Fitness-friendly vacation rentals in Chincoteague

Luxe Estate w. GameRoom-HomeGym-FirePit-BBQ-WetBar

Escape to The Manor at Brooklyn Meadows, a luxury 6-bedroom retreat on a 40-acre equestrian estate. This home is perfect for family vacations and group trips, featuring a private pool, game room, fire pit, BBQ and home gym - all surrounded by rolling horse pastures & peaceful country views. 🛍️ 7 min to Berlin – “America’s Coolest Small Town” 🌊 10 min to Ocean City beaches & golf courses 🐴 15 min to Assateague Island & its wild horses Stay with us & experience the best of MD's Eastern Shore!

Love Above the Waves-Best Ocean View & Heated Pool

🥂 Complimentary champagne, wall-to-wall ocean views, breathtaking sunrises, and warm swims or barefoot beach strolls—your romantic escape begins here. Whether you're celebrating a birthday, anniversary, engagement, or simply falling in love all over again, Love Above the Waves is more than a stay—it's a shared experience, both intimate and enduring. Let the ocean be your witness, the champagne your spark, and the sunrise your reminder: some escapes aren’t just romantic—they’re unforgettable.

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!

Bright Open Floor Plan Family Beach Retreat

Everything you need to enjoy your time in Bethany! Our family home is a bright beautiful retreat to relax and enjoy yourself. Located on the 1st tee of the Salt Pond Golf Course. Community Pool & Gym just a two minute walk! Basketball, Tennis, Shuffleboard, Sand volleyball court, and Children's Playground access included. Grocery Store & Restaurants at entrance to the neighborhood (2 min drive or a 10 min walk!) Just minutes drive to multiple beaches, shopping, restaurants & family fun!

Ocean Pines 2BR 1BA Cottage with Fire Pit

Pint-sized, pet friendly cottage close to everything, the perfect, quiet little sanctuary. Full kitchen in case you wish to cook in one night. Dining table and a cozy living room. Board games, yard games, pickle ball equipment, outdoor seating, fire pit and a grill round out this amazing cottage. Accommodates 6 people, recommend no more than 4 adults. Close to the Woodlands Restaurant & the Pines Public House. Not far from the Ocean Pines Sports Core Pool and the Ocean Pines Golf Club.

Stay Salty OC Beach House

Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

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.

Waterfront Chincoteague Island

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.

Oceanfront 2 Bed/1.5 Bath, Balcony, Pools, Lounge

Wake up to breathtaking ocean views at Driftwood, a beautifully remodeled 2BR/1.5BA oceanfront condo in the amenity-rich Golden Sands Resort! Sleeps 6 with 2 queen beds + queen sleeper sofa. Enjoy your private balcony, indoor & outdoor pools, private beach, fitness center, game rooms, tennis, pickleball, volleyball, huge sun deck, and seasonal tiki bar. Steps to the sand and close to Northside Park, top restaurants, and the iconic Ocean City Boardwalk!

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

BEFORE BOOKING: Pool is open as of 04/5/25 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

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities

Welcome to our 2 bedroom 2 bath ocean front unit at the Carousel. We take care of this condo ourselves to ensure you have a comfortable, clean and well stocked place to stay. This unit sleeps 6, one king bed, one queen bed and one queen sofa bed. There is an ocean front balcony & a bay view balcony. Washer & Dryer, ice skating, indoor pool, outdoor pool, game room, restaurant & bar, snack shop, gym & sauna & more!!! Please read all details below.

Sunset Bay Villa #202-Pool, Waterfront, Sunsets!

Located in the heart of historic downtown Chincoteague, this well appointed bayfront unit is just a few miles from Assateague Beach & The Chincoteague National Wildlife Refuge. Enjoy stunning sunsets over Chincoteague Bay from your private waterfront balcony. Lounge by the Bayfront pool (seasonal & unheated) or work out in the newly renovated gym. Walk to popular restaurants, shopping, town park, fishing pier, movie theatre & more.