
Condo rentals near Chesapeake Bay
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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!!
4.99 out of 5 average rating, 149 reviews
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.
4.86 out of 5 average rating, 294 reviews
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.
4.96 out of 5 average rating, 239 reviews
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.
4.99 out of 5 average rating, 118 reviews
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.
4.95 out of 5 average rating, 322 reviews
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.
4.98 out of 5 average rating, 130 reviews
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.
4.96 out of 5 average rating, 126 reviews
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.
4.96 out of 5 average rating, 190 reviews
Renovated Apt In Historic Dist w/2 Parking Spots
Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens , lucid mattresses, Keurig coffee bar, toiletries. Walk to town in 10 min or less or take the free trolley to Main St, USNA, Churches, AYC. No children under 12.
4.94 out of 5 average rating, 451 reviews
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.
4.96 out of 5 average rating, 172 reviews
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.
5.0 out of 5 average rating, 122 reviews
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.
4.99 out of 5 average rating, 111 reviewsPopular amenities for condo rentals near Chesapeake Bay
Weekly condo rentals

Luxury Riverfront Condo w/ sunrise & sunset views
4.93 out of 5 average rating, 152 reviews
CANAL FRONT Wi-Fi, Roku, Netflix, boatslip, pool
4.9 out of 5 average rating, 364 reviews
Oceanfront Family Oasis: Pool, Beach & Parking!
4.9 out of 5 average rating, 365 reviews
2 Bedroom Stylish Kingsmill condo
4.95 out of 5 average rating, 154 reviews
Cozy Old Town Apartment
4.98 out of 5 average rating, 143 reviews
Beach Sunrise: Walk to Downtown & Lewes Beach
4.98 out of 5 average rating, 368 reviews
Villa Del Sol, Beautiful stay near beaches/outlets
4.97 out of 5 average rating, 241 reviews
Annapolis Waterfront Condo - Unit #: A-203
4.97 out of 5 average rating, 345 reviewsPet-friendly condo rentals

Bright, large zen studio on historic Logan Circle
4.89 out of 5 average rating, 533 reviews
Sojourn in DuPont Circle: Modern Meets Historic
4.89 out of 5 average rating, 105 reviews
DirectOceanFront on Boardwalk/Newly Remodeled/Pool
4.78 out of 5 average rating, 240 reviews
Sweet getaway - beach block, steps from the beach!
4.97 out of 5 average rating, 339 reviews
New, Sunny, 2BR - Parking, Patio, Firepit
4.9 out of 5 average rating, 279 reviews
Modern Oceanside 42nd st 2bed 2bath Sleeps 6 to 8.
4.93 out of 5 average rating, 216 reviews
Read Ave Dewey Condo - Bay Front, Private Beach
4.87 out of 5 average rating, 232 reviews
Entire 2 Bedroom/ 2 Bathroom unit (Heart of SHAW)
4.97 out of 5 average rating, 211 reviewsCondo rentals with a pool

Renovated Condo Near Outlets, 3.5 Miles to Beach
4.98 out of 5 average rating, 220 reviews
Ocean Block - Clean, cozy 1 Bedroom. Pool, Wifi
4.84 out of 5 average rating, 144 reviews
Completely Renovated Luxury Bay Front Condo
4.97 out of 5 average rating, 107 reviews
Consistent 5-star rating Lakefront 3BR & 2BA condo
4.94 out of 5 average rating, 147 reviews
Sunrise Studio - Ocean Front, on Boardwalk, Pool!
4.94 out of 5 average rating, 198 reviews
Beach Paradise 202-Downtown Luxury Condo Bay View
4.9 out of 5 average rating, 198 reviews
Beautiful condo in Villages of Five Points, Lewes
4.95 out of 5 average rating, 159 reviews
Oceanfront Studio: Boardwalk, Beach, & Pool Views
4.97 out of 5 average rating, 153 reviewsPrivate condo rentals

Beach Bungalow on the Boardwalk
4.86 out of 5 average rating, 180 reviews
Stylish Apartment Steps From the Beach
4.98 out of 5 average rating, 203 reviews
A bit of Paradise
4.86 out of 5 average rating, 340 reviews
The Loft at Lakeside
4.93 out of 5 average rating, 183 reviews
Light and Airy Oceanfront Condo with Large Porch
4.92 out of 5 average rating, 914 reviews
Rehoboth Ave Boardwalk, Beach & Bandstand Views U2
4.75 out of 5 average rating, 289 reviews
Cozy studio for your getaway
4.89 out of 5 average rating, 101 reviews
Station House West: Upscale Condo in Cambridge, MD
4.92 out of 5 average rating, 37 reviewsQuick 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!
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