
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.

Newly Renovated 1BR Condo Sleeps 4 - Unit 4
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 in private lot, in-unit Washer/Dryer, Full Kitchen. Steps away from public transit buses that route to multiple Orange/Blue/Silver line Metro trains. Comfortably accommodates the traveling professional, those on vacation and is even 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.

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!

Water view at Ocean Pines Yacht Club Condo
Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

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.

A bit of Paradise
Charming end unit secluded in the heart of Lewes. Shady sitting area for viewing the waterfowl & enjoying the peace & quiet. Lewes marina is across the street so is Quest where can rent Kayaks etc. Over the bridge you will enjoy the historic district, town shops, eateries, food market; kiddy park, canal front park; trolley into Rehoboth Beach Henlopen State Park 1 mile; surfing, fishing & nature trails; Bay Beach 1/4 mile w Walk to everything We offer a %15 discount for 7 days or more

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..

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.

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).

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.

Cozy Old Town Apartment
Welcome to our charming condo in the heart of historic Old Town Alexandria! Enjoy a fully equipped kitchen, cozy living room with a 55” smart TV, and a peaceful master bedroom with en-suite bathroom. With two private entrances, dedicated parking, and easy access to King Street’s dining, shopping, and metro, this home offers comfort and convenience. Perfect for relaxing after exploring D.C., or enjoying the charm of Old Town on foot!
Popular amenities for condo rentals near Chesapeake Bay
Weekly condo rentals

Funky Uptown Apt meets Downtown - Hist District

Beach Sunrise: Walk to Downtown & Lewes Beach

Coastal Modern Condo • Balcony, 2 Baths, East Rt 1

Beautiful Updated Condo Waterfront, Pool, Sunsets

Best Value Condo in Downtown Norfolk

Anchors Away

Bayside Retreat in the Heart of Ocean City!

CANAL FRONT Wi-Fi, Roku, Netflix, boatslip, pool
Pet-friendly condo rentals

Sojourn in DuPont Circle: Modern Meets Historic

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

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

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

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

Cozy Condo 2BR/2BA close to Outlets & Beaches

Bright, large zen studio on historic Logan Circle

Walk to beach lovely 2/2 in "Kingsmill on James"
Condo rentals with a pool

Captains Quarters | Waterfront & Pool

Villa Del Sol, Beautiful stay near beaches/outlets

2BR Coastal Escape with Pool Near Rehoboth Beach

Right on Silver Lake walk to the beach and town!

Beach Escape Condo w/ Pool - Lewes Beach 3.5 Miles

Stress-Free Family Beach Stay | Pool + Kid Perks

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool

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

Beach Bungalow on the Boardwalk

The Loft at Lakeside

Your Hideaway awaits/1-bedroom downtown pad.

2BR Coastal Retreat Walk to Beach & Downtown Lewes

The Drinking Gourd: Stunning Cambridge Penthouse

The Solomons Sunrise Suite

Beach Haven Hideaway ~ stunning water views!

Bayfront Boardwalk Condo w/ Sunrise Views
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 $14 AUD 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, Wi-Fi 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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- Condo rentals United States
- Chincoteague Island
- Virginia Beach Oceanfront
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- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
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- Old Dominion University
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