
Condo rentals near Chesapeake Bay
Find and book unique condos on Airbnb
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 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 Riverfront Condo w/ sunrise & sunset views
Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

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..

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).

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.

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE
2 Bedroom Condo Top Floor (3rd Floor) - Waterfront in Lewes/Rehoboth Beach DE Great Scenery Views - The Residence at Rehoboth Bay. *Community Pool available during in-season (8am-8pm) *No cleaning fee Nearby amenities and attractions include: Rehoboth Beach Boardwalk (6 Miles) Cape Henlopen State Park (8 Miles) Dewey Beach, DE (7 Miles) Bethany Beach, DE (18 Miles) Ocean City, MD (32 Miles) Shopping Outlets (4 Miles)

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!

Chic's Beach Rental and Fishing
Duplex on Chic's Beach, expansive water view and private beach access right out the back door. Everything needed for the House & Beach included, including Coffee. We also offer Fishing Trips, Fish for Sale, Dolphin Cruises and Seafood & Greek Dinners! Michael Griffith, President/Manager, Chic's Beach Rental and Fishing LLC

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.

Lovely 1 bedroom condo/only 2 blocks to the beach
Enjoy a wonderful experience at this centrally-located place only two blocks away from the beach and Ocean City boardwalk. Newly remodeled condo in a great location within a walking distance to many amazing restaurants and bars, convenience stores, amusement park, mini-golf, boutiques, playground...
Popular amenities for condo rentals near Chesapeake Bay
Weekly condo rentals

Lovely Ocean Block 1 BR near Convention Center!

Beachfront Getaway, Pet Friendly, Mermaid Suite

Right on Silver Lake walk to the beach and town!

☀️ Ocean block | Midtown OCMD

On the Bay, Private Beach-Boat Slip

Beach Retreat: Easy Walkable Living, Bikes, Coffee

Steps to Ocean! Beach Accessories. Uncrowded Beach

Renovated Condo Near Outlets, 3.5 Miles to Beach
Pet-friendly condo rentals

Kingsmill 1bed/1ba on Golf Course 9th Fairway

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

Spacious Family Retreat Centrally located

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

Cozy Lewes Retreat | Pool, Short Drive to Beaches
Condo rentals with a pool

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Boutique Moments OC • Pool • Walk to Boardwalk

Villa Del Sol, Beautiful stay near beaches/outlets

Salt Air Retreat - Rehoboth Beach

10 mins to beach-2 BR-Sleep Six-Pool-Beach PK pass

Sunset Beach Condo

White Marlin 107 Renovated Amazing Bay Views Pool

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

Studio | Walk to Beach | Free Parking | Balcony

Rehoboth Ave Boardwalk, Ocean & Bandstand Views U2

Gem in the Heart of the Fan #3!

Historic Federal hills urban lifestyle

Steps to Beach & Boardwalk

Barnyard Retreat

STEPS to the BEACH! Perfect Mid-Town Location!

Coastal Condo Near Rehoboth Beach and Lewes.
Quick stats about condo rentals near Chesapeake Bay

Total holiday rentals
Explore 140 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $51 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
130 of Chesapeake Bay holiday 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!
Destinations to explore
- Private suite rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Rentals with a home theatre Chesapeake Bay
- Villa rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- House rentals Chesapeake Bay
- RV rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Holiday home rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Condo rentals United States
- Busch Gardens Williamsburg
- Virginia Beach Oceanfront
- Chincoteague Island
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- First Landing Beach
- Hampton University
- Town Point Park
- Old Dominion University
- Chrysler Hall
- Virginia Living History Museum
- Neptune's Park
- USS Wisconsin (BB-64)
- Harbor Park




