
Condo rentals near Chesapeake Bay
Find and book unique condos on Airbnb
Top-rated condo rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness, and more.

Gorgeous New Beachfront! King Bed, Direct Sea View
Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

**Beautiful newly renovated OC MD water view home*
Beautiful Bay view ground floor unit steps away from the water, 1 free parking spot available for guests and tons of street parking comfortable for 2 people for a long stay and 4 for a weekend getaway Located in the middle of all Ocean city major attractions Walking distance to the beach and Jolly Roger Amusement water Park and tons of other activities and restaurants. 6 min away from famous Seacrets, Macky’s & Fish Tales 8 min drive to OC famous board walk & downtown 15 min to Shopping Outlets

The Grand Delphey: Downtown Modern Penthouse
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 lounge 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!

Oceanside Retreat | Steps to the Beach
Welcome to 72nd Street, Oceanside — the perfect spot for your Ocean City family getaway! Located less than half a block from the beach, this beautifully maintained second-floor, 960 square foot condo offers comfort, convenience, and a prime midtown location. This part of town has fewer high-rises, meaning more beach space for your family to enjoy and less crowded than other streets. Every inch of this unit has been thoughtfully updated to provide a relaxing, well-appointed coastal retreat.

Light and Airy Oceanfront Condo with Large Porch
Wake up to the sound of the waves crashing outside your window and finish off your days relaxing on the private balcony as you watch the moon rise over the ocean. Come find your serenity by the sea in our modern oceanfront condo. Located in midtown Ocean City, you can keep your car parked in our dedicated spot and walk to many of the towns best restaurants, bars, and entertainment as well as the Convention Center and Performing Arts Center. Morning beach strolls and evening sips await :)

Annapolis Waterfront Condo - Unit #: A-203
Cozy, comfortable condo. Great views - 2nd flr. Fireplace 1 bed/bath condo, sleeps 4 max, covered, water front deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy stadium. Book NOW for the Summer! Easy access to Spring/Fall boatshows. 12 stairs, no elevator. Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another

Cozy oceanfront condo with stunning ocean views
Fully updated 1 bed/1 bath oceanfront condo in a quiet, mid-rise building with a beachfront pool in uptown OC. The perfect unit for a quick romantic getaway, long weekend, or family vacation. We are happy to accommodate the dates and timeframes that meet the needs of our guests. If possible, please consider these recommended timeframes for your booking: Memorial Day - Labor Day -7 Nights, Fri-Fri or Mon-Mon -3 Nights, Fri-Mon -4 Nights, Mon-Fri Labor Day - Memorial Day -Any 2 Nights

Cozy Direct Oceanfront!
Our beachfront 1-bed, 1.5-bath condo for four offers a spacious living area, fully equipped kitchen with a breakfast bar, and a luxurious bedroom with a king bed, all steps from the beach. Enjoy ocean views from the balcony, stay entertained with an HDTV and Roku, and explore nearby dining and entertainment, leaving your car in the designated parking spot. The condo, recently updated, provides versatile sleeping options, modern amenities, and convenient bathrooms for a comfortable stay

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.

Steps to the Beach, Ocean View 1BR, Renovated
Steps to the beach! Fully renovated, bright, modern, clean condo with a balcony view of the ocean. Quiet North Ocean City location with walking distance to restaurants, bus, 7-11, Mini golf course, movie theater, parks, etc. Brand new appliances and furniture. Free WiFi, King Size Bed, 60" & 40" TVs. Pull Out Queen Sofa, Brand New Full Bathroom. Washer and Dryer in the unit. Keurig Coffee Station, iPhone Charging station. Private balcony. Free Parking Space.

Rehoboth Ave Boardwalk, Ocean & Bandstand Views U2
You truly can not ask for a better location! Directly across from the bandstand, your beautifully renovated condo is STEPS from the boardwalk and beach. Enjoy Boardwalk and Ocean views in this modern & stylish 2 bedroom 1 bath condo with your private entrance located directly on Rehoboth Avenue (THE MAIN DRAG) steps from the boardwalk. Little to no street noise even with the windows open! (3 night minimum during high season ; 2 night minimum offseason)

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 and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.
Popular amenities for condo rentals near Chesapeake Bay
Weekly condo rentals

𝙂𝙪𝙚𝙨𝙩 𝙛𝙖𝙫𝙤𝙧𝙞𝙩𝙚 Lovely 2lvl Condo Steps 2Beach+Pool

Ocean Block | Sunchaser Condo | Surfer's Dream

Capts Qrtrs - Awesome downtown Annapolis location!

On the Bay, Private Beach-Boat Slip

☀️ Ocean block | Midtown OCMD

Perfect location!

Oceanside Charm, desirable midtown Ocean City, MD

Oasis by the Ocean - Direct Oceanfront
Pet-friendly condo rentals

Luxury water-view condo with high-end finishes

Walk to beach lovely 2/2 in "Kingsmill on James"

Read Ave Dewey Condo - Bay Front, Private Beach

Bethany Bay. Sleeps 4. AC, Pool, Ground Floor

Spacious Condo•Pond Views•Centrally located

Beautiful waterview 2B condo w/Dock&Close to Beach

Spacious| Modern & Cozy| Pool| Close to the Beach

Lux Direct Oceanfront*Deck*Pets welcome*Arcade*
Condo rentals with a pool

Oceanfront Family Oasis: Pool, Beach & Parking!

White Marlin 107 Renovated Amazing Bay Views Pool

Renovated Condo Near Outlets, 3.5 Miles to Beach

Beautiful 2BR 2BA oceanfront condo at the Atlantis

Comfy and Convenient 2 bedroom/2 bath condo

Love Above the Waves-Best Ocean View & Heated Pool

Direct Ocean Front/Gorgeous Views/Indoor Pool

First Floor Comfort and Convenience
Private condo rentals

Lovely Ocean Block 1 BR near Convention Center!

Walk to Beach Relaxing Ocean City Apartment

La Pescadora - Cozy. Coastal. Completely Yours.

Annapolis @Gate 1 steps to the Harbor Free parking

Ocean Block Boho Beach House

Condo in Downtown Rehoboth, with bikes

Beach Baby Ocean Block Studio-Mid Town-All U Need

Barnyard Retreat
Quick 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.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 5,680 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

4.9 Average rating
Chesapeake Bay stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- House rentals Chesapeake Bay
- RV rentals Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Resort rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Vacation home rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Rentals with a home theater Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washer and dryer Chesapeake Bay
- Condo rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- Buckroe Beach
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Town Point Park
- Nauticus
- First Landing Beach
- Virginia Living History Museum
- Old Dominion University
- Hampton University
- Chrysler Hall
- Neptune's Park
- USS Wisconsin (BB-64)
- Children's Museum of Virginia




