
Fitness-friendly holiday rentals near Chesapeake Bay
Find and book unique fitness-friendly accommodation on Airbnb
Top-rated fitness-friendly rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Kone Oasis- hot tub, pool, theater/game rm.
Have fun and relax at this stylish oasis! Packed w/ amenities. Huge Pool w/multiple cabanas, HOT TUB, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room and outdoor projector too, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Basement apt so there is some movement noise. Updated bath and an outdoor shower. 20 mins from Downtown DC & 6Flags.

Waterfront 4-BR home w/ hot tub & charging station
Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

New Year’s Day is Available
Stunningly manicured and spacious custom built colonial on 6 private acres. - Specializing in large multigenerational family vacations, business and church retreats, and discerning private getaways. Perfect for those desiring comfort, style and space. - Massive covered deck with fire table and outside dinning. Start your day here with coffee and finish it with your favorite wine. -Collect fresh eggs and let the kids run!!! -17 min. to top Williamsburg attractions. -10 min. to outlet mall ;)

Ultra Modern Ground Floor Apartment
This unique place has a modern style all its own. It’s just been fully renovated and everything is new, from the floors to the appliances to the TV. On a quiet street only 5 minutes’ walk to the Metro, 2 minutes walk to the bus downtown. Walk to supermarkets, restaurants, deli, bakery, pharmacy and stores. 3 minutes walk to a National Forest with your furry friend! Off-street parking and EV charger. Lots of closet space and storage. Washer and Dryer. Your oasis in the city awaits.

Historic Manor - Main House
Nestled near the Chesapeake Bay and located just under an hour outside DC, it's the perfect getaway spot for time in nature making memories with family and friends. The Manor sits on almost 3 acres making it feel secluded and private while being close to the attractions, beaches and restaurants of the area. *The Manor has additional units on the property. Each unit is separate with private entrance. No indoor space is shared. Only the exterior property grounds are shared by other guests.

Chickahominy Riverside Guest Home By Williamsburg!
Our river-side guest house has everything you will need to enjoy your getaway! Enjoy the river, dock, 2 kayaks, paddle boards, 1 canoe, large game room, portable fire pit, playground, basketball goal and large outdoor sitting area with a gas grill. Located 5-20 mins from the finest wedding venues, nearby wineries; less than an hour to Richmond & 25 minutes to Colonial Williamsburg. Only steps to numerous historic plantations & a few miles from the Virginia Capital bike & walking trail.

Luxury Modern Home on Water+Hotub- Annapolis 25min
Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Welcome to our waterfront paradise overlooking the Chesapeake Bay! Experience comfort and tranquility at this extraordinary retreat, where breathtaking views and unforgettable memories await you. This serene beachfront property is little over an hour from DC & Northern Virginia, and about 90 minutes from Baltimore. With private pool, fire pit, kayaks, paddle boards, pingpong, weights & workout equipment, it's a perfect place to recharge and make memories with family and friends.

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.

5-BR Home near DC Metro -Free Parking/Full Kitchen
RARE FIND — Main-Level Bedroom & Bath with No Steps! Welcome to your stylish D.C. retreat! This fully renovated 5-bedroom, 4-bathroom home offers 3,500 sq ft of open-concept living, just 3 minutes from the Metro and 10 minutes from the White House. Enjoy free street parking. Perfect for families or business travelers with a main-floor bedroom, chef’s kitchen, double living rooms, fast Wi-Fi, and smart TVs. Book your stay today and experience D.C. in comfort and style.

Garage Parking <|> Xcape to Vibrant Old Town
You'll enjoy coming home to this beautiful and spacious Studio apartment in vibrant Old Town, Alexandria. With all its amenities, you'll automatically feel right at home. ❤ 2 Minutes from King Street. ❤ 5 Minutes from Reagan Airport. ❤ 7 Minutes from National Mall. ❤ 8 Minutes from MGM and National Harbor. Walk to restaurants and shopping near King Street. Great for professionals traveling to the area for work, couples or solo travelers. Perfect for longer stays!

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
Popular amenities for fitness-friendly rentals near Chesapeake Bay
Fitness-Friendly apartment accommodation

Luxury Oasis mins to DC|Free Parking|Metro|Family

#3 Foggy Bottom/Georgetown Apartment

King Size Bed - Reston Metro Apt

Capitol Hill 1BR, sleeps 4, Short Walk to Capitol

Amazon HQ-Luxurious DMV-WiFi-Cozy Suite-DC Airport

Navy Yard 1BR | Gym + Walk to Metro

Tysons View Fresh & Balcony

Deluxe 2BR Apt | Arlington | Gym, Pool
Fitness-friendly condo rentals

PENTHOUSE - 8TH Floor Boardwalk/Epic Views/Pool/

Luxury water-view condo with high-end finishes

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

2-Story Spa-Like Condo w/ parking, gym, steam room

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC

Love Above the Waves-Best Ocean View & Heated Pool

Ocean Escape

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom
Fitness-Friendly Holiday House

Peggy's Place - Historic Rowhome in the City

Waterfront Villa , 3 bedroom & theater/Game room

The Heights | Hotel Luxury w/ Garage | Near Metro

Large Home with Pool & 7 bedrooms; sleeps 21

Rally & Rest, Your Own Pickleball Awaits

Spacious 3-BR near DC, w/ Lotus Pond, Free Parking

Quiet Farm Stay near Annapolis

Where the Bay meets the Sky
Other fitness-friendly holiday rentals

The Ladybug - arcade, dog-friendly, firepit, & EV

Beautiful Waterfront Escape w/ Gorgeous Views

Farm Studio w/Bath+Kitchen+Laundry. Home Gym+SAUNA

Kayak friendly home on Chesapeake with golf cart

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

Modern 4-Story Townhome Retreat Minutes From DC

Modern Luxury in the Heart of McLean

Magnolia Cove waterfront 1BR upper cottage
Quick stats about holiday rentals that are fitness-friendly near Chesapeake Bay

Total holiday rentals
Explore 720 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 21,960 verified reviews to help you choose

Family-friendly holiday rentals
430 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 310 rentals that welcome pets

Holiday rentals with a pool
250 properties feature pools

Rentals with dedicated workspaces
500 properties have a dedicated workspace

Wi-Fi availability
720 of Chesapeake Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chesapeake Bay rentals

4.8 Average rating
Chesapeake Bay stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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