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

3FL 1Block 2 Water wParking,85tv,Fireplace,1 K bed
RowEnd Family Friendly w Parking The Perfect blend of urban charm & waterfront relaxation ideal for both leisure & business. Master BR original brick interior Q bed, work area. 2 BR pull-out K daybed, fireplace, 85" Tv, pullout couch. Bodyspray shower, wash+dryer combo.WiFi, Smart Tvs. Step outside find yourself immersed in vibrant Fells Point energy, known for cobblestone streets, historic architecture local boutiques, lively bars & restaurants, everything is walking distance 1 block from water

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.

3BR Luxury Retreat, Pond, Gym, Near DC
Wake up to birdsong beside a waterfall and lotus pond, just 20 minutes from downtown DC in peaceful Takoma Park. Our spacious 3-BR, 2.5-BA luxury retreat combines nature with urban accessibility - a sanctuary for both relaxation and adventure. Off-street parking, home gym, steam shower, EV charger, & five decks. Walk to organic market, restaurants, & scenic trails. Recent whole-house renovation. Our reviews say it all!! Superhost service to top it off. Montgomery County Reg # STR24-0017

Beach Access, Hot Tub, Pet Friendly, Fully Fenced
A serene escape awaits you at our cozy hot tub 4-bedroom retreat, minutes away from Historic Downtown Annapolis. As the sun sets, the deck comes alive under the soft glow of string lights beckoning you to unwind in our 8-person Bullfrog hot tub or outdoor firepit where your worries will melt away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Annapolis has to offer!

Chickahominy Riverside Guest Home By Williamsburg!
Our river-side guest house has everything you will need to enjoy your getaway! Enjoy the river, dock, two kayaks, paddle board, 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.

Peggy's Place - Historic Rowhome in the City
Located on picturesque Tyson St, Peggy's place is an historic rowhome in the heart of Baltimore's cultural district. Everything is here in this cozy home away- with a full amenity kitchen, office/workout room with printer and stationary bike and a 3rd floor balcony. Upper floors have one full bath each, with tub on the 2nd floor. Both rooms- 2nd floor full, 3rd floor queen - have a dresser and closet. Steps from major destinations - cultural, medical and transit. You'll love it here!

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

Kone Oasis- hot tub, pool, theater/game rm.
Have fun and relax! Near every amenity. Huge Pool w/multiple cabanas, hot tub, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room, 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. Now offering RV for additional cost to add additonal sleeping space. Basement apt so there is some movement noise. 20 mins to DC & National Harbor

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.

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

Flohom 1 | Floating Suite • 360° Skyline Views
FLOHOM 1 | Bay Escape is a coastal-eclectic floating suite with 360° skyline views, a rooftop fire pit, and a designer interior for four. Queen Helix Luxe bed with Parachute linens, fully equipped kitchen, and spa-like bath. The rooftop features a dining table, a sectional sofa, and lounge chairs overlooking the Inner Harbor. Includes parking at the marina and a short walk to Federal Hill, Camden Yards, and the water taxi. Welcome aboard. ✨
Popular amenities for fitness-friendly rentals near Chesapeake Bay
Fitness-friendly apartment rentals

Ultra Modern Ground Floor Apartment

Penthouse 2BR • Pool • Metro

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

Charming 1BR Apt | 5 Min to DC | Gym

Luxurious Retreat Prime Location

Liz Apartments European Starling Unit 408

Steps from U st. | 9:30 Club | Howard | Shaw

River View Suite - The Wharf DC
Fitness-friendly condo rentals

Sunset Bay Beach Condo

Elegant Condo with a Spacious Porch

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC

Spacious Bayside 2 BR Condo at Sunset Bay

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

21st Floor Carousel - 2 BR Oceanfront & Bay View

Love Above the Waves-OceanView/Rooftop Heated Pool

Direct Oceanfront with a View and Amenities Galore
Fitness-friendly house rentals

Come enjoy Summer on Smith Island at the HH Ranch

Modern 6BR • Close to DC & Annapolis

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Glebe Getaway House

Historic Manor - Main House

Brighton Winter House - Restored Historic Home

Wonderful beachfront house

Alice’s DelRay Cottage-Elegant/EV enabled Retreat
Other fitness-friendly vacation rentals

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

Beautiful Waterfront Escape w/ Gorgeous Views

Rare, Unique modern 5 minutes from MGM and Harbor

Magnolia Cove waterfront 1BR upper cottage

5BD Country Escape | Gym, Spa, Pool, & Fire Pit

Luxury, Modern 2-Bedroom Water Front Apartment!

Waterfront Retreat | Dock, Views, Near Annapolis

Luxurious Bay Front Condo
Quick stats about vacation rentals that are fitness-friendly near Chesapeake Bay

Total vacation rentals
Explore 730 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at G$6,274 GYD per night before taxes and fees

Verified guest reviews
Over 23,030 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 300 rentals that welcome pets

Vacation rentals with a pool
240 properties feature pools

Rentals with dedicated workspaces
520 properties have a dedicated workspace

Wi-Fi availability
730 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!
Destinations to explore
- Beach house rentals Chesapeake Bay
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- Fitness-friendly rentals United States
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