
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 New Beachfront! King Bed, Direct Sea 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.

The Grand Delphey: Downtown Artist Retreat
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 shared 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!

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.

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 :)

Beautiful Renovated Ocean Front Condo 1b/1.5ba
Beautiful renovated ocean front condo. Get ready to relax in comfort and style! This large 836 sqft one 1b/1.5ba offers breath taking views of the ocean. You will be just steps away from the sand in one of the closest buildings to the beach. Enjoy your coffee or a different sunrise each day from your private balcony off the living room. Updated patio furniture with a cozy bench and high table with 2 chairs that bring a spectacular, completely unobstructed view of the beach and ocean.

Dewey Beach Condo 2BR+sleeper. Walk to the beach!
2 BR, ground floor condo on the south side of Dewey Beach! 1.5 blocks to the beach, 1 block south to beautiful bayside dining. Discounts for stays over 3 nights! The HOA maintains a relaxing, clean, family friendly atmosphere. Self check-in keypad code auto-sent upon booking. Professionally cleaned and beds made before your check in. Bed linens, shower towels/essentials, 2 Dewey Beach Street Parking Passes, and beach chairs are provided free of charge. Max occupancy of 6 at all times.

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.

Beach Camp: In-Town Lewes Walk to All
The perfect in-town Lewes (loo-iss) location. Explore scenic Coastal Delaware. ✔ Walk Downtown - Restaurants, shops, parks - 2 minute walk ✔ Walk or bike to Lewes Beach - Less than a half mile ✔ Bike Trails - Plenty of options at your fingertips ✔ Cape Henlopen State Park - Less than 2 miles ✔ Easy electronic keypad entry ✔ Fast Gigabit X2 Speed Wi-Fi (2100 Mbps) ✔ Roku Smart TV with free YouTube tv cable channels ✔ Parking is plentiful *Bonus* Two complimentary bicycles provided

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.

Sixteen West - Modern Apartment in Richmond
Welcome to Sixteen West! This stylish, modern apartment is nestled in the heart of historic Jackson Ward. Recently renovated, the space features beautiful hardwood flooring, updated lighting fixtures, and a sleek, fully equipped kitchen. You'll be within walking distance of some of Richmond’s best spots, including Tarrant's Café, Quirk Hotel, The National, and more! Please note: This unit requires climbing 2.5 flights of stairs — THERE IS NO ELEVATOR.

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 and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.
Popular amenities for condo rentals near Chesapeake Bay
Weekly condo rentals

Beach Paradise 202-Downtown Luxury Condo Bay View

Bijou Space in Downtown Bethesda

Cozy Oxford Getaway

Bayside Retreat in the Heart of Ocean City!

2b 2b condo! 2 master bedrooms! rehoboth beach

Private Apt-Old Town Alexandria-Self Check In

Newly Renovated & Modern 1BR Condo - Unit 1

☀️ Enjoy the Beachlife!! —>2Bed & 2Bath Condo ☀️
Pet-friendly condo rentals

New Downtown Annapolis Condo With Free Parking

Luxury water-view condo with high-end finishes

Spacious Bloomingdale 1BR; garage parking included

Renovated Apt In Historic Dist w/2 Parking Spots

Walk to beach lovely 2/2 in "Kingsmill on James"

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC

Spacious| Modern & Cozy| Pool| Close to the Beach

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

PENTHOUSE - 8TH Floor Boardwalk/Epic Views/Pool/

Family Friendly Top Floor Condo Near Boardwalk

Kingsmill 1bed/1ba on Golf Course 9th Fairway

Oceanfront Family Oasis: Pool, Beach & Parking!

Oceanfront Gem VaB Studio Exceptional Views

Comfy and Convenient 2 bedroom/2 bath condo

Beautiful 2BR 2BA oceanfront condo at the Atlantis

Ocean Pines marina view condo
Private condo rentals

The Bird's Nest in Historic Occoquan (Mins to DC)

Comfy 1BR w pond view Kingsmill

Direct Oceanfront Condo with Expansive Ocean Views

Cozy Capitol Hill Row Home

Downtown 1 BR Condo Steps to Everything

Barnyard Retreat

Mid-Town OC! Ocean Block... Steps to the Beach!

Beach Condo Block Off Oceanfront!
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 $67 NZD per night before taxes and fees

Verified guest reviews
Over 5,680 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, Wi-Fi 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
- Rentals with a fire pit Chesapeake Bay
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- Condo rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Buckroe Beach
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- First Landing Beach
- The NorVa
- Chrysler Hall
- Nauticus
- Virginia Zoological Park
- Old Dominion University
- Hampton University
- Virginia Living History Museum
- Town Point Park
- USS Wisconsin (BB-64)
- Colonial Williamsburg's Merchants Square
- Neptune's Park




