
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!!

Newly Renovated & Modern 1BR Condo - Unit 2
Completely renovated, stylishly furnished condo unit in Arlington, VA just one stoplight from Washington DC, the Pentagon, Clarendon, Crystal City and National Airport. Spacious unit with free cable TV, secure Internet/Wi-Fi, FREE RESERVED PARKING space in private lot, in-unit Washer/Dryer, Full Kitchen. Steps away from public transit buses that route to multiple Orange/Blue/Silver line Metro train. Comfortably accommodates the traveling professional, those on vacation and is kid friendly.

Beautiful waterview 2B condo w/Dock&Close to Beach
Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!

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.

Coastal Modern Condo • Balcony, 2 Baths, East Rt 1
☀️ Your Rehoboth Beach Escape Why guests love staying here: • Community pool 🌴 • 2 full baths • Private screened balcony 🌿 • East of Route 1 • Strong central AC ❄️ • Split-bedroom layout for added privacy • Beach chairs & towels included 🏖️ • Fast WiFi + smart TVs • Plenty of FREE parking • In-unit washer & dryer • Minutes to beaches, boardwalk, restaurants & shopping • Quiet community close to everything Perfect for couples, families, girls’ weekends, and relaxing coastal getaways.

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, KING bed, 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.

Ocean Side 1BR / 1.5BA Renovated Modern Condo
Ocean Side! Two minute walk to the beach! Fully renovated. Bright, modern, clean condo. First floor. Located in the heart of Ocean City ( Midtown ) in walking distance from restaurants, bars, shops, and public transportation. Brand new appliances and furniture. Free WiFi, King Size Bed, 65" TV (living room) & 50" TV bedroom. Pullout Queen Sofa, Brand New Full Bathroom + Half Bathroom, Washer and Dryer in the unit. Keurig Coffee, 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 (limited access) and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

The Loft 2B/2BA minutes to Rehoboth & Lewes Beach
Escape to a stylish coastal 2 bedroom 2 bath condo designed for relaxing beach vacations, family trips, and weekend getaways. Conveniently located just minutes from Rehoboth Beach and Lewes, The Loft offers the perfect combination of comfort, convenience, and coastal charm. Whether you're planning a family beach trip, a couples retreat, shopping weekend, or exploring Delaware’s beautiful coastline, you'll have everything you need for a memorable stay.

Oceanfront Family Oasis: Pool, Beach & Parking!
Escape to your dream family vacation in this amazing 2-bedroom condo on the 8th floor! Enjoy incredible ocean views, direct beach access, and proximity to Ocean City's top attractions like the vibrant OC Boardwalk and thrilling amusement parks. This condo offers modern amenities, a refreshing seasonal outdoor pool, and the convenience of free parking. Perfect for families seeking fun and relaxation near the ocean.

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

Cozy Old Town Apartment

Modern & Cozy Retreat | Pool | Close to Beaches

Light and Airy Oceanfront Condo with Large Porch

Coastal and Bright Oceanfront Condo

Annapolis Waterfront Condo - Unit #: A-203

The Grand Delphey: Downtown Modern Penthouse

Bayside Retreat in the Heart of Ocean City!

Renovated Apt In Historic Dist w/2 Parking Spots
Pet-friendly condo rentals

Sojourn in DuPont Circle: Modern Meets Historic

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

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

Sweet getaway - beach block, steps from the beach!

New, Sunny, 2BR - Parking, Patio, Firepit

Peaceful patio condo

Modern Oceanside 42nd st 2bed 2bath Sleeps 6 to 8.

Beautiful Upper Level 1BR in Downtown DC
Condo rentals with a pool

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Consistent 5-star rating Lakefront 3BR & 2BA condo

Beach Paradise 202-Downtown Luxury Condo Bay View

Renovated Condo Near Outlets, 3.5 Miles to Beach

Villa Del Sol, Beautiful stay near beaches/outlets

Newly Renovated Modern 2 Bed/2 Bath Condo w/ Pool

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Water view at Ocean Pines Yacht Club Condo
Private condo rentals

Luxury Riverfront Condo w/ sunrise & sunset views

Ocean Block | Sunchaser Condo | Surfer's Dream

The Hideaway By The Bay OCMD

Beautiful Renovated Ocean Front Condo 1b/1.5ba

Rehoboth Ave Boardwalk, Beach & Bandstand Views U2

La Pescadora - Cozy. Coastal. Completely Yours.

The Drinking Gourd: Stunning Cambridge Penthouse

The Solomons Sunrise Suite
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 $17 NZD 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
- Private suite rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- House rentals Chesapeake Bay
- RV rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Holiday home rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Condo rentals United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Town Point Park
- Nauticus
- Chrysler Museum of Art
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- Mount Trashmore Park
- USS Wisconsin (BB-64)
- Sandy Bottom Nature Park





