Holiday rentals with a patio in Chincoteague

Bradley's Bayou

Welcome! Visit our quiet secluded neighborhood 20/25 minutes from Rt. 1 restaurants, beaches & outlets. Our waterfront home has beautiful views & reasonable prices. This is a boating & crabbing community with a community pool, tennis courts, crabbing docks & playground. Fun & easy walking and biking for families! Bring creek boots! NOTE: Linens/towels NOT provided. Bring your own! Or Rental suggestion: Sheets at the Beach, LLC 2025 Pool info: schedule in "add'l photos" No smoking/ No pets

Turtle Cottage by the Bay

Welcome to our Turtle Cottage by the Bay!! Escape the hustle and bustle and enjoy our gated community where you can take long walks, bike rides, enjoy the Community Pool, Pickle Ball, Crabbing, Fishing or Kayaking. Close to Beaches and State Parks. We are also very close to MANY Amazing Restaurants, Super Cool Breweries and Outlets for Tax Free Shopping. Perfect for that Romantic Getaway, Friends Trip or Family Vacationing!! Kids Play Travel Ball? We are just 12 Miles from Sports at the Beach.

Blue Loft in the Sky on CI

This 900-square foot open floor plan loft has been throughly planned, designed, and custom-built by the owner. THE LOFT IS ON THE PONY PENNING ROUTE and within walking distance of Chincoteague's popular Seafood Festival and Oyster Fest. You'll find all the comforts of home including full linens, a fully stocked kitchen, smart tv, cozy inviting living room sofa, sitting area, etc. The loft is completely open living space allowing the family make life-long vacation memories on Chincoteague Island!

Bayfront Oasis Vacation Rental

Waterfront panoramic views with a crabbing dock and boat slip. 4 bedrooms (full/twin bunkbeds, 2 twin beds + full bath, queen bed + full bath, king bed + full bath, and sleeper sofa in living room); up to 14 guests. Additional features include ½ bath, sunroom, living room, kitchen, laundry room (washer/dryer), and gaming room. Outdoor space with dining table, outdoor kitchen, firepit, gazebo, cornhole. Resort amenities; swimming pool, bikes, playground, pickleball, dog park, marina, store.

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

Relaxing Bethany Beach Retreat, Pools, Dogs OK

Welcome to your new happy place. Just steps from the bay and minutes from Bethany Beach, the home has everything you need to unwind and relax. Community has amazing amenities including indoor/outdoor pool, game room, hot tub, and fitness center. This retreat is the perfect getaway for adults (close to beaches, great restaurants, and shopping), children (board games and game room), and your furry little friends (dog-friendly beaches and trails). Perfect for families small and large!

El Ancla

stunning bay sunsets and idyllic outdoor space at this peaceful waterfront home in prime 94th street location with amazing breeze. Recently rehabbed - new hardwood floors, bathroom, and brand new interior and exterior furniture. Bayfront deck with your own boat slip. Brand new casual comfort deck furniture. Remote work with a view! 10 min walk to beach, playground, community arts center, mini golf, bars. Beach chairs included. We can provide pack n play upon request

cozy sunset cottage

Feel at home as soon as you walk in. Indulge in a coastal retreat that embraces you with a beach-inspired ambiance from the moment you arrive. Experience the carefree comfort of this centrally-located home, thoughtfully designed to exude a beach-like charm. And don't miss the special touch—an inviting screened-in outdoor lounge area where you can relax, unwind, and soak up the coastal vibes, creating cherished moments reminiscent of blissful days by the shore.

Beachy Sunset Island Townhouse!

Located in the heart of Sunset Island, this 4 bed/4.5 bath townhouse is steps away from the clubhouse and bay. Beautifully decorated and suitable for families, this home even includes baby gear and a crib so you don't have to bring anything with you. Relax on Sunset Island's private beaches and never leave the community. Everything is available at your fingertips for an unforgettable stay. With 2,400 square feet of living space, there is room for everyone!