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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Superhost

Condo in Ocean City

4.76 out of 5 average rating, 192 reviews

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

Newly renovated and beautifully decorated direct oceanfront condo 1BR/1BA on the 4th floor, 12th St. on the center of the Boardwalk. Enjoy AMAZING VIEWS of the sunrises over the ocean and refreshing ocean breeze from the top floor. You can watch Ocean City’s best access to entertainment like the air show, fireworks, car shows and more on your private balcony. Within walking distance are great restaurants, shopping, nightlife, amusement parks, and plenty of water activities, and Pet Friendly.

Guest favorite

Condo in Ocean City

4.94 out of 5 average rating, 176 reviews

Modern Oceanside 42nd st 2bed 2bath sleeper sofa

Gorgeous 2 bed, 2 bath 1st floor condo is on 42nd st. Ocean side! Newly renovated, modern and clean condo sleeps 8 (air mattress for 2)has everything you need to feel like you’re at home away from home! Beautifully decorated and complete with stainless steel appliances, fully equipped kitchen, WiFi, a color changing gas fireplace, 80” tv, and is furnished with linens and towels. Just steps to the beach, convention canter and walking distance to the bars such as Seacrets, Coconuts and Taphouse.

Guest favorite

Condo in Rehoboth Beach

4.9 out of 5 average rating, 155 reviews

Modern Dog Friendly Condo

LOCATION. Cute, clean, and modern 2 bedroom 2 full bath condo located on the second floor perfectly located to so much of what Rehoboth has to offer! Rehoboth boardwalk is 3.6 miles away. The rehoboth/Lewes bike trail is walking distance from the unit. Downtown Lewes is 3.3 miles away. 4.8 miles to Dewey Beach. Everything is a 5-10 minute uber. With other local restaurants in walking distance, and a wawa steps away! You honestly can’t beat the convenience of this great cozy beach condo!

Guest favorite

Condo in Rehoboth Beach

4.82 out of 5 average rating, 372 reviews

2 Bedroom Condo Rehoboth Beach w/ No Chores

2 Bedrooms Condo. Great for families or couples. Walking distance to restaurants, beach, bars & other entertainment. Driving distance to 5 different golf courses within 15 minutes. Walking distance to water park & amusement park. Pool on site. Bike & running trail behind the condo. Roku on every TV with Xfinity app for local TV & a Spectrum app for premium channels. We have MGM +& you can add any of your own streaming services during your stay. Smoking area on deck. No chores for you to do!

Guest favorite

Condo in Ocean City

4.87 out of 5 average rating, 71 reviews

UNIQUE Bay Front Sanctuary Condo

Gorgeous upscale Bay Front Condo - This is your quiet, secure patrolled dream vacation. You will have a spacious one bedroom, one bath open-concept condo that can sleep 4. Watch the magnificent sunsets from your dining room or private balcony on the beautiful Bay. Fish right from your pier, bring your kayak or enjoy the views from the lovely picnic area. Walk across the street to the famous Ocean City Boardwalk and beach. Enjoy parasailing or jetski without even getting into your car!!

Guest favorite

Condo in Ocean City

4.84 out of 5 average rating, 108 reviews

GREAT LOCATION~Steps to Beach, Bath/Bed Linens Inc

BEST LOCATION~STEPS TO BEACH~All Amenities ...Your Own Personal Space..Included: BED LINENS & BATH TOWELS INCLUDED, ALL BEDS WILL BE MADE UP WITH FRESH SHEETS AND 6 SETS OF TOWELS: EACH SET TO INCLUDE A BATH TOWEL, HAND TOWEL AND WASH CLOTH. Steps to the BEACH & the BAY, Outdoor Shower. Walking Distance to Restaurants, Bars, Grocery, Carry-Outs, Brick Oven Pizza,Convention Center, Boardwalk Tram, Mini Golf, Amusement Park, Bike Rental, Everything! Watch Sunrise & Sunset from Big Balcony!

Top guest favorite

Condo in Rehoboth Beach

4.96 out of 5 average rating, 160 reviews

Classy Beach Getaway

Our condo is close to everything: Outlet shopping, Entertainment (water park), Biking trails, A pool and jacuzzi on the property, Downtown shopping, some of the best restaurants in Delaware, great views, art and cultural activities. You’ll love it because of the new and IMMACULATE decor, the overall ambiance and the location! It's great for couples, girlfriend getaways, business travelers, and families with older kids :). PLEASE NOTE, during the summer season we only book full weeks.

Guest favorite

Condo in Ocean City

4.89 out of 5 average rating, 115 reviews

Perfect location!

This charming 2-bedroom condo is perfectly located in Ocean City to take full advantage of the beach lifestyle. Imagine relaxing on your covered outdoor balcony, enjoying warm and breezy weather while taking in the sights--including being able to see the bay. You'll be a quick walk to the Boardwalk and all major downtown locations. The interior is beautifully-maintained with loads of character, including laminate flooring and custom wainscotin. Available for all Ocean City events....

Top guest favorite

Condo in Ocean City

4.87 out of 5 average rating, 102 reviews

Charming Remodeled 2 level condo w/ amazing views

Beautifully remodeled condo situated 2 blocks from the Northside Park and 2 blocks from the ocean, you have plenty of options for recreation & fun all year long. This 3rd floor unit features 2 level living w/ kitchen, living room, den with (sofa/bed), full bath on the main level and 2 bdrms plus 1 full bath on 2nd level. Enjoy canal views from 1 of 2 outdoor decks. New shopping center just completed with plenty of dining options, coffee shop, juice shack, surf shop and much more.

Guest favorite

Condo in Dewey Beach

4.84 out of 5 average rating, 193 reviews

On the Bay, Private Beach-Boat Slip

Enjoy your own piece of paradise! Walk out the door 10 steps to the water! Modern condo located on the bay with great views, a patio, a grill, a private beach, boat slip, and 2 blocks to the ocean. Perfect for couples and small families! This is a well-appointed 500 sqft open concept condo with 1 bedroom, office & 1 bath. We take great pride in our condo and keep everything updated. New living room furniture Spring 2021. Completely renovated in mid 2020.

Guest favorite

Condo in Ocean City

4.89 out of 5 average rating, 131 reviews

Water Front Condo w/Pool Short Walk to Beach

FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!

Superhost

Condo in Ocean City

4.88 out of 5 average rating, 211 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!

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What guests are saying

Mid OC Bayside Canal Condo Remodeled-Pets Welcome!

5 out of 5 average rating, 24 reviews6 months ago

Condo is beautiful and is just as described. Check in was very easy and with Kathy’s clear instructions we were able to find it right away. Parking spot in front of the condo was big plus too. Very calm neighborhood, you could only hear birds in the morning while drinking coffee on the patio. We loved it, our dogs did too. Thank you Kathy. We will be back!

Condo in Ocean City

What guests are saying

Lovely 2BR Condo - Rehoboth/ Dewey

4.98 out of 5 average rating, 83 reviews7 months ago

Michelle's place was spacious and well-appointed for myself and four other people. The water pressure was great, there was plenty of hot water for showers, and it was conveniently located. The neighborhood was quiet, and while we didn't have time to enjoy the amenities, the screened-in porch was lovely to enjoy and, best of all, free! The beds were firm and comfortable; the apartment was very clean! Thanks for a great stay, Michele!

Condo in Rehoboth Beach

What guests are saying

Sunset Tranquility - 3/2.5 Midtown-1 block Ocean

4.89 out of 5 average rating, 27 reviews8 months ago

We loved this place! beautiful unit with a Bay View, pool on the roof top, 2 parking spots and walking distance to everything. Violet was very responsive and showed that she cared if we got to the place safely and gave clear instructions on how to get into the space. we will be back, thank you!

Condo in Ocean City

What guests are saying

Oceanfront gorgeous condo. Fountainhead.

4.63 out of 5 average rating, 32 reviews8 months ago

This was the perfect spot for our beach vacation and hit all the marks we were looking for. Super clean, thoughtfully stocked. With a small child and our elderly parents, it was nice to have such close access to the pool and beach but also, have a perfect balcony view of both. Elevators and a well-maintained boardwalk through the dunes a super plus for the grandparents (and our beach buggy). We were pleasantly surprised to catch a fireworks show from the bayside balcony as well! What a treat this balcony is! In addition to the fireworks, it was amazing to see both the sunrise and sunset from the privacy of our own condo. The hosts were super responsive and accommodating. We will be back.

Condo in Ocean City

What guests are saying

2BR/2BA/ 5 Bed condo with 2 private balconies!

4.93 out of 5 average rating, 44 reviews6 months ago

Another great stay. The location can't be any better, central OC at it's best. Easy walk to the beach. We tried Barrio Taco this time, it's huge, recently remodeled. Dead Freddie's across the street is a plus. Plenty of room for our family. We'll be back! Raif went above and beyond with his hospitality - thank you.

Condo in Ocean City

What guests are saying

Lovely Large Bayfront!

4.85 out of 5 average rating, 46 reviews9 months ago

Amazing view from the deck and living room of the bay - we spent quite a lot of time just watching nature outside. Beach entrance was right across the street, walkable and near great restaurants and boutiques. Unfortunately, we missed the linens/towels info in the listing but Steve was able to recommend a local company to bring those items to us. We also enjoyed the rooftop pool that was part of the building while not at the beach. If you are looking for a centrally located rental in Ocean City we would highly recommend this property!

Condo in Ocean City

What guests are saying

Ful Dek - Family Casual Condo-Midtown-Ocean Block!

4.85 out of 5 average rating, 55 reviews9 months ago

Really have no complaints about Jen’s place!!! There is so much space, it’s very cozy and homie. TVs in every room. The deck is so cute to sit outside and play some games or eat breaker/dinner. You have two parking spots, access to the beach and many restaurants around you. The bus stop to take you to the boardwalk is not a far walk either so you have unlimited access to everything you need. This was my first time back to OC MD in a long time and Jen’s place was the right place. 10/10 and will hopefully be staying again soon 😁

Condo in Ocean City