
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.

Come enjoy Summer on Smith Island at the HH Ranch
Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Updated enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. New front deck. Large bathroom with dual rainhead shower. Easy access to the water. Bikes and SUP available in the shed. Kayaks are covered outside by shed. Island is only accessible by boat. Enjoy the tranquility of this unique place.

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.

Hot Tub | Mini Golf | Arcade | Gym — Coastal Quad
Welcome to The Coastal Quad, New Jersey’s first pocket resort! You will be booking a stay in one of four luxurious, 1BR tiny cottage suites, so each visit is a new adventure! You will enjoy your own private hot tub, fire pit, grill, fenced-in yard, and access to a shared rooftop mini golf course, retro arcade, full gym with sauna, office, laundry facility and more. Located just steps from a quiet bay beach and a short drive to Cape May and Wildwood, this is the most exciting resort at the shore!

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.

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

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!

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

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.

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 rentals

River View Suite - The Wharf DC

Kone Oasis- hot tub, pool, theater/game rm.

Ultra Modern Ground Floor Apartment

Cozy | 1BR Apartment

Charming 1BR Apt | 5 Min to DC | Gym

#2 Foggy Bottom/Georgetown Apartment

Home Sweet Home Apartment in a beautiful home

Studio Tower
Fitness-friendly condo rentals

Luxury water-view condo with high-end finishes

OceanfrontStudio-Slps4-Pool-Pickleball-HBOMax-Dis+

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Elegant Condo with a Spacious Porch

Ocean & Bay Views - Newly Renovated! Local Family!

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Love Above the Waves-OceanView/Rooftop Heated Pool

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

Modern 6BR • Close to DC & Annapolis

Sauna, hot tub, great outdoor space!

New LUX home close to DC+metro

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

Beautiful, rustic/unique home near Gettysburg!

All 4 One | Beach Living

Rally & Rest, Your Own Pickleball Awaits

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

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

Spacious Townhome Near DC | Garage & Workspace

Rare, Unique modern 5 minutes from MGM and Harbor

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Historic Manor - Main House

Boats Welcome | Waterfront | Pool | Kayaks

Luxury, Modern 2-Bedroom Water Front Apartment!

Quiet Farm Stay near Annapolis
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$6,279 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
- Rentals with outdoor seating Chesapeake Bay
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- Fitness-friendly rentals United States
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- Chrysler Museum of Art
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