
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 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!

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).

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!

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.

Beach Camp Lewes: Bikes, Beach Chairs & Coffee
Start your morning at Beach Camp with a fresh brew from our coffee bar before taking a walk to see a beach sunrise. After a day of exploring the pristine trails and wildlife of Cape Henlopen on our complimentary cruiser bikes, skip the "camp cooking" and walk 2 minutes into town for a five-star meal. We’ve provided the bikes and the beach chairs—all you need to bring is your sense of adventure.

Gem in the Heart of the Fan #3!
My newest listing is ready to go (June 2020). And with a beautiful hand painted mural to boot. Same great building close to everything in the fan. Just steps from Monument Avenue, VCU, and tons of great restaurants too! Walking distance to Scotts Addition, Carytown, and all the other ‘Fan’ fun Richmond has to offer! Longer walk or quick uber or GRTC to Broadberry, Altria or the National.

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

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

The Loft 2B/2BA minutes to Rehoboth & Lewes Beach

Annapolis @Gate 1 steps to the Harbor Free parking

2 BdrmOceanfront-Pool, Xbox, Pickleball, Gym, WiFi

Newly Renovated & Modern 1BR Condo - Unit 2

Bayside Retreat in the Heart of Ocean City!

One Bedroom Beachfront Apartment Mid-Town

*Steps to Sea* 45th & Ocean Block W/ Amenities

Luxury Oceanfront Escape!
Pet-friendly condo rentals

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

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

Renovated Apt In Historic Dist w/2 Parking Spots

Peaceful patio condo

Bright, large zen studio on historic Logan Circle

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

Cozy Condo 2BR/2BA close to Outlets & Beaches

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

Designer Oceanfront Condo | Pool, Hot Tub & Deck

Direct Oceanfront with a View and Amenities Galore

1st Floor Condo in Annapolis

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

OceanfrontJewel|DirectOceanView•NewlyRenovatedPool

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Clean and Comfy, Close to Beach and Shopping

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

Your Hideaway awaits/1-bedroom downtown pad.

The Loft at Lakeside

Steps to Ocean! Beach Accessories! Uncrowded Beach

Beach Haven Hideaway ~ stunning water views!

The Solomons Sunrise Suite

The Drinking Gourd: Stunning Cambridge Penthouse

La Pescadora - Cozy. Coastal. Completely Yours.

Mod 1BR Downtown |SofaBed| FreePark|Near Hospital
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 $14 AUD per night before taxes and fees

Verified guest reviews
Over 5,840 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

4.8 Average rating
Chesapeake Bay stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Beach house rentals Chesapeake Bay
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- Condo rentals United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- First Landing Beach
- Neptune's Park
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Nauticus
- Town Point Park
- Virginia Living History Museum
- Mount Trashmore Park
- USS Wisconsin (BB-64)
- Chrysler Hall
- Sandy Bottom Nature Park
- The NorVa
- Willoughby Beach
- Hampton Coliseum





