Beach house holiday rentals in Chincoteague

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Top-rated beach house rentals in Chincoteague

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Superhost

The living room features a cozy blue sofa and complementary armchair, arranged around a light wooden coffee table. Decorative cushions with beach-themed text add a touch of charm. The open area leads to a sleek kitchen with modern appliances, promoting a sense of connection throughout the space.

Home in Ocean City

4.76 out of 5 average rating, 25 reviews

Wave Watcher's Condo - Steps to the beach!

Discover Wave Watches Condo! This stunning retreat offers breathtaking views of the ocean and bay, providing an experience of the area's natural beauty. Each room is meticulously designed to offer comfort and style, blending modern amenities with a beach-inspired décor. Enjoy morning sunrises and unwind at night with spectacular sunsets from your private balcony. Ideal for families or groups seeking a seaside escape, Wave Watcher's Condo is your getaway steps to the beach and local attractions!

Top Guest favourite

A renovated home is situated against a vibrant sunset sky, with warm colors reflecting off the exterior. Large glass doors open to the view of the surrounding water. Adirondack chairs are arranged on the deck, offering a space for relaxation outdoors.

Home in Deal Island Historic District

4.97 out of 5 average rating, 69 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.

Guest favourite

Home in Ocean City

4.88 out of 5 average rating, 24 reviews

2 BR Ocean Front Condo w/Pool, Expansive Views

Your family will be close to everything when you stay at this beautiful condo located right on the beach with expansive balcony views of both ocean and bay. With the best amenities around, this year-round rental is equipped with an enormous indoor pool, basketball and tennis courts, shuffleboard, saunas, gym, library, sun deck, & game room with arcades, claw machines, billiards, and air hockey tables. This 2-bedroom unit comfortably sleeps 6 which makes it ideal for families or couples alike.

Superhost

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.

Home in Ocean City

4.79 out of 5 average rating, 19 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!

Top Guest favourite

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

4.96 out of 5 average rating, 26 reviews

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.

Guest favourite

An aerial view showcases a lush landscape with rows of trees lining a pathway leading to the water. The estate is surrounded by greenery, revealing distant waterfront views that accentuate the serenity of the location.

Home in Onancock

4.9 out of 5 average rating, 81 reviews

Historic Waterfront Farmhouse and Cottage

Take advantage of our Off Season reduced rates! - January thru April, 2026. 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 favourite

A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.

Home in Ocean Pines

4.99 out of 5 average rating, 108 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!

Guest favourite

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.

Home in Ocean City

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

Guest favourite

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.

Home in Onancock

4.89 out of 5 average rating, 82 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.

Guest favourite

Home in Ocean City

4.96 out of 5 average rating, 70 reviews

Boardwalk Oasis Incredible Views, Pets Grill Bikes

Book 2 nights, get 1 night FREE stays thru March 10. inquire before booking 24/7 SUPPORT LINEN & TOWELS PROVIDED This 3 bed/2 bath BOARDWALK & OCEANFRONT cottage is your perfect beach escape in Ocean City! Just steps from the sand, this property has all the essentials with some exciting extras to boost! Kayak, grill and house bikes all included! Relax in comfort after a day of seaside fun. Whether you're strolling the boardwalk or enjoying ocean views, this cottage has it all!

Top Guest favourite

The expansive view showcases the sandy beach stretching along the Atlantic Ocean, gently reflecting the clouds above. Features include a shared pool bordered by lounge chairs and landscaped areas. The setting sun casts warm hues over the water, enhancing the serene coastal atmosphere.

Home in Ocean City

4.8 out of 5 average rating, 15 reviews

Oceanfront | Pool | Steps to beach | Elevator

Escape to a premier oceanfront studio with direct beach access! This unique building creates an experience reminiscent of being in a cruise ship stateroom. Perched on the 9th floor this unit offers endless views of the Atlantic ocean and sandy shores as far as you can see. Step outside and enjoy a multitude of beach activities: 🏊‍♂️ swimming 📚reading 🏄‍♂️surfing or paddle boarding 🏖️sunbathing 🪁 kite flying 🏐volleyball 🌊or simply relaxing to the sound of the waves

Guest favourite

A spacious outdoor deck is shown, featuring white lounge chairs and a dining table surrounded by a protective railing. The gray composite flooring complements the coastal atmosphere, while nearby buildings are visible, providing a backdrop to the serene outdoor setting.

Home in Ocean City

4.92 out of 5 average rating, 38 reviews

The Orange Crush - 5BR Beachfront Family Retreat

Welcome to 'The Orange Crush' – a 5-BR Oceanfront Oasis! Sleeps 12, 2 arcade games, shuffleboard, 2 decks with ocean & bay views, smart TVs in every room. If your family is looking for more space. Our sister beach house, Blue Crush is located next door. This house has 3 bedrooms and can accommodate up to 8 guests. Combining your stay at the Orange and Blue Crush, you accommodate up to 20 guests, in 8 bedrooms. Please reach out to us for more details and special group pricing.