach days, or simply to unwind, this is the kind of place that instantly feels like a vacation.