Fitness-friendly vacation rentals in Assateague Island

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf

Immediate removal of stress at the front door. Being nestled in a marina’s serene waterfront & nature park is good for the soul. Relax in a jetted tub after a sun filled day & an al fresco meal on a back porch with charming outdoor dining. An open concept main level features large windows & comfortable seating through the entire property. 2 full bathrooms upstairs & a king sized bed provide maximum comfort & outdoor living on 2 balconies. Additional fees for pools, pets, >3 guests may apply.

Sunset Bay Villa 315-Downtown, Pool, Gym, Sunsets!

Located just a few miles from Assateague Beach & the Chincoteague National Wildlife Refuge. Sunset Bay Villa #315 is walking distance to Historic Downtown Chincoteague, Restaurants, Shopping & Carnival Grounds. Open concept, kitchen, living room & dining room. Enjoy sunset views from the deck off the Living Room & Primary King bedroom. King bedroom features jetted tub & separate shower & double sink. Queen bedroom & pyramid bunk bedroom share hall bath. Great fitness room next to pool area!

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.

Stunning waterfront panoramic view getaway house

Welcome to this thoughtfully remodeled waterfront property on the beautiful eastern shore of Virginia. Immerse yourself in jaw-dropping panoramic canal views of the Chincoteague Bay. Secluded escape for the nature enthusiast, balanced with country club amenities. Pools, boating and a golf course are within walking distance. Outdoor adventures and pristine beaches are just a short drive away! This property was designed to gather, recharge, explore, love, work remotely and inspire.

Beachfront 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 a breathtaking 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.

Sunny Bayside Escape

Welcome to Sunny Bayside Escape, a stunning 3-bedroom, 2.5-bath townhome nestled in the peaceful Bayside community. This spacious retreat features multiple cozy living and dining areas, a large porch perfect for sipping coffee and listening to nature, and gorgeous water views. Enjoy community perks like indoor/outdoor pools, tennis courts, a fitness center, kayak launch, and more—just minutes from Assateague and Ocean City beaches, dining, and nightlife!

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!

‘Dockside Retreat’ -pool, minutes to OC/beaches

Escape to Dockside Retreat in Bayville Shores, a private community on the scenic Little Assawoman Bay. Start your mornings with beautiful views, unwind with community amenities, or head out for adventure. Splash at Thunder Lagoon, race at Viking Go-Karts, or shop and dine by the coast. Beaches are just minutes away—Fenwick Island (2.5 mi), State Line (2.7 mi), Bethany (4.5 mi), and Ocean City (6.1 mi). The perfect blend of relaxation and fun awaits!