
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.

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!

Deluxe Zen Pond Retreat, 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

The Williamsburg Retreat- Gorgeous Private Acreage
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 ;)

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!

Waterfront | Swim Spa + Sauna + Beach + Game Room
Escape to Oyster Bay Getaway, a stunning 4-bedroom waterfront retreat designed for relaxation and fun. Enjoy serene water views throughout the home, unwind in the swim spa or sauna, and cozy up by the indoor fireplace. Step outside to a private dock and fire pit perfect for evenings under the stars. The garage game room (unconditioned) and indoor lounge with poker table make this the ideal getaway for families and groups seeking comfort, entertainment, and a true waterfront experience.

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.

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

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!

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

DC View•Balcony•Gym•Garage Near DC/Metro/Mall

#3 Foggy Bottom/Georgetown Apartment

Upscale 1Bdrm Apt in Heart of DC

Ultra Modern Ground Floor Apartment

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

Charming 1BR Apt | 5 Min to DC | Gym

River View Suite - The Wharf DC

Furnished Corporate Apartment Near NAS Pax
Fitness-friendly condo rentals

Direct Oceanfront with a View and Amenities Galore

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

21st Floor Carousel - 2 BR Oceanfront & Bay View

2BRCapri: Indoor Pool, Game Room, Massage Chair

Luxury Condo • In the heart of National Harbor

Love Above the Waves-OceanView/Rooftop Heated Pool

Direct Ocean Front 1BR Condo indoor/outdoor pools

Elegant Condo with a Spacious Porch
Fitness-Friendly Holiday House

Peggy's Place - Historic Rowhome in the City

Rally & Rest: Pickleball & Designer Home

Modern 6BR • Close to DC & Annapolis

Alice’s DelRay Cottage-Elegant/EV enabled Retreat

New LUX home close to DC+metro

Entire Guest Suite/Apt in Silver Spring/FDA/NSA

Come enjoy Summer on Smith Island at the HH Ranch

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Other fitness-friendly holiday rentals

Luxury, Modern 2-Bedroom Water Front Apartment!

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

Bring your Boat! | Waterfront | Pool Open 5/1-10/1

Rare, Unique modern 5 minutes from MGM and Harbor

Brighton Winter House - Restored Historic Home

Private Pool + Spa Retreat | Maryland Crab Feasts

Historic Victorian Walkability Chesapeake City

4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre
Quick stats about holiday rentals that are fitness-friendly near Chesapeake Bay

Total holiday rentals
Explore 760 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $34 NZD per night before taxes and fees

Verified guest reviews
Over 24,050 verified reviews to help you choose

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

Pet-friendly accommodation
Find 370 rentals that welcome pets

Holiday rentals with a pool
280 properties feature pools

Rentals with dedicated workspaces
570 properties have a dedicated workspace

Wi-Fi availability
760 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
- Beach house rentals Chesapeake Bay
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- Fitness-friendly rentals United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- First Landing Beach
- Neptune's Park
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Nauticus
- Town Point Park
- Virginia Living History Museum
- Mount Trashmore Park
- USS Wisconsin (BB-64)
- Chrysler Hall
- Sandy Bottom Nature Park
- The NorVa
- Willoughby Beach
- Hampton Coliseum





