Beach house vacation rentals in Chincoteague

A wooden deck with multiple sitting areas features stairs leading down to a sandy area with greenery. Sunlight illuminates the space, and a large umbrella provides shade atop the deck. The backdrop includes large windows of the house and a clear blue sky.

4.96 out of 5 average rating, 70 reviews

Relaxing Breezy Seaside 3bd/2ba/2decks King Bed

Wake up to stunning ocean views and the soothing sound of waves at this charming beachfront home. Relax on the breezy indoor and outdoor living decks. Enjoy recently updated stainless steel appliances, quartz countertops, and a fully tiled walk-in shower. The primary bedroom has direct access to the oceanfront deck, with ocean views in every bedroom. Nearby: Jolly Roger Amusement Park Boat Tours & Fishing Jetski & Parasailing Need more space? Rent the sister house next door! Message for details.

Home in Deal Island Historic District

A sunlit florida room showcases large windows that allow views of the surrounding landscape. Comfortable seating is arranged around a central coffee table, with a dining table positioned nearby. A nautical-themed rug adds a touch of charm to the serene atmosphere.

4.97 out of 5 average rating, 66 reviews

"Promise Point" Bay front home with dock. 3BR 2BA

Take it easy at this unique and tranquil getaway. Open floor plan home completely renovated in 2022. Surrounded by water on 3 sides with dock access and neighbors a community beach and boat ramp. Great place for fishing, crabbing, boating, jet skiing, kayaking or just relaxing by the fire pit. 3BR 2BA with florida room surrounded by large decks, full kitchen with quartz countertops, washer and dryer, sleeps 12, 1 queen BR, 1 Full BR, Triple Bunk BR, queen Sleeper, futon, and twin roll away bed.

4.97 out of 5 average rating, 58 reviews

A scenic collage features various images: a tranquil beach sunset, a lush golf green with a white sand trap, a wooden pier stretching over gentle waves, wild horses running along the shore, and a charming screened porch nestled among tall trees.

Home in Ocean Pines

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.

Welcome to Bliss at the Beach, our charming 3br, 2ba home nestled in the desirable, beloved Ocean Pines community. Loved for its safe, quaint, family friendly neighborhoods. Find yourself less than 15 minutes away from the beautiful beaches and vibrant shopping, dining and boardwalk district of Ocean City. Enjoy the ease of the prepaid parking at the Ocean Pines Beach club on 49th street, just unload the family and walk on the beach!! Summer months Bliss is a 7-night minimum to guests 25+old

A spacious outdoor deck features cozy seating arrangements and a coffee table, with ocean views visible beyond. Relaxing chairs are positioned around, while the sparkling coastline and beach access paths are displayed in the background.

5 out of 5 average rating, 8 reviews

NEW!OceanView-Pool-Sundeck-Bike-Theater-Game Room

Welcome to Your Elegant Oceanview Escape Home Experience the perfect blend of upscale comfort and family-friendly amenities in this spacious 5-bedroom retreat designed to host unforgettable getaways. Overlooking the sparkling coastline, steps from the beach, this home sleeps 16+ and offers everything you need to relax, recharge, and reconnect. Highlights • Breathtaking ocean views from multiple decks • Pool and sundeck (Pool closes Sept 29th 2025) • Arcade/game room • Outdoor movie deck!

An aerial view captures a sprawling waterfront estate, encompassing lush greenery and winding waterways. White houses are nestled amongst the trees, with clear open spaces leading down to the water's edge. The landscape is dotted with small islands, providing a serene and natural setting.

4.9 out of 5 average rating, 80 reviews

Historic Waterfront Farmhouse and Cottage

Take advantage of our Off Season reduced rates! - September thru December, 2025. Pets are always welcome with a reasonable fee This secluded 27 acre Waterfront estate is a classic Eastern Shore Farm with an adjacent optional cottage. This estate features brilliant water views from every room, with kayaking, swimming, fishing, crabbing and oystering. This secluded Mattapany Farm offers a vacation that gives the best that the Eastern Shore of Virginia has to offer with a relaxing atmosphe

Top guest favorite

4.97 out of 5 average rating, 65 reviews

Hot Tub & Pool Table Waterfront Home | 4King Beds

Yes- Linens are included! (Bed sheets & bath towels) New pool table & jacuzzi!! Experience the ultimate Ocean City getaway this year, with unbelievable water views from every room & a private two-story wrap-around balcony. Enjoy 4 comfy king beds. The home is perfect for groups seeking relaxation & home away from home. Only 4.2 miles from the Ocean City Boardwalk! What else is included? Bonfire pit Parking area Shampoo-Conditioner-Body Wash Soaps Laundry Detergent Kayak Beach chairs

4.96 out of 5 average rating, 26 reviews

The exterior of the home features a welcoming entrance with a covered porch and decorative seasonal wreath. A stone pathway leads to the front door, surrounded by lush plants and landscaping, framed by light-colored siding and a garage door.

Home in Ocean Pines

Robin Hood Retreat

Explore the Eastern Shore from this beautiful Ocean Pines home with 4 King Bdrms, 3 1/2 baths. Bring the whole family for a couple's week to enjoy the local sights. Full Kitchen, DR, LR, FR, Sunroom, Deck & Patio on a quiet residential street. Berlin, the OC Boardwalk & Assateague Island are minutes away for a fun filled day. Amenity filled The Ocean Pines Community with pools, golf, tennis and food & live entertainment. Must be 25 or prior service military or first responder to rent.

Top guest favorite

Home in Ocean Pines

4.99 out of 5 average rating, 97 reviews

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

Superhost

A serene ocean view stretches across the horizon, reflecting the sunlight on the calm water. Sandy beach lines the shore, complemented by natural dunes and sparse vegetation. The image captures the inviting atmosphere from a balcony railing, promoting relaxation and a connection with the surrounding environment.

4.74 out of 5 average rating, 43 reviews

“The Pelican’s Perch”

Spacious one bedroom condo with a great ocean view. Best ocean view in the building! Nice balcony to enjoy coffee & watch the waves & pelicans fly by. The building has an indoor pool and family game room. Large outdoor lounge area with picnic tables & view. Walking distance to north side park, great restaurants and entertainment. Beach is obviously right there to enjoy and parking is on location in private lot under cover. Dogs are permitted but only from Oct 1 thru April, off season

Superhost

A metal tray filled with freshly steamed crabs sits on a wooden table. The crabs are coated with seasoning and display vibrant orange-red shells. In the background, natural light filters through a screened porch, adding a warm ambiance to the scene.

4.88 out of 5 average rating, 76 reviews

Escape To A “True” Chesapeake Waterfront Property!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Bayview House", an updated 1950's cape cod featuring lots of original features with many modern upgrades. It sits on our 44-acre property along with our "Sunset House" - also available on Airbnb.

A large waterfront estate is viewed from a distance, framed by tall trees. The house features a wraparound porch with blue rocking chairs, surrounded by expansive green lawns. The soft glow of sunset casts elongated shadows on the ground, enhancing the serene atmosphere.

4.96 out of 5 average rating, 90 reviews

Chesapeake Bay Retreat | Private Dock + Beach

Wake up to sunrises over the creek as you sip your morning coffee and soak in the stillness that surrounds you. 🌿 Outdoor Features: Private dock with multiple boat slips – ideal for crabbing, fishing or just taking in the view Covered porch with a fireplace, tv and gas grill Outdoor fire pit for s’mores in summer or oyster roasts in winter Private beach area for lounging, shell collecting 🎯 Yard Games for All Ages: Hammock for afternoon naps beneath the trees

Superhost

A serene waterfront scene showcases tall trees silhouetted against a vibrant sunset sky with hues of orange and yellow. The calm water reflects the colorful sky, creating a peaceful ambiance. Several outdoor chairs are visible near the water's edge, inviting relaxation.