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.

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Top guest favorite
A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.
Condo in Ocean City
4.99 out of 5 average rating, 118 reviews

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!!

Top guest favorite
A view of the outdoor deck and water can be seen through the open sliding glass door. Sunlight reflects off the calm water, creating a serene atmosphere. The steps lead to the dock, framed by white railings and a wooden deck.
Condo in Ocean City
4.91 out of 5 average rating, 229 reviews

**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

Top guest favorite
A stylish living area features hardwood flooring, a cozy gray couch, and a dark coffee table. Wall art and framed photographs adorn the walls, while large windows allow natural light to enter. A kitchen bar with stools is positioned alongside the living space.
Condo in Frederick
4.99 out of 5 average rating, 151 reviews

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!

Top guest favorite
Condo in Ocean City
4.98 out of 5 average rating, 113 reviews

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.

Top guest favorite
The living area displays a light-filled space with large sliding glass doors that open to an oceanfront balcony. A neutral-colored couch is accompanied by a round wooden dining table. A large mirror and minimalist decor enhance the room's serene atmosphere, with a view of the sea in the background.
Condo in Ocean City
4.92 out of 5 average rating, 863 reviews

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 :)

Top guest favorite
Condo in Annapolis
4.97 out of 5 average rating, 319 reviews

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

Guest favorite
A comfortable living area features a gray sofa with blue accent pillows and a textured rug. Large sliding glass doors offer a view of the ocean and access to a private balcony with outdoor seating. Natural light fills the space, creating a welcoming atmosphere.
Condo in Ocean City
4.98 out of 5 average rating, 244 reviews

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

Top guest favorite
A modern living area features a comfortable gray sofa positioned across from a coffee table. Large sliding glass doors offer ocean views, while light drapes frame the windows. A mirror reflects the space, and soft textiles add warmth to the atmosphere.
Condo in Ocean City
4.97 out of 5 average rating, 143 reviews

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

Guest favorite
The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.
Condo in Ocean City
4.94 out of 5 average rating, 312 reviews

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.

Top guest favorite
A modern living area is presented, featuring a plush gray sofa and a minimalist coffee table. A large television is mounted on the wall opposite the seating. Natural light filters through sliding glass doors, which lead to a private balcony with a small table and chairs.
Condo in Ocean City
4.99 out of 5 average rating, 308 reviews

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.

Superhost
A scenic view is captured through the window, showcasing a gazebo in a public square by the ocean. The serene ocean can be seen in the background, with gentle waves meeting the shore under a cloudy sky.
Condo in Rehoboth Beach
4.75 out of 5 average rating, 268 reviews

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)

Top guest favorite
A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.
Condo in Annapolis
4.96 out of 5 average rating, 124 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 and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

Popular amenities for condo rentals near Chesapeake Bay

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!

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