
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.

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!!

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!

Barnyard Retreat
We are BACK After a 2 year hiatus!! We cannot wait to see all of our wonderful guests again! Beautiful 750 sq. ft. in-law apartment set up in a very efficient setting with open living space and Jack-n-Jill bathroom. Space is very open with cathedral ceilings and sky-lighting. Apartment has it's own separate entrance and dedicated parking space. The apartment has fast, secure wi-fi and is set-up perfectly for traveling professionals! Please see additional info within our house rules section.

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 :)

The Loft at Lakeside
Welcome to the The loft at Lakeside! The loft is a completely separate space that comes with its own entrance and parking space. The loft consists of a spacious bedroom with a walk-in closet. There is a full bathroom in the bedroom and a half bath near the kitchen. The main space consists of spacious Kitchen that sits right next to the cozy family room, with a large couch. It also has a full laundry room for anyone looking to take home clean clothes after an amazing stay at The Loft.

Beach Sunrise: Walk to Downtown & Lewes Beach
Skip the traffic and parking stress — stay where everything is steps away. Experience the best of Lewes (pronounced loo-iss) from this perfectly located, walkable condo. Step outside and you’re minutes from the beach, downtown dining, scenic parks, and bike trails. With ultra-fast 2-Gig Wi-Fi, KING bed, free bikes, coffee bar, easy parking, and thoughtful amenities, this is the ideal home base for couples or small families seeking comfort, convenience, and an authentic local stay.

The Hideaway By The Bay OCMD
Relax and enjoy your stay in this bright and welcoming waterfront, 1 bed, 1 bath condo. Bring your kayaks or paddle boards! This condo is located right off of 28th street, on the bay. It is a 14 minute walk to the beach and the Ocean City boardwalk, and within walking distance to many Ocean City attractions. All guests are provided with an electronic WELCOME BOOK prior to arrival which includes everything we think they will need to know about the condo and the surrounding area.

2 Bedroom Stylish Kingsmill condo
Located in the beautiful Kingsmill resort, this charming two bedrooms, two baths condo with stunning seasonal views over the pond is only a few minutes away from CW, Busch Gardens, water country, William and Maryand other Williamsburg attractions. All Kingsmill amenities are not included as they are strictly for Kingsmill residents Guests have access to the Spa and to the Mill Coffee House which is within walking distance from the condo and serves breakfast and lunch every day..

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.

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.

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.

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!
Popular amenities for apartment rentals near Chesapeake Bay
Weekly apartment rentals

Cozy beach side condo

Comfy 1BR w pond view Kingsmill

Lovely Ocean Block 1 BR near Convention Center!

Capts Qrtrs - Awesome downtown Annapolis location!

Your Hideaway awaits/1-bedroom downtown pad.

Chic's Beach Rental and Fishing

1st Floor Condo in Annapolis

Stylish Coastal Loft Minutes to Rehoboth & Lewes
Pet-friendly apartment rentals

Lovely Condo Steps 2Beach+Pool Unlimited Parking

Beachfront Getaway, Pet Friendly, Mermaid Suite

Renovated Apt In Historic Dist w/2 Parking Spots

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

Elegant Condo with a Spacious Porch

1st Floor 2BR/2BA | Pool | Quiet & Convenient

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

Hill East BnB - Modern Style and Comfort 3BR/3BA
Apartment rentals with a pool

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Salt Air Retreat - Rehoboth Beach

1 Bedroom 1 Bath Condo on Silver Lake

Renovated Condo Near Outlets, 3.5 Miles to Beach

Clean and Comfy, Close to Beach and Shopping

Love Above the Waves-OceanView/Rooftop Heated Pool

Beach condo w/pool! All linens & beach supplies

Sunrise Studio - Ocean Front, on Boardwalk, Pool!
Private apartment rentals

Ultra Luxe Oceanfront Escape w/Breathtaking Views!

La Pescadora - Cozy. Coastal. Completely Yours.

Oceanfront•Pool•Private Balcony w/Sunrise Views

Steps to Ocean! Beach Accessories. Uncrowded Beach

Downtown Condo, Parking, Walk to Beach & Boardwalk

The Solomons Sunrise Suite

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

Direct Oceanfront close to Northside Park!
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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