
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.

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 Artist Retreat
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 shared 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!

Lovely beach-front condo with pool and views
Kick back and relax in this calm, stylish space. This one-bedroom condo is the perfect space for 1-2 couples, or a family. You have floor-to-ceiling beach views, plus amazing sunrises and sunsets from the two separate balconies. The kitchen is well equipped to cook every meal, or eat out at Ocean City's many restaurants. Your stay also comes with 4 pool passes for accessing the onsite seasonal outdoor pool (viewable from the unit) and access to the building’s tennis/pickleball courts!

OceanfrontStudio-Slps4-Pool-Pickleball-HBOMax-Dis+
Absolutely stunning studio condo in the iconic Golden Sands! Private balcony offers amazing direct ocean views, and overlooks the building's sun deck. Updated kitchen with stainless steel appliances. Murphy bed & sofa bed allows the unit to sleep 4 comfortably. Includes HBOMAX, Disney+, and electric fireplace. Stylish bathroom with toilet and shower conveniently separated from sink. Building offers restaurants, pools, game rooms, and more! Golden Sands has a $75 registration fee.

The Bird's Nest in Historic Occoquan (Mins to DC)
Spacious condo in the heart of walkable historic Town of Occoquan. Second floor loft with full kitchen, bath, a comfortable queen bed, work station, w/d in unit & one free parking spot. The Town of Occoquan offers unique experiences (kayaking, fishing, birdwatching and shopping) all within walking distance. Excellent dining choices from award winning restaurants to casual eateries. Mins to I-95, 123, VRE. D.C. (35min); Quantico (25min); Potomac Mills (10min). Tysons (25min).

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.

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, 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.

Funky Uptown Apt meets Downtown - Hist District
Location location location where Uptown meets Downtown in the Historic District. 1/2 block to Dinner Under The ✨ , First Sunday Arts. Tsu, 49 West, Level in the front yard Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Eastport) is walking distance from this unique 2nd floor unit w elevated deck for morning coffee as Jazz wafts in, full kitchen, w/d, clawfoot shower/tub, MBR with Queen.

Bayside Bliss - Renovated Downtown Condo w/ Porch
Welcome to Bayside Bliss, a stylish 2BR / 2BA top floor condo in Downtown OC. Relax in the oversized living room, stream your favorite shows and music to any of the smart tvs, or watch the sunset on the porch. The fully equipped kitchen, washer & dryer, and two full bathrooms will make your stay feel like home. Just a short walk to some of OC's best restaurants, nightlife, the boardwalk, and the beach. Steps away from the White Marlin Open weigh-ins and OC Air Show

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.

Beachfront Getaway, Pet Friendly, Mermaid Suite
Escape to a serene, semi-private beach with breathtaking views and everything you need for the perfect vacation. Welcome to Big Blue, where unforgettable memories await. Beach access, Fully stocked kitchen, modern upgrades, comfy beds, large open floor plan, bbq pit, outdoor patio, beach gear & many personal touches. Condo not suitable for children under 7. Pet fee $100 for max of 2 with approval.
Popular amenities for condo rentals near Chesapeake Bay
Weekly condo rentals

One Bedroom Beachfront Apartment Mid-Town

Lovely Ocean Block 1 BR near Convention Center!

Historic Federal hills urban lifestyle

Summer Palace in Ocean city .

On the Bay, Private Beach-Boat Slip

Steps to Ocean! Beach Accessories. Uncrowded Beach

Newly Renovated & Modern 1BR Condo - Unit 2

Oasis by the Ocean - Direct Oceanfront
Pet-friendly condo rentals

Bright, large zen studio on historic Logan Circle

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

Fan District Gem | Walk to VCU | King Bed| Parking

Cozy Condo Oasis with Adorable Private Patio

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

Boutique Moments OC • Pool • Walk to Boardwalk

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Steps to Beach, Pool, Family Friendly with Linens

Oceanfront Family Oasis: Pool, Beach & Parking!

Cozy oceanfront condo with stunning ocean views

Clean and Comfy, Close to Beach and Shopping

Renovated Condo Near Outlets, 3.5 Miles to Beach

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

La Pescadora - Cozy. Coastal. Completely Yours.

Old School Beach Cottage-Oceanside Condo

2 Bedroom Stylish Kingsmill condo

Coastal Condo Near Rehoboth Beach and Lewes.

Direct Oceanfront close to Northside Park!

Sixteen West - Modern Apartment in Richmond

Luxury Oceanfront Escape!

Quiet Ocean Front Retreat
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 G$6,276 GYD per night before taxes and fees

Verified guest reviews
Over 5,600 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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