Beach house holiday rentals in Chincoteague

Starboard on McKeil Point, w/heated pool & hot tub

Starboard on McKeil Point is a beautiful 5 bedroom, 3.5 bath private waterfront home on five acres overlooking the wide water of Fishing Creek - the perfect compound for families & groups. The house features water views from every turn. Outdoor amenities include a generous screened-in porch, a private dock, a sandy beach, a heated salt water pool & a hot tub. There is also a one bedroom apartment on the second floor of the carpenter's barn which sleeps 6 and includes a full bath and kitchenette.

"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.

Summer Breeze waterfront new home-Private Beach

FALL AND WINTER RATES AT UP TO 50% OFF-HURRY! Summer Breeze, located on the Chesapeake Bay in the fishing village of Reedville, is our new 3 Bedroom, 2 Bath home with waterfront shoreline and beach on a peaceful cove. The neighborhood beach, which is for residents and guests renting, fronts directly on the Chesapeake Bay and is just a few lots, and a short walk away. The gentle Bay beach with soft sand, gentle waves, and gently sloping bottom are perfect for fun and play for the whole family!

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

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!

Historic Waterfront Farmhouse and Cottage

Take advantage of our Off Season reduced rates! - September 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

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.

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!

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.

Ocean-front getaway, amazing views, dog friendly!

Perfect getaway to the ocean in this updated, stylish home. Elevated ocean-front, with stunning views from every room and two private balconies. Amazing location - walk to great restaurants and still enjoy a private-feeling beach with lifeguard stand just steps away. No need to 'pack' for the beach -the house is just steps away. Enjoy coffee at the granite island overlooking the beach! There is a set of stairs up to the condo, and another set of stairs up to the main bedroom.

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

Waterfront, Private Pier, Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure for everyone. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!