Fitness-friendly holiday rentals in Assateague Island

Luxe Farm Retreat! Sleeps17-GameRoom-Gym-FirePit

Escape to Brooklyn Meadows – The Manor, a luxury 6-bedroom retreat on a 40-acre equestrian estate. This home is perfect for family reunions, group getaways, or corporate retreats, featuring a private pool, game room, fire pit, and gym — all surrounded by rolling horse pastures and peaceful country views. 🛍️ 10 min to downtown Berlin – “America’s Coolest Small Town” 🌊 10 min to Ocean City beaches 🐴 15 min to Assateague Island & its wild horses Experience the best of Maryland’s Eastern Shore.

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

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.

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Launch your fabulous beach getaway at amenity-rich Sunset Cove at Sea Watch, part of an oceanfront condo complex offering 3 pools, complimentary movie theater, game room, gym, and much more. Enjoy spectacular ocean and bay views from 2 balconies, smart TVs in every bedroom and living room with provided satellite programming, fully equipped kitchen, comfortable living and bedroom spaces–and that’s just the beginning as your group has a blast at the beach and all of Ocean City’s fun attractions.

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!

Reel Nauti - Luxury Stay

Welcome to beautiful Ocean Village in Ocean City - a Vacation Paradise! These gorgeous condominiums sit directly on a lake with stunning views of the fountains. Lounge by the lakefront Pool and watch Herons and Egrets frolic over the water. Villa #4 - fondly known as ‘Reel Nauti’ offers the Luxury you want, the Amenities you need, all at a family-friendly price. Perfectly situated for access to all the area has to offer, without the high prices, noise, and crowding of the direct beach stays.

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!

Amazing Bayside Views @Sunset309

Incredible Bayside sunset views in this 4 person, 1 bedroom, 1 bath beautifully decorated unit at the Coconut Malorie! NEWLY REMODELED FOR 2023! This fun and well-appointed condo features: - Private bedroom with queen bed, newly remodeled large kitchenette with everything you need to serve family and friends, 65-inch smart TV's, beach chairs, beach umbrella, large tile bathroom with shower and jetted spa tub, rainfall shower head, hair dryer, and large vanity mirror and outdoor pool!

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.

Nice 2 BR Oceanfront, Year Round Fun & Amenities!

Gorgeous kitchen & main areas renovated March ‘22. 2 bedroom, 1.5 bath, direct oceanfront condo on 7th floor of Golden Sands building in OC. It’s clean, comfy, stylish, full of amenities & in a great location. Great WiFi, 3 TVs with cable, DVD, well stocked kitchen & stunning ocean view with large balcony. Top floor has indoor pool, fitness room, sauna & game room. Outdoor pool, tiki bar, gift shop, market & deli open weather permitting in May, then daily by Memorial Day.

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