Vacation rentals with a pool in Chincoteague

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!!

Eastside Oasis: Heated Pool + Pond + Patio!

This Modern Farmhouse home features six spacious bedrooms (five KING bedrooms and one with two queens ALL with en suite bathrooms) so nobody has to fight over who gets the nicest room on your vacation! :) There's a fully stocked chef's kitchen, plenty of seating, and sliding glass doors that open to the outdoor space with views of the pool, pond, and fields. You'll see lots of wildlife on the property including deer, turkeys, geese, lots of waterfowl. Come stay for a unforgettable vacation!

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

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

The Big Chill at Bethany Beach

The Big Chill at Bethany Beach is our whimsical family beach house in the Clearwater community, just two miles from the Bethany Beach boardwalk. We've thought of everything so that you don't have to. Spacious bedrooms with fine bed and bath linens; fully stocked kitchen with cookware and spices; smart TVs and Nintendo Switch; lots of books and board games; screened-in porch and open-air deck; and comfortable furnishings throughout. And bring your dogs; they're family, too!

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.

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!

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

BEFORE BOOKING: Pool will be open 4/05/26 NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your reservation 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

Bayfront Modern Retreat • Dock, Kayaks, Views

Wake up to shimmering Chincoteague Bay views in this modern waterfront escape on Virginia’s Eastern Shore. Spend mornings on the water, afternoons by the fire pit, and evenings under glowing sunsets. Kayaks, bikes, pools, golf, pickleball, and trails are moments away, with beaches a short drive. Bring the dog, unplug, and settle in. Your coastal reset starts here.