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

Love Above the Waves-Best Ocean View & Heated Pool
🥂 Complimentary champagne on arrival, endless ocean views, private balcony, breathtaking sunrises, swimming pool and beach strolls await you at this romantic retreat. From the 15th-floor balcony Love Above the Waves offers sweeping Atlantic views and the perfect setting for birthdays, anniversaries, engagements, or quiet escapes for two. Let the ocean be your witness, the champagne your spark, and the sunrise your reminder that some moments are meant to stay with you forever above the waves.

Alice’s DelRay Cottage-Elegant/EV enabled Retreat
This is a beautiful 1938 cottage with gardens on all 4 sides of the property for drinks w/ Friends or grilling with Family. There are multiple skylight sources of natural light. The office space will support any collaboration requirement. Relax in the gardens while your car is plugged into the ChargePoint EV Charger. This is a very comfortable house for any season or length of stay. The house, patios and gardens make an excellent gathering spot for friends and associates to reconnect and relax.

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

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

Spacious 3-BR near DC • Lotus Pond • Free Parking
Wake up to birdsong beside a waterfall & tranquil lotus pond, just 20 min to downtown DC. Spacious 3-bed retreat offers on-site parking, super fast WIFI, home gym, steam shower, yoga space, EV charger, & five decks. Walk to organic market, restaurants, & scenic trails in peaceful Takoma Park. Recently renovated from top to bottom. Plan your adventures by day/relax by the pond at night. Our reviews say it all!! Superhost service to top it off. Montgomery County Reg # STR24-0017

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!

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

Ultra Modern Ground Floor Apartment

King Bed <|> A Stylish Executive Suite Xcape

#3 Foggy Bottom/Georgetown Apartment

Sea Colony Beach And Tennis Resort

Westgate Historic Williamsburg One Bedroom

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

Home Sweet Home Apartment in a beautiful home

Rehoboth Beach 2BR/2BATH Condo
Fitness-friendly condo rentals

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

Spacious Condo•Pond Views•Centrally located

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Ocean & Bay Views - Local Family Owned & Operated

Luxury at the Beach.

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Direct Ocean Front/Gorgeous Views/Indoor Pool
Fitness-friendly house rentals

Modern 6BR • Close to DC & Annapolis

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

More Luxury = Gym + Entertainment + Best Location

Historic Manor - Main House

Oasis Retreat Hot Tub, Pet Friendly, Fully Fenced

Marsh-Front Waterfront Retreat w/ Hot Tub

Relaxing Retreat on the Hudson

The Williamsburg Retreat- Gorgeous Private Acreage
Other fitness-friendly vacation rentals

Ocean Pines 2BR 1BA Cottage with Fire Pit

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

Beautiful Waterfront Escape w/ Gorgeous Views

Get away to the Chesapeake Bay at the HH Ranch

Family + Pet-Friendly Home Near Fenwick Island

Broadkill Beach Bliss: Coastal Charm, Wild Beauty!

Magnolia Cove waterfront 1BR upper cottage

Luxury, Modern 2-Bedroom Water Front Apartment!
Quick stats about vacation rentals that are fitness-friendly near Chesapeake Bay

Total vacation rentals
Explore 720 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 22,510 verified reviews to help you choose

Family-friendly vacation rentals
430 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 310 rentals that welcome pets

Vacation 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 vacation 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!
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- Fitness-friendly rentals United States
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