Apartment rentals near Chesapeake Bay

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Top-rated apartment rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Apartment in Ocean City
4.93 out of 5 average rating, 150 reviews

Oceanfront 1Bedroom/1.5 Bath Condo-Slps 4-King Bed

Serenity Now – Oceanfront Condo in North Ocean City | Walk to Dining & Northside Park Wake up to ocean views at Serenity Now, your cozy beachfront condo in North Ocean City, MD! This updated 1-bedroom unit sleeps 4 with a king bed and a queen sleeper sofa, plus it features a fully equipped kitchen, electric fireplace, 1.5 bathrooms, and flat-screen TVs for relaxing nights in. You're just steps from the beach and a short walk to local favorites like Crab Bag, Tequila Mockingbird, and Sushi Cafe.

Top guest favourite
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.
Apartment in Ocean City
4.99 out of 5 average rating, 132 reviews

Gorgeous Beachfront! King Bed, Direct Ocean 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 favourite
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.
Apartment in Frederick
4.99 out of 5 average rating, 170 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!

Guest favourite
A bright living area features large windows that overlook the ocean, with comfortable seating arrangements. A small dining table for four is paired with white chairs. Light-colored walls create an airy feel, while a colorful bookshelf adds a pop of interest to the space.
Apartment in Ocean City
4.96 out of 5 average rating, 218 reviews

Luxury Oceanfront Escape!

This unique place has a style of its own. Wake up, pour your cup of coffee, and watch the sunrise from your direct oceanfront balcony. The beach is a few short steps away. Walking distance to many restaurants and shops! This recently renovated one bedroom condo features an outdoor shower, an elevator, fully equipped kitchen, a library of books, 1.5 bathrooms, Wi-Fi, large screen smart tv, bedroom tv, parking spot, washer/dryer and so much more! Fresh linens, towels, and toiletries included.

Top guest favourite
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.
Apartment in Ocean City
4.92 out of 5 average rating, 885 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 favourite
White Adirondack chairs are positioned along a lakeside path, offering a view of calm waters surrounded by vibrant autumn foliage. The ground is covered with fallen leaves, and a large tree casts gentle shade nearby.
Apartment in Rehoboth Beach
4.9 out of 5 average rating, 101 reviews

1 Bedroom 1 Bath Condo on Silver Lake

Newbold Square is tucked away in Rehoboth Beach on Silver Lake. It is a quiet, sleepy, 40 unit complex with a lakeside pool that offers sun and shade among towering trees. This condo has one bedroom and one bathroom. There is also a queen size sleeper sofa. There is a well stocked kitchen with plenty of storage space. We supply linens, bath towels, four beach towels, four beach chairs, a beach wagon, and a gas grill. No pets are permitted. Our space is allergen free.

Top guest favourite
Apartment in Ocean City
4.96 out of 5 average rating, 311 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

Top guest favourite
Apartment in Ocean City
4.99 out of 5 average rating, 322 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.

Top guest favourite
The rooftop pool features vibrant blue water, surrounded by a spacious deck. Lounge chairs are positioned alongside the pool, providing a relaxing view of the marina and distant town structures. Clear blue skies enhance the serene ambiance of this outdoor space.
Apartment in Annapolis
4.96 out of 5 average rating, 145 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.

Top guest favourite
A spacious living area features two large sofas, one being a queen sleeper bed. A wooden coffee table sits on a neutral area rug. A dresser and smart TV are positioned along the wall, with a dining area visible through an open layout.
Apartment in Rehoboth Beach
5 out of 5 average rating, 104 reviews

Stylish Coastal Loft Minutes to Rehoboth & Lewes

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.

Top guest favourite
Apartment in Ocean City
4.91 out of 5 average rating, 140 reviews

Cozy Beach Front Condo with Modern Amenities.

Our condo is located on a quiet street, just steps away from the oceanfront. The perfect beach getaway at our cozy condo, situated across the street from Seacrets, mini, restaurant, an array of entertainment options. Accommodates up to 4 guests, features well-stocked kitchen, 2 smart TVs for streaming, WiFi, A/C, washer/dryer, dishwasher, microwave, hair dryer, iron, kitchenware. Relax on the balcony, 1 designated parking space, outdoor shower after.

Top guest favourite
Apartment in Ocean City
4.99 out of 5 average rating, 104 reviews

Ocean block condo

Kick back and relax in this calm, newly remodeled condo only a few steps from the beautiful Ocean City beach. Located uptown , across the street from Starbucks, Juice Bar, Wawa, Justine's Ice Cream, CVS Pharmacy, McDonald's, Candy Kitchen and a lot of restaurants like Crabcake Factory and Tailchasers. Northside Park on 125th St is a quick walk to watch soccer tournaments or July fireworks. Park your car in the lot and take the OC bus for $4 all day.

Popular amenities for apartment rentals near Chesapeake Bay

Quick stats about apartment rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 140 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at €26 per night before taxes and fees

  • Verified guest reviews

    Over 5,600 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    130 of Chesapeake Bay holiday rentals include wifi 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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