
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.

Magnolia Cove waterfront 1BR upper cottage
Welcome to Magnolia Cove cottage! Travel back in time along a magnolia-lined lane for a charming waterfront stay. On 11+ private acres, the guest upper cottage is separate from owner's 1937 manor home. Water surrounds the property on 3 sides. Enjoy kayaking in the Put-in-Creek and swim/fish right off your private dock. 6+ft deep water docking available for boat owners. Bike/drive minutes into the peaceful town of Mathews VA w/ galleries, shops and restaurants. Local beaches min away.

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!

Walkable 2 Orioles & Ravens Stadium
Experience the best of Baltimore from our Federal Hill location! You"ll be steps away from some of the city's top restaurants, bars, West Covington Park, M&T Bank Stadium, Camden Yard, and more! Take a stroll through the charming streets to the nearby Federal Hill Park for stunning views of the Inner Harbor. Enjoy easy access to major highways and public transportation, making it easy to explore all the city has to offer. You'll find something for everyone within walking distance of our space.

Kone Oasis- hot tub, pool, theater/game rm.
Have fun and relax at this stylish oasis! Near every amenity. 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 DC & National Harbor

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.

Garage Parking <|> A Cozy and Stylish Suite Xcape
King Bed! Garaged Parking! You'll enjoy coming home to this stylish 1-bedroom executive 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. ❤ 9 Minutes from Pentagon. Walk to restaurants and shopping near King Street. Great for Traveling Executives, Families, Couples, Solo Travelers or Traveling w/Friends. Perfect for longer stays!

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.

Modern 3-Level Stay| Hot Tub | Game Room | Parking
Spacious 5BR home near D.C. with hot tub, fire pit, and game room—perfect for families or groups! Enjoy 3 levels of comfort, a full kitchen, fast Wi-Fi, smart TV, and self check-in. Relax in the private backyard, grill out, or unwind in the hot tub. Pet-friendly and sleeps 12 comfortably. Located in a quiet neighborhood just minutes from downtown Silver Spring and Washington, D.C. Free parking, kid-friendly, and ideal for work trips or weekend getaways. Book your stay today!

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

Beach Home | King Bds | Firepit | Backyard Dining
Welcome to A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.
Popular amenities for fitness-friendly rentals near Chesapeake Bay
Fitness-Friendly apartment accommodation

Stylish1BR, FREE Parking, Pool,Gym,Wifi

Charming 1BR Apt | 5 Min to DC | Gym

Studio King Bed•Gym Near Boeing HQ/DC/Metro/Mall

Home Sweet Home Apartment in a beautiful home

Relaxing Stay Near Inner Harbor

#Cozy *King Suite* in the heart of #Towson

Furnished Corporate Apartment Near NAS Pax

#1 Foggy Bottom/Georgetown Apartment
Fitness-friendly condo rentals

Oceanfront Condo, Heated Pool, Fitness Center

Spacious Condo•Pond Views•Centrally located

*+Updated 5* Bayside 3BR Condo by Sun Ridge pool+*

Great value! Popular Powhatan Resort 2BDR

3 Bedroom Suite in Historic Williamsburg!

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC

Wyndham National Harbor | 1BR/1BA King Bed Suite

Colonial Williamsburg Spacious 4 Bedroom Suite!
Fitness-Friendly Holiday House

Family Retreat: 5BD/4B Games+ FP+BBQ+Arcade & more

Modern 6BR • Close to DC & Annapolis

Sauna, hot tub, great outdoor space!

Broadkill Beach Bliss: Coastal Charm, Wild Beauty!

Large Home with Private Pool, Gym, Sauna, 7 Bedroo

Alice’s DelRay Cottage-Elegant/EV enabled Retreat

Spacious 3-BR near DC • Lotus Pond • Free Parking

Marsh-Front Waterfront Retreat w/ Hot Tub
Other fitness-friendly holiday rentals

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

Beautiful Waterfront Escape w/ Gorgeous Views

Palisades Casita @ Sibley

Waterfront/Arcade/Fishing Fun

Historic Manor - Main House

Luxury, Modern 2-Bedroom Water Front Apartment!

Flohom 7 | 360° Harbor & Skyline Views

Relaxing Home w/ Sauna & Firepit, 20 Mins to D.C.
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 22,510 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
240 properties feature pools

Rentals with dedicated workspaces
510 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wifi 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
- Rentals with outdoor seating Chesapeake Bay
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- Fitness-friendly rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- Buckroe Beach
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Nauticus
- Town Point Park
- First Landing Beach
- Virginia Living History Museum
- Old Dominion University
- Hampton University
- Chrysler Hall
- Neptune's Park
- USS Wisconsin (BB-64)
- Children's Museum of Virginia




