Condo vacation rentals in Chesapeake Bay

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Top-rated condo rentals in Chesapeake Bay

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Ocean City

4.91 out of 5 average rating, 287 reviews

Ocean Front 802 Midtown Oasis Pool & Parking

Wake up to the ocean sunrise in this modern 2 bedroom, completely renovated, condo. Prime location on 29th street, 2 blocks north of the famous OC Boardwalk, 2 blocks east of OC's premier amusement and water park along with two famous crab house and other restaurants within walking distance. One hassle free off street parking spot, free WIFI, full size washer & dryer, and a beautiful outdoor pool steps from the beach. Enjoy the bay sun set view out the front door and fall asleep to the waves.

Guest favorite

Condo in Ocean City

4.96 out of 5 average rating, 141 reviews

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

OCEAN VIEW and STEPS to the BEACH... Newly remodeled in 2023! 2 bed/2 bath condo with ocean & bay views is located in desirable mid-town Ocean City. Walk to dining, shopping, convention center, amusements & nightlife. Be in the middle of everything, but still have a quiet place to relax. **Summer Months - check-ins on Mon & Fri ONLY Memorial Day to Labor Day. Book Weeks or Mini-weeks. (Weeks: Fri - Fri OR Mon - Mon) (Mini-Weeks: Mon to Fri OR Fri to Mon). *Other months check-in any night

Guest favorite

Condo in Rehoboth Beach

4.96 out of 5 average rating, 112 reviews

Sunrise Studio - Ocean Front Boardwalk Sanctuary

Our quiet ocean front studio has all the comforts of home with amazing views, a balcony hovering over a serene stretch of the Boardwalk, and is just steps away from restaurants, shops, arcades, rides and all of the best boardwalk foods! Walkable to everywhere in town! If you want to venture out further, a bike rental shop is just a few doors away! Enjoy a bike ride through town or to Dewey Beach. If you are looking for a scenic ride, enjoy the bike trails to Cape Henlopen State Park and Lewes.

Guest favorite

Condo in Ocean Pines

4.97 out of 5 average rating, 145 reviews

Escape by the Bay

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

Guest favorite

Condo in Ocean City

4.99 out of 5 average rating, 137 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.

Guest favorite

Condo in Virginia Beach

4.88 out of 5 average rating, 175 reviews

Oceanfront Jewel VB Studio Mesmerizing Ocean View

Newly remodeled, stunning panoramic oceanfront views from the 3rd floor at the peaceful north end of Va Beach boardwalk. Perfect for two, this cozy 355 sq ft studio with wireless internet, large screen TV and full kitchen, has a community pool, back patio, charming beach lawn with tables & lounge chairs and is walking distance to outstanding restaurants, attractions and shopping. Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

Guest favorite

Condo in Dewey Beach

4.98 out of 5 average rating, 180 reviews

DeweyBeach 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.

Guest favorite

Condo in Fredericksburg

4.95 out of 5 average rating, 203 reviews

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.

Superhost

Condo in Ocean City

4.85 out of 5 average rating, 182 reviews

Beachfront 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 a breathtaking view of the beach and ocean.

Guest favorite

Condo in Lewes

4.99 out of 5 average rating, 279 reviews

WALK & BIKE * Culinary Coast * 2 FREE BIKES

Explore Lewes (loo-iss) from our walkable in-town spot. ✔ 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 - includes free YouTube TV with cable channels ✔ Parking is plentiful *Bonus* Two complimentary bicycles provided

Guest favorite

Condo in Virginia Beach

4.95 out of 5 average rating, 100 reviews

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family

Guest favorite

Condo in Ocean City

4.88 out of 5 average rating, 203 reviews

Bayside Retreat in the Heart of Ocean City!

Newly renovated condo!! -Water view. Watch the boat traffic. -Oversized balcony with comfortable seating. -Comfy LoveSac couch. -Walk to boardwalk or beach - 15 minutes. -Walk to Jolly Roger amusement park. -Fish off community dock down below unit. -Close to dining and shopping. -Kitchenette for cooking meals. -Fast Wifi and Streaming TVs. -Fully Stocked Home. Clean linens, towels, toilet paper, paper towels & more!