Vacation rentals with a pool in Chincoteague

SeaGate Serenity | Oceanfront Condo with Balcony

Wake up to the sound of the waves crashing outside your window and finish your days relaxing on the private balcony as you watch the pastel skies over the ocean at sunset. Come find your serenity by the sea in our newly renovated oceanfront condo. Located in midtown, you can keep your car parked in our reserved spot and walk to many of the towns best restaurants, bars, and entertainment as well as the World Famous Ocean City Boardwalk. Morning beach strolls, pool days, and evening sips await :)

Oyster Cottage

Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Oyster Cottage at Key West Cottages offers expansive panoramic views of the Chincoteague Bay, giving you a front-row seat to breathtaking Chincoteague sunsets. This two-bedroom private cottage includes a master bedroom with a king bed, second queen bedroom, fully equipped kitchen, living and dining space, tiled walk-in shower, wrap-around deck, and more. You can fish, crab, and even dolphin watch right from your balcony!

Nature's retreat @ the Bug-a-Boo. Beaches nearby

We're inside a lovely gated campground community with full amenities @ the Club House: Wi-Fi, pool, fishing n crabbing, boat ramp, laundry, and bath houses. The Bug-a-Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 20 miles from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

Anchors Away, Your Dream Getaway in Fenwick Shoals

Escape to our stunning, spacious 5-bedroom, 3.5-bathroom retreat in a gated community just 2.5 miles from the Fenwick Island/Ocean City beaches, nearby golf courses too. Our 3 story single family home sleeps up to 13. Over 3500 square feet, our house features a fully equipped kitchen, LR/DR, optional elevator, game room with pool table, slot machine, foosball, air hockey & more. Our beautiful single family home with the perfect blend of comfort & coastal charm the whole family will enjoy.

Modern coastal beach home in West Fenwick Island

Welcome to Two Buoys At The Beach, a bright and beautiful open-concept home just 7 minutes from feet in the sand at Fenwick Island State Park. Our family-friendly beach house comfortably sleeps 10, with plenty of space to relax and unwind. Entertain with ease with a fully stocked kitchen, private gas grill, and furnished deck, and enjoy the outdoor shower after a day of fun in the sand or at our community pool. We hope you enjoy the quiet serenity of the Delaware beaches as much as we do!

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

The Puskar’s Landing

Centralized to the beaches of Assateague Island. In the heart of Worcester County. Off the country roads of Maryland’s Eastern Shore. This cute rancher sits one mile from Chincoteague Bay with public boat ramps, a beach and pier. You can boat or drive approximately thirty minutes to Ocean City or Chincoteague Island for food and fun. This spacious property has plenty of green space for kids to run and play, enjoy the hot tub to unwind. Enough space to bring a boat or camper if needed.

Farmhouse located on a horse farm

Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Sunset Bay Villas 219 waterfront condo

Amazing views- Welcome Bird Watchers, Nature and Beach Lovers! Designer condo with direct views of the Intracoastal Waterway Chincoteague Channel and Wallops Long term rental from October-May with government per diem per person and special offers for long term occupancy. Max. occupancy per Chincoteague town fire code is 8. This includes adults, children (2 and older) and infants (children under two). Government ID issued required to be shown on or before check in date.

Cedar Gables - Waterfront, Pool, Hot Tub, Dock

Just a few miles from Chincoteague National Wildlife Refuge & Assateague Island Beach, Cedar Gables has everything you are looking for in a Chincoteague Island home! Enjoy the ease and convenience of a central waterfront location. Each bedroom has a seasonal fireplace & private bath w/ deep tub. Lounge outside by the private pool (seasonal), hot tub (year-round) & tiki-bar in screened atrium. Private, deep water pier & boat dock is perfect for crabbing & fishing.

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU

BEFORE BOOKING: Pool will be open 4/05/26 Unless PRIOR AUTHORIZATION….. NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your party are allowed on the property. Fully restored top to bottom 1920s farm house. Every bedroom has its own full bathroom Full laundry room with extra refrigerator RH furniture All bedding/towels/paper towels/toilet paper/body wash/shampoo/conditioner/spices/laundry detergent included;Total turn key

Oceanfront Family Oasis: Pool, Beach & Parking!

Escape to your dream family vacation in this amazing 2-bedroom condo on the 8th floor! Enjoy incredible ocean views, direct beach access, and proximity to Ocean City's top attractions like the vibrant OC Boardwalk and thrilling amusement parks. This condo offers modern amenities, a refreshing seasonal outdoor pool, and the convenience of free parking. Perfect for families seeking fun and relaxation near the ocean.