Fitness-friendly vacation rentals in Chincoteague

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.

Bayside & Beyond - Waterfront, Sunsets, Pool

Just a few miles from Assateague Beach & the Chincoteague National Wildlife Refuge Bayside & Beyond (Sunset Bay Villa #105) is a well appointed 1st floor Waterfront Condo w/ Boat Slip, Pool (Seasonal) & Gym Located in the heart of historic downtown Chincoteague Bayside & Beyond is walking distance to restaurants, shopping, town park, fishing pier & carnival grounds. Enjoy beautiful sunsets, fishing, crabbing & kayaking from just outside your door! Relax & soak in the sunshine by the shared pool!

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-OceanView/Rooftop Heated Pool

🥂 Complimentary bottle of champagne on arrival, endless ocean views, private balcony, golden sunrises, rooftop heated pool, and direct beach access set the stage for a dream vacation. Celebrate your love from the 15th floor of Love Above the Waves - a romantic heaven for birthdays, anniversaries, engagements, and special escapes for two. Inside, the open layout allows the Atlantic to become the centerpiece of your stay, whether you're relaxing indoors or stepping out onto the balcony.

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.

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 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

Stunning Oceanfront Unit in Amenity Rich Building

This condo is on the 18th floor of the Carousel and the views cannot be beat! There are two private balconies, a beautiful fully renovated 2 bed, 2 bath unit that comfortably sleeps 6 adults, but can fit up to 4 adults and 4 children.There is a $50CASH-ONLY non-refundable charge for parking, Carousel's amenities, and condo access card that is paid in person to the business office at the Carousel. This unit sells out quickly, book today!

Relaxing Retreat on the Hudson

Come escape to my 5-bed, 2-bath home on Hudson Creek! Featuring a deep pier with great crabbing, fishing, and boating, plus a bubbling hot tub and modern amenities throughout. Perfect for large groups, it comfortably hosts 15! Explore with complimentary kayaks, stay productive with WFH setups in every bedroom, and use my EV charger. Create unforgettable memories by the water.

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.

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.