
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 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!!

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.

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

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.

Short walk to Beach & Boardwalk | 2BR/2BA Condo
Here's why you'll love it here: 🌊 Perfect Location: 5-minute walk to the beach & Boardwalk. 🛌 Comfort: 2 Full Bathrooms & Smart TVs in every room. 🌅 Sunset Views: A quick 1 minute walk to the bay for beautiful sunsets 🚗 Easy Parking: 2 dedicated spots (rare in OCMD!). 1st Floor modern 2BR/2BA Ocean City condo. Located perfectly between the ocean & bay, just a short walk to the Boardwalk and beach. Sleeps 6 comfortably with a full kitchen, Smart TVs, and dedicated parking.

Bethany Bay. Sleeps 4. AC, Pool, Ground Floor
Unit 6302 at Bethany Bay is a 2 BR, 2 Bath, ground floor unit with panoramic views of the waterways and Indian River Bay. Sleeps 4. Free parking. Fully equipped kitchen, AC, fireplace, community outdoor pool, jogging/hiking path, 9 hole golf course. NON-SMOKING UNIT. Enjoy dinner and drinks on the enclosed rear porch and take in the view. 5 miles to Bethany Beach, 12 miles to Ocean City, 17 miles to Rehoboth Beach. I will allow one dog and the pet fee is $200.

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 and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

Bayside Retreat in the Heart of Ocean City!
Newly renovated condo!! -Water view. Watch the boat traffic. -Oversized balcony with comfortable seating. -Comfy LoveSac couch. -Walk to boardwalk or beach - 15 minutes. -Walk to Jolly Roger amusement park. -Fish off community dock down below unit. -Close to dining and shopping. -Kitchenette for cooking meals. -Fast Wifi and Streaming TVs. -Fully Stocked Home. Clean linens, towels, toilet paper, paper towels & more!

One Bedroom Beachfront Apartment Mid-Town
Midtown serves as the intersection between the vibrant inlet and boardwalk and the serene North Ocean City. In addition to stunning views of the beach and impressive hotels and condos, it also provides easy access to a wide range of activities, restaurants, shops, and attractions that cater to individuals of all age groups.
Popular amenities for apartment rentals near Chesapeake Bay
Weekly apartment rentals

Rehoboth Ave Boardwalk, Ocean & Bandstand Views U2

Lovely Ocean Block 1 BR near Convention Center!

Cozy oceanfront condo with stunning ocean views

On the Bay, Private Beach-Boat Slip

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

Mid-Town OC! Ocean Block... Steps to the Beach!

Oasis by the Ocean - Direct Oceanfront

Beautiful Renovated Ocean Front Condo 1b/1.5ba
Pet-friendly apartment rentals

Lovely 2level Condo Steps 2Beach+Pool

Renovated Apt In Historic Dist w/2 Parking Spots

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

Read Ave Dewey Condo - Bay Front, Private Beach

Perfect location!

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

Lux Direct Oceanfront*Deck*Pets welcome*Arcade*

Cozy Old Town Apartment
Apartment rentals with a pool

Right on Silver Lake walk to the beach and town!

Oceanfront Family Oasis: Pool, Beach & Parking!

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Renovated Condo Near Outlets, 3.5 Miles to Beach

Love Above the Waves-Best Ocean View & Heated Pool

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

Water Front Condo w/Pool Short Walk to Beach
Private apartment rentals

Le Petit Paradis-Waterfront, pet-friendly Studio

Ocean Block | Sunchaser Condo | Surfer's Dream

La Pescadora - Cozy. Coastal. Completely Yours.

Annapolis @Gate 1 steps to the Harbor Free parking

Condo in Downtown Rehoboth, with bikes

Your Hideaway awaits/1-bedroom downtown pad.

Barnyard Retreat

Direct Oceanfront Boardwalk - Steps To The Beach
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 £30 per night before taxes and fees

Verified guest reviews
Over 5,680 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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