
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.

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 Apt In Historic Dist w 2 Parking Spots
Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end, brand new 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 10.

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC
Location, location, location. Bright one bedroom condo in prime downtown Bethesda location with designer furnishings. One of the best 1 bedrooms in the building with the best balcony location right off Bethesda Row. Easy walking distance to Metro and includes one of the best underground parking spaces by elevator. Lobby was recently renovated and gym has all new gym equipment. NOTE - key is provided through a lockbox (rather than in person) and will need to be returned back to lockbox.

Luxury Riverfront Condo w/ sunrise & sunset views
Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

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, BR2 with Full. LR w/sofa

Annapolis Waterfront Condo - Unit #: A-203
BOOK NOW SUMMER 2026 SPRING and FALL BOAT SHOW 1 bed/bath condo, sleeps 4 max, covered comfortable water facing deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy Football, .25 mi. to boatshows! Great views - 2nd flr. condo (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 location.

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.

Casa 1776 - Spacious Apartment | Heart of Downtown
Rest in the heart of downtown Fredericksburg! You’ll stay in the lower level apartment of this historic home. Constructed during the Revolution, and used as a hospital during the Civil War, this home is directly across from the visitor center, within steps of landmarks, awesome restaurants, taprooms, and shops. It’s the perfect spot for a weekend away or historic excursion. The newly constructed River Front Park sits at the rear of the property and is awesome for the little ones.

Beach Camp * Free Bikes * Top Restaurants
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 Speed Wi-Fi (950/880 Mpbs) ✔ Roku Smart TV with free YouTube tv cable channels ✔ Parking is plentiful *Bonus* Two complimentary bicycles provided

Remodeled 1BR/1BA Condo: close to DC with pool!
Spacious and completely remodeled condo at Fairfax Heritage. Newly painted and featuring brand new carpet and vinyl flooring throughout the unit. All-new kitchen including stainless steel appliances, cabinets, quartz countertops, sink, lighting and plumbing fixtures. Remodeled bath. Generously-sized bedroom with double closet. Large private balcony overlooking treed courtyard. Common laundry on lower level, private storage unit. Grilling available in picnic area.

DC’s Southwest and Navy Yard Welcomes You!
Minutes from the Nationals Stadium, Metro and near DC’s premier Waterfront-Wharf and Navy Yard! Enjoy this unique row house in the amazing neighborhood of Southwest. This rowhouse was our home and we’re excited to have you experience your stay here! The condo is located 1 block from the Navy Yard and Nationals Stadium, and one mile away from the Capitol if you’re looking to visit DC tourists attractions. It has easy access to Metro stations with a 5 minute walk.

Cozy Private Condo in Mt. Vernon with Rooftop
This cozy private condo is located in the hip/historic Mt. Vernon neighborhood, and within walking distance to numerous bars, breweries, and museums. Conveniently located right near the highway (I-83) and Penn Station, it's also a quick walk down to the Inner Harbor (only 1 mile away), and a short Uber ride to Fells Point & Fed Hill. Condo includes a 12th floor rooftop overlooking the city with amazing views. UPDATED - high speed WiFi currently available.
Popular amenities for condo rentals near Chesapeake Bay
Weekly condo rentals

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

Private Deck | Skylights | Free Parking | Downtown

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

Charming Annapolis Waterfront Condo

Lux in heart of DC social scene, free parking!

Spacious Rental - Winterfest of Lights 11 mi.

Private Apt-Old Town Alexandria-Self Check In

Modern 2 bed 2 bath unit in hip DC neighborhood
Pet-friendly condo rentals

Spacious Bloomingdale 1BR; garage parking included

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

Best Location EVER! 2BR/2BA, Pet friendly

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

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

Quiet Stay + Huge Apt + Hot Tub + Dogs, Walkable

Family Friendly HQ - Historic DC 3BR & 3BA

Spacious| Modern &Cozy| Pool| Close to the Beaches
Condo rentals with a pool

Family Friendly Top Floor Condo Near Boardwalk

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Oceanfront Gem VaB Studio Exceptional Views

Oceanfront Studio: Boardwalk, Beach, & Pool Views

White Marlin 107 Renovated Amazing Bay Views Pool

Mimi’s Place @ The Villages of 5 Points in Lewes

Clean and Comfy, Longer Term Stay available, Quiet
Private condo rentals

High Tech Hideaway: The modern beach lifestyle

Bijou Space in Downtown Bethesda

Cozy Oxford Getaway

2 Bedroom Stylish Kingsmill condo

Beach Bungalow on the Boardwalk

Beach Condo Block Off Boardwalk

2 bedroom condo with oceanfront one block away!

Light-filled Private Oasis / Close to Capitol Bldg
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 R515 ZAR per night before taxes and fees

Verified guest reviews
Over 5,720 verified reviews to help you choose

Family-friendly vacation rentals
100 properties offer extra space & 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

Wi-Fi availability
140 of Chesapeake Bay vacation 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!
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