Holiday rentals with a pool in Chincoteague

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Berlin Beach House, near Ocean City & Assateague!

Close to everything when you stay at this newly renovated vacation home in historic Berlin. Big yard, lots of parking, & walking distance to downtown Berlins restaurants, breweries, grocery, & more. 10 minutes to the beaches of Ocean City Maryland or Assateague Island wild horses. Arcade games and bikes added for 2025 season. Above ground pool open Mid May - Mid Sept. 2 washer & dryers. Locally owned managed and cleaned for a worry free stay. All linens and bath towels provided.License#2023-3

Island Creek Retreat - Great Views, Pool, Pier

Just a few miles from Chincoteague National Wildlife Refuge & Assateague Beach. Beautiful marsh & wetland views. Shared private pier is perfect for crabbing & birdwatching. Great location - walk or bike to shops, restaurants, water park & much more! Spend the day at the shared private pool. This 2nd floor unit has a bedroom w/ king bed, kitchenette with 2 burner stove top, microwave, & full size fridge. Spacious living room w/ queen sleeper & desk. Access the full bathroom from the living area.

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.

Pool/HotTub/RecRoom/Pvt. Dock YearRoundPlayground

Discounts Offered! Enjoy best of Eastern Shore living in this unique waterfront retreat offering FULL privacy on 8+ acres! Newly renovated 3BR/2.5BA home blends nature, comfort, & resort‑style amenities PERFECT for families & groups in ALL seasons: *Large Swimming Pool & 7-person Hot Tub *Detached Rec Room w/Pool Tbl *Shaded Outdoor Grill/Sink/Fridge *Private Dock for Fishing/Kayak *W/GOLFING, BEACHES, & HUNTING nearby! Escape the city rushes & don't miss out on Insta-worthy pics! BOOK NOW!!

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.

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season

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.

Bayfront | Pool Open & Heated, Hot Tub, Dock, Pets

Welcome to The Fleeton House – a serene waterfront retreat perfect for families, friends, or groups! This spacious home offers 6 bedrooms, 3.5 baths, a heated pool, hot tub, private pier, and more. Kids and pets are welcome, and there's plenty of space to unwind, dine, and play. Come for the views, stay for the memories. Shell Landing Public Boat Ramp (2 Mins) Downtown Shops & Restaurants (6 Mins) Reedville Attractions (6 Mins) Waterfront Dining (6 Mins or Less)

Key Lime Cottage

Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Key Lime Cottage at the Key West Cottages resort offers views of the Chincoteague Bay, giving you a front-row seat to the breathtaking sunsets that Chincoteague offers each night. This one-bedroom private cottage includes a master bedroom with two queen beds, a fully equipped kitchen, living and dining space, waterfront deck and access to many amenities!

Private pool, waterfront, kayaks, bikes, firepits!

The Golden Quarter Farm is 150-acre waterfront, nature preserve, centrally located 5 miles from Assateague Island and its wild ponies, small town charm of Berlin, and OC Boardwalk. With a pool, kayaks, SUP, hiking trails, bikes, and birding, there's little reason to leave the property! Please note: Max of 8 adults. No parties. No Pets. Renters must sign a Rental Agreement. Pool open May-Sept 30th isn't heated.