Fitness-friendly vacation rentals in Assateague Island

Come enjoy Summer on Smith Island at the HH Ranch

Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Updated enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. New front deck. Large bathroom with dual rainhead shower. Easy access to the water. Bikes and SUP available in the shed. Kayaks are covered outside by shed. Island is only accessible by boat. Enjoy the tranquility of this unique place.

2BRCapri: Indoor Pool, Game Room, Massage Chair

ALL THE COMFORTS OF HOME AT THE BEACH! BRAND NEW RENOVATED BATHROOMS! -ALL LINENS INCLUDED -Comfortable electric-reclining sofas -65-in smart Roku TV with soundbar. -Massage chair in master bedroom -Balcony & Dining Area w/ Ocean +Bay Views -In-unit W/D -Many conventional & USB Outlets -Arcade level features b-ball hoop, pool tables, ping-pong, shuffleboard, air-hockey -Outdoor tennis court -Large heated indoor pools -can swim full laps -Sauna and Gym -Board games in unit -Fast Wifi

Charming Getaway Golf Simulator

4 bedrooms plus a Bonus room and bunkroom with 3.5 Bathrooms Escape to our cozy rental in Berlin, Maryland, just minutes from the charming downtown of "America’s Coolest Small Town." Perfect for families, friends, or golf enthusiasts, this home offers relaxation and fun in one unique package. Golf Simulator: Enjoy a state-of-the-art indoor golf experience, rain or shine. Located near Ocean City beaches, Assateague Island, award-winning golf courses, and downtown Berlin. Book your stay today!

Bayside Family Oasis - Perfect for Large Families

Welcome to your coastal getaway in Bayside Resort, less than a 5-minute walk to the Sunridge Pool and fitness center. Set along the 17th hole of a Jack Nicklaus golf course, this spacious 5-bedroom home sleeps up to 12 guests and is ideal for families, golf trips, and group getaways. Inside, enjoy an open-concept layout with a fully equipped kitchen, dining area, and fireplace, perfect for relaxing after the beach or pool. Step outside to unwind on the patio with golf course views.

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.

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.

2-Bedroom Oceanfront – Pool, Xbox, Pickleball, Gym, Wi-Fi

Wake up to panoramic ocean views at Blue Wave, a newly renovated 2BR/1.5BA oceanfront condo in the premier Golden Sands Resort! Sleeps 6 with king bed, queen bed, and queen sleeper sofa. Enjoy your private balcony, indoor & outdoor pools, private beach, fitness center, game rooms, tennis, pickleball, and seasonal tiki bar. Relax with a Smart TV + Xbox Series S with Gamepass! Steps to the beach, close to Northside Park, great restaurants, and the Ocean City Boardwalk!

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

Serene Family Getaway | OC & Assateague Adventures

Coastal fun awaits! This 3BR, 2.5BA townhome in The Landings at Bayside is minutes from Ocean City, Assateague, and downtown Berlin. Enjoy pools, a playground, sports courts, crabbing pier, and kayak launch. Bikes, beach gear, and surf spots nearby—plus local favorites like Sinepuxent Brewery and the Assateague Island Surf Shop. Perfect for families, friends, and adventure seekers! EV charger in garage.

Eagles Nest- (Water View)

Home built in 2023. Local beach. Relax at this unique and tranquil getaway. Beautiful sunsets, water view, 3 decks, kids area, outdoor patio & pergola, outdoor Shower Feed and watch deer from back deck. Close walking distance to carnival grounds and pony auction. The house list occupancy of 5, however, there is a futon on bottom floor that sleeps 2 more comfortably.

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED 8TH FLOOR PENTHOUSE! This stunning top floor 3 b 2.5 ba unit is the ULTIMATE friends & family beach trip, located in a premier building in Ocean City. Enjoy the ocean breeze and stunning views from over 150 square ft of private balcony. Wake up to ocean views from every room!

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.