
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.

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.

Renovated Condo Near Outlets, 3.5 Miles to Beach
Enjoy your stay in this recently renovated and beautifully furnished two-bedroom, two-bathroom 3rd-floor condo conveniently located 3.5 miles from the Rehoboth Beach boardwalk, and 4.5 miles from Lewes Beach. The proximity to the beaches, stores, and restaurants make this condo a great spot to spend a fun-filled vacation at the beach. Our condo amenities include a community pool*( seasonal), free parking, free WiFi, smart TV, washer, and dryer. We supply all the sheets & towels for your stay.

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.

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

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.

Modern & Cozy Retreat | Pool | Close to Beaches
Enjoy a relaxing Lewes getaway nestled just off Coastal Highway, with easy access to beaches, dining, and local attractions. Less than 5 miles to Lewes Beach and less than 7 miles to Rehoboth and Dewey Beach, making it easy to enjoy the ocean, boardwalk, and everything the area has to offer. Just minutes from Nassau Valley Vineyards, Georgetown-Lewes Trail, Cape Henlopen State Park, historic downtown Lewes, great restaurants, breweries, and tax-free shopping at Tanger Outlets.

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).

Bethany Bay. Sleeps 4. AC, Pool, Ground Floor
Unit 6302 at Bethany Bay is a 2 BR, 2 Bath, ground floor unit with panoramic views of the waterways and Indian River Bay. Sleeps 4. Free parking. Fully equipped kitchen, AC, fireplace, community outdoor pool, jogging/hiking path, 9 hole golf course. NON-SMOKING UNIT. Enjoy dinner and drinks on the enclosed rear porch and take in the view. 5 miles to Bethany Beach, 12 miles to Ocean City, 17 miles to Rehoboth Beach. I will allow one dog and the pet fee is $50 per night.

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.

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

Water view at Ocean Pines Yacht Club Condo

Luxury Riverfront Condo w/ sunrise & sunset views

The Grand Delphey: Downtown Modern Penthouse

Renovated Apt In Historic Dist w/2 Parking Spots

Anchors Away

A bit of Paradise

Villa Del Sol, Beautiful stay near beaches/outlets

Bayside Retreat in the Heart of Ocean City!
Pet-friendly condo rentals

Hill East BnB - Modern Style and Comfort 3BR/3BA

Bright, large zen studio on historic Logan Circle

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

Sojourn in DuPont Circle: Modern Meets Historic

Read Ave Dewey Condo - Bay Front, Private Beach

Beautiful 2BR/1BA Renovated Condo near DC

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

Kingsmill 1bed/1ba on Golf Course 9th Fairway
Condo rentals with a pool

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

2BR Coastal Escape with Pool Near Rehoboth Beach

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

Right on Silver Lake walk to the beach and town!

Beautiful condo in Villages of Five Points, Lewes

First Floor Comfort and Convenience

Captains Quarters | Waterfront & Pool

Stress-Free Family Beach Stay | Pool + Kid Perks
Private condo rentals

Best Value Condo in Downtown Norfolk

2BR Coastal Retreat Walk to Beach & Downtown Lewes

Rehoboth Ave Boardwalk, Beach & Bandstand Views U2

Cape Suites Room 1 - Free Parking!

The Drinking Gourd: Stunning Cambridge Penthouse

Beach Haven Hideaway ~ stunning water views!

The Solomons Sunrise Suite

Bayfront Boardwalk Condo w/ Sunrise Views
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 $14 CAD per night before taxes and fees

Verified guest reviews
Over 5,840 verified reviews to help you choose

Family-friendly vacation rentals
100 properties offer extra space and 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

Wifi availability
130 of Chesapeake Bay vacation rentals include wifi 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
- Rentals with a hot tub Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Vacation 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
- Villa rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with pools 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
- Fort Monroe National Monument
- USS Wisconsin (BB-64)





