
Condo rentals near Chesapeake Bay
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Top-rated condo rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness, and more.

Newly Renovated & Modern 1BR Condo - Unit 2
Completely renovated, stylishly furnished condo unit in Arlington, VA just one stoplight from Washington DC, the Pentagon, Clarendon, Crystal City and National Airport. Spacious unit with free cable TV, secure Internet/Wi-Fi, FREE RESERVED PARKING space in private lot, in-unit Washer/Dryer, Full Kitchen. Steps away from public transit buses that route to multiple Orange/Blue/Silver line Metro train. Comfortably accommodates the traveling professional, those on vacation and is kid friendly.
4.86 out of 5 average rating, 294 reviews
The Grand Delphey: Downtown Artist Retreat
Enjoy this stylish condo located in the heart of downtown's Historic District. The condo resides within a beautiful mansion known as the The Grand Delphey with shared rooms on the first level perfect for photo sessions or gathering. The unit has the ability to rent with 3 other units to SLEEP UP TO 16 PEOPLE! Please let us know if you would like to book the entire mansion for wedding parties or other events. Just steps away from wedding venues, Baker Park, the creek, downtown nightlife & shops!
4.96 out of 5 average rating, 186 reviews
Luxury Riverfront Condo w/ sunrise & sunset views
Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.
4.93 out of 5 average rating, 152 reviews
A bit of Paradise
Charming end unit secluded in the heart of Lewes. Shady sitting area for viewing the waterfowl & enjoying the peace & quiet. Lewes marina is across the street so is Quest where can rent Kayaks etc. Over the bridge you will enjoy the historic district, town shops, eateries, food market; kiddy park, canal front park; trolley into Rehoboth Beach Henlopen State Park 1 mile; surfing, fishing & nature trails; Bay Beach 1/4 mile w Walk to everything We offer a %15 discount for 7 days or more
4.87 out of 5 average rating, 346 reviews
The Bird's Nest in Historic Occoquan (Mins to DC)
Spacious condo in the heart of walkable historic Town of Occoquan. Second floor loft with full kitchen, bath, a comfortable queen bed, work station, w/d in unit & one free parking spot. The Town of Occoquan offers unique experiences (kayaking, fishing, birdwatching and shopping) all within walking distance. Excellent dining choices from award winning restaurants to casual eateries. Mins to I-95, 123, VRE. D.C. (35min); Quantico (25min); Potomac Mills (10min). Tysons (25min).
4.91 out of 5 average rating, 869 reviews
Annapolis @Gate 1 steps to the Harbor Free parking
Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1st floor 2 bed / 1 ba condo has been fully renovated with new paint, floors, bath & kitchen. 1 Parking space included & additional paid parking on street. Queen Bed & sleeper couch is a full size. Linens included. Kitchen includes refrigerator, stove/oven, microwave, keurig, dishes silverware, pots and pans. High speed internet included & separate work area.
4.91 out of 5 average rating, 153 reviews
Funky Uptown Apt meets Downtown - Hist District
Location location location where Uptown meets Downtown in the Historic District. 1/2 block to Dinner Under The ✨ , First Sunday Arts. Tsu, 49 West, Level in the front yard Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Eastport) is walking distance from this unique 2nd floor unit w elevated deck for morning coffee as Jazz wafts in, full kitchen, w/d, clawfoot shower/tub, MBR with Queen.
4.96 out of 5 average rating, 127 reviews
1st Floor Condo in Annapolis
This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock (limited access) and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.
4.96 out of 5 average rating, 180 reviews
The Loft 2B/2BA minutes to Rehoboth & Lewes Beach
Escape to a stylish coastal 2 bedroom 2 bath condo designed for relaxing beach vacations, family trips, and weekend getaways. Conveniently located just minutes from Rehoboth Beach and Lewes, The Loft offers the perfect combination of comfort, convenience, and coastal charm. Whether you're planning a family beach trip, a couples retreat, shopping weekend, or exploring Delaware’s beautiful coastline, you'll have everything you need for a memorable stay.
5.0 out of 5 average rating, 127 reviews
Cozy Old Town Apartment
Welcome to our charming condo in the heart of historic Old Town Alexandria! Enjoy a fully equipped kitchen, cozy living room with a 55” smart TV, and a peaceful master bedroom with en-suite bathroom. With two private entrances, dedicated parking, and easy access to King Street’s dining, shopping, and metro, this home offers comfort and convenience. Perfect for relaxing after exploring D.C., or enjoying the charm of Old Town on foot!
4.98 out of 5 average rating, 150 reviews
CANAL FRONT Wi-Fi, Roku, Netflix, boatslip, pool
BEAUTIFUL WATER VIEW ON 28 STREET. 1 bedroom apartment with full kitchen and bath. Bedroom has 2 full size beds, boat slip ,1 onsite parking spot included, plenty of parking available in front of building. Public transportation close by. Walk to beach,boardwalk, restaurants, miniature golf, go cart tracks, Jolly Rogers Amusement and Water park. Free WiFi, and Roku to connect to your streaming services. Coded entrance. Beach gear.
4.89 out of 5 average rating, 367 reviews
Bayside Retreat in the Heart of Ocean City!
Newly renovated condo!! -Water view. Watch the boat traffic. -Oversized balcony with comfortable seating. -Comfy LoveSac couch. -Walk to boardwalk or beach - 15 minutes. -Walk to Jolly Roger amusement park. -Fish off community dock down below unit. -Close to dining and shopping. -Kitchenette for cooking meals. -Fast Wifi and Streaming TVs. -Fully Stocked Home. Clean linens, towels, toilet paper, paper towels & more!
4.88 out of 5 average rating, 282 reviewsPopular amenities for condo rentals near Chesapeake Bay
Weekly condo rentals

Beach Sunrise: Walk to Downtown & Lewes Beach
4.98 out of 5 average rating, 370 reviews
Renovated Apt In Historic Dist w/2 Parking Spots
4.94 out of 5 average rating, 454 reviews
Newly renovated 1 bedroom apartment w/full kitchen
4.83 out of 5 average rating, 171 reviews
Sixteen West - Modern Apartment in Richmond
4.91 out of 5 average rating, 336 reviews
Coastal Modern Condo • Balcony, 2 Baths, East Rt 1
4.99 out of 5 average rating, 121 reviews
Modern & Cozy Retreat | Pool | Close to Beaches
4.95 out of 5 average rating, 327 reviews
Renovated Condo Near Outlets, 3.5 Miles to Beach
4.98 out of 5 average rating, 226 reviews
The Hideaway By The Bay OCMD
4.98 out of 5 average rating, 163 reviewsPet-friendly condo rentals

Hill East BnB - Modern Style and Comfort 3BR/3BA
4.98 out of 5 average rating, 354 reviews
Sojourn in DuPont Circle: Modern Meets Historic
4.89 out of 5 average rating, 105 reviews
Cozy Getaway in the City (Gallaudet/Union Market )
4.86 out of 5 average rating, 183 reviews
Beautiful Upper Level 1BR in Downtown DC
4.81 out of 5 average rating, 232 reviews
New, Sunny, 2BR - Parking, Patio, Firepit
4.9 out of 5 average rating, 286 reviews
Modern Spacious DC Condo 3BD/3BA
4.97 out of 5 average rating, 126 reviews
Luxury Condo • In the heart of National Harbor
4.91 out of 5 average rating, 200 reviews
Lewes Beach Vibes
4.98 out of 5 average rating, 109 reviewsCondo rentals with a pool

Beautiful Updated Condo Waterfront, Pool, Sunsets
4.91 out of 5 average rating, 101 reviews
Oceanfront Studio: Boardwalk, Beach, & Pool Views
4.97 out of 5 average rating, 158 reviews
2BR Coastal Escape with Pool Near Rehoboth Beach
4.95 out of 5 average rating, 123 reviews
Oceanfront Gem VaB Studio Exceptional Views
4.89 out of 5 average rating, 277 reviews
Water view at Ocean Pines Yacht Club Condo
4.97 out of 5 average rating, 229 reviews
Condo 2 Bedroom Waterfront Lewes/Rehoboth DE
4.98 out of 5 average rating, 222 reviews
Captains Quarters | Waterfront & Pool
4.98 out of 5 average rating, 124 reviews
Right on Silver Lake walk to the beach and town!
4.91 out of 5 average rating, 183 reviewsPrivate condo rentals

The Loft at Lakeside
4.94 out of 5 average rating, 186 reviews
Gem in the Heart of the Fan #3!
4.95 out of 5 average rating, 435 reviews
THE ROYAL: Nostalgic Go-Go Theme Suite w/Fireplace
5.0 out of 5 average rating, 101 reviews
Anchors Away
4.85 out of 5 average rating, 110 reviews
Station House West: Upscale Condo in Cambridge, MD
4.92 out of 5 average rating, 39 reviews
The Solomons Sunrise Suite
5.0 out of 5 average rating, 77 reviews
Beach Haven Hideaway ~ stunning water views!
4.92 out of 5 average rating, 50 reviews
Bayfront Boardwalk Condo w/ Sunrise Views
4.93 out of 5 average rating, 57 reviewsQuick stats about condo rentals near Chesapeake Bay

Total vacation rentals
Explore 140 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at ﺩ.ﺇ 37 per night before taxes and fees

Verified guest reviews
Over 5,840 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
130 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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- Condo rentals United States
- Chincoteague Island
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- Old Dominion University
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