
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!

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.

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 :)

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..

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.

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.

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.

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.

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
Weekly apartment rentals

One Bedroom Beachfront Apartment Mid-Town

Comfy 1BR w pond view Kingsmill

Ahoy Condo! Great ocean view just steps to beach!

Your Hideaway awaits/1-bedroom downtown pad.

Luxury Riverfront Condo w/ sunrise & sunset views

Direct Oceanfront close to Northside Park!

The Hideaway By The Bay OCMD

Direct Oceanfront with a View and Amenities Galore
Pet-friendly apartment rentals

Lovely Condo Steps 2Beach+Pool Unlimited Parking

Beachfront Getaway, Pet Friendly, Mermaid Suite

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

Where the Locals Live!!

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

Elegant Condo with a Spacious Porch

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

Chic's Beach Rental and Fishing
Apartment rentals with a pool

Stress-Free Family Beach Stay | Pool + Kid Perks

Cozy Condo on Silver Lake - Walk to the beach!

Salt Air Retreat - Rehoboth Beach

Love Above the Waves-OceanView/Rooftop Heated Pool

Ocean Pines Yacht Club Getaway Waterview

Beach condo w/pool! All linens & beach supplies

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
Private apartment rentals

Cozy beach side condo

Walk to Beach Relaxing Ocean City Apartment

Oceanfront•Sunrise Views•Pool•Private Balcony

Steps to Ocean! Beach Accessories. Uncrowded Beach

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

Downtown Condo, Parking, Walk to Beach & Boardwalk

The Solomons Sunrise Suite

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
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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- Apartment rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
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- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
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