
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!!

Gorgeous, large, modern 1 BR on Hist. Logan Circle
Gorgeous, bright, open plan nearly 1,000 square foot 1 bedroom condo with space for an entire family in historic Logan Circle neighborhood on a quiet street. Short walk to White House, Mall & museums. Built in 1900, this brownstone was thoughtfully renovated to blend modern (in-ceiling lighting, stainless steel appliances, bamboo flooring) with historic features (original exposed brick & trim). Warm, spacious & comfortable for your stay. Logan is DC's hottest & hippest area with a 96 walk score.

Coastal 2BR • 10 min to Beach & Trails
Welcome to The Loft, a cozy Rehoboth Beach retreat. Feel right at home in this spacious 2BR, 2BA condo conveniently located East of Rt. 1 between Rehoboth Beach and Lewes Beach. The condo is also just minutes from Junction & Breakwater Trail, Georgetown Lewes Trail and Cape Henlopen State Park... perfect for walks and biking. Love shopping? There are 3 Tanger Outlets and an abundance of other stores. Explore endless dining options in downtown Rehoboth Beach, Lewes and all along Coastal Highway.

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!

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 :)

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 Loft at Lakeside
Welcome to the The loft at Lakeside! The loft is a completely separate space that comes with its own entrance and parking space. The loft consists of a spacious bedroom with a walk-in closet. There is a full bathroom in the bedroom and a half bath near the kitchen. The main space consists of spacious Kitchen that sits right next to the cozy family room, with a large couch. It also has a full laundry room for anyone looking to take home clean clothes after an amazing stay at The Loft.

Your Hideaway awaits/1-bedroom downtown pad.
There is no place like home when you visit our cozy 1 bed/1 bath abode! This 2nd floor unit is nestled in the rear of a historic home that has been converted into condo living. This space checks all the boxes for a weekend getaway or long-term stay. Enjoy an open living/dinning area, a new memory foam king bed, & a fully furnished bathroom! We offer a keyless entry & 1 parking spot - a rarity for downtown living. Residents live above & below. NO pets, loud music, or parties.

Oceanfront 1 Bedroom, Pool, Ocean & Bay Views
OVERSIZE one-bedroom plus TWO large 3-season rooms! The back balcony is filled with expansive ocean views from every angle and sliding windows, and the front porch looks out to the bay - wonderful atmosphere in the quiet north end. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Washer/Dryer in unit - Keyless check-in 24/7

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.

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.
Popular amenities for condo rentals near Chesapeake Bay
Weekly condo rentals

One Bedroom Beachfront Apartment Mid-Town

Capts Qrtrs - Awesome downtown Annapolis location!

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

1 Bedroom 1 Bath Condo on Silver Lake

2 Bedroom Stylish Kingsmill condo

Chic's Beach Rental and Fishing

Newly Renovated & Modern 1BR Condo - Unit 2

Direct Oceanfront close to Northside Park!
Pet-friendly condo rentals

Lovely Condo Steps 2Beach+Pool Unlimited Parking

Renovated Apt In Historic Dist w/2 Parking Spots

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

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

Elegant Condo with a Spacious Porch

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

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

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC
Condo rentals with a pool

Luxe Oceanfront 1BR | Pool, Hot Tub, Sun Deck

Stress-Free Family Beach Stay | Pool + Kid Perks

Right on Silver Lake walk to the beach and town!

Cozy Condo on Silver Lake - Walk to the beach!

Oceanfront Bldg.| 2 pools | Tennis | Game Room

Clean and Comfy, Close to Beach and Shopping

Beach condo w/pool! All linens & beach supplies

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen
Private condo rentals

BeachBox II • Panoramic Inlet Views • Free Parking

Comfy 1BR w pond view Kingsmill

Ocean block condo

Harbor Gem

Downtown Condo, Parking, Walk to Beach & Boardwalk

Beach Bungalow on the Boardwalk

Direct Oceanfront Boardwalk - Steps To The Beach

Oceanside Charm, desirable midtown Ocean City, MD
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 $50 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
- Bed and breakfasts Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- House rentals Chesapeake Bay
- RV rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Rentals with a home theatre Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Holiday home rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Condo rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Grommet Island Park
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Old Dominion University
- Neptune's Park
- Kiptopeke Beach
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- Nauticus
- Town Point Park
- Virginia Zoological Park
- Virginia Living History Museum
- The Mariners' Museum
- Cape Henry Light House





