
Condo vacation rentals in Chesapeake Bay
Find and book unique condos on Airbnb
Top-rated condo rentals in Chesapeake Bay
Guests agree: these condos are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake Bay condo rentals
Weekly condo rentals

Across beach condo weekly rental
The property at the Baronet is well located - right across the street from the beach but also walkable to much of the incredible town of Cape May. Michael is a generous and responsive host.

Wight Bay Unit 245
Jenna’s place is great, very clean and spacious. And a super relaxing space, I highly recommend it

Spacious Direct Oceanfront 1BR Condo w/Balconies
An amazing place! Double balconies for sunrise and sunset views. Very peaceful and friendly neighbors. Everything within walking distance. Would highly recommend! Natasha was very quick to respond to any questions or needs you may have.

Beautiful Beach-View Condo
Everything was great. Wonderful location, great amenities, clean and beautiful view. Hosts were very responsive. We would definitely come back.

Cozy oceanfront condo with stunning ocean views
The condo was wonderful! It was quiet, peaceful, extremely clean and overall the best place when you want to get away and have a peace of mind. They have good stores to shop at and good restaurants to eat at in the surrounding area. It was just a wonderful experience for me to be there and I will definitely be returning!

1st Floor 3 BR Condo close to Beach with Pool!
Mike’s beach house is perfect for a family or group trip. More than enough space to fit everyone and the location is amazing. You’re less than a 5min walk to the beach but also return to a quiet dock rental. It was so calm sitting on the porch each morning looking at the water. Far enough from the hustle and bustle but close enough to enjoy the boardwalk and attractions when wanted. He’s super communicative as well. Would definitely stay again.

Mid-Town OC! Ocean Block... Steps to the Beach!
Michele's home was very nice! It was comfortable for our family of five, clean, and well-organized. We simply loved it! 🤗 I would like to go back on summertime .

Modern 2BR/2BA – Beach Pass + Bikes, 5 Min Drive
We really enjoyed our stay. Jonathan provided great guidance regarding how to easily travel to this condo and getting access to the unit was seamless. The development is beautiful--great walking neighborhood and beautifully landscaped. The location enables you to access all the great things about Rehoboth and you are within walking, biking, and a short driving distance of everything. Jonathan's property is pristine and welcoming. We felt right at home immediately and were able to truly relax while we were there. Everything you think you're going to need is there and we really appreciated that core supplies were on hand when we arrived.
Pet-friendly condo rentals

Luxury water-view condo with high-end finishes
Linda’s condo was unmatched! Her attention to detail and cleanliness is amazing. I’ve stayed at many places like this before, as this is our families preferred way to travel. This is by far one of the best condos we’ve ever stayed in. It was very organized, there were additional items ( such as paper products, spices) available to use. There were even little hospitality baskets in each bathroom with eye masks, mints, Q-tips. What a nice touch! Another reason we chose this condo is the storage shed with beach toys and chairs. It was so lovely to walk to the beach or sit near the bay. Now that I told you how great the condo is- let’s talk about location! One block to the ocean and on the bay. We walked or rode bikes everywhere. I really enjoyed being there on the “off season”- the weather was 70+ and sunny every day. This vacation was a 10!

Bright, large zen studio on historic Logan Circle
A great stay! I felt right at home at Bens place and there were grocery stores and good restaurants nearby. It was also a quick 14 minute walk to the Walter Washington Convention Center. Overall, a super comfortable space with everything you'd need for a DC stay in a trendy neighborhood. I highly recommend.

Walk to beach large 2/2 in "Kingsmill on James"
Gayle’s place was a great location to stay at with our dog!!! Great neighborhood to walk him in and the marina/beach is an added bonus! Gayle was very communicative and check in was easy. The space of the condo was great for a family and large dog! We will definitely be staying again!

Brand New Reno in Historic Dist w 2 Parking spots
Comfortable is the word to describe this place. Cute, cozy, clean with great walkability. Megan’s instructions were clear, easy and she was more than very responsive. We meandered through galleries, coffee shops and local restaurants. The Navel Academy tour was outstanding. The weather got in the way of our boat cruise. Plenty to see and do with great recommendations from our Airbnb host. Thank you Megan for a great weekend!

Remodeled Cape May condo -with private backyard!
I also had to mention that the bed was terrific - it was a very comfortable king, and getting into it each night felt like the perfect end to a vacation day. The apartment was very clean, and there was a very clever use of space. Kristen was helpful and welcoming, and this was a great hideaway for two in Cape May. 😁

Beach Perfect Getaway: 2-Bedroom Apartment
This condo is very clean and nicely equipped. We had no problems, locating it and certainly felt safe and had no problems. There is a diner right next to it which is within walkable distance. The beach and Boardwalk are about a 10 minute drive with traffic. A walk to these areas would be relatively long but you could potentially ride a bike. Certainly would stay here again.

Elegant 3-Bedroom Condo in Lewes with Pond Views
Very nice place with enclosed patios. Neighbors were very friendly.

Sweet getaway - beach block, steps from the beach!
Loved this small Airbnb….only steps from the beach. Everything was clean and perfectly placed. Loved how detailed everything was described. Definitely will be going back. (A side note - the blinds are a perfect touch….for privacy and yet allows the light to come in. I’ve never seen these kind of blinds before. 😊) Thank you and God bless!
Condo rentals with a pool

Ocean View, Large Condo, Heated Pool
We had a great stay at Valerie’s condo, it was a great space for our group of 6 and had everything we needed. Valerie was very responsive for any questions we had!

Bayside Boaters' Paradise | Pool | Family Fun
Beautiful view on the bay. Ally was very thorough & communicative throughout the process. Only thing that is kind of a bummer is that linens are not included. But other than that, I highly recommend Ally's condo.

Waterfront Condo With Olympic size swimming pool
James was an amazing host. He was responsive, helpful, and kind. The condo was beautiful, clean, and perfect for our family. The neighbors were also very kind and welcoming. My children loved the pool and walking the bay. The views were second to none and the location was perfect since it was minutes away from restaurants, stores, and Bethany beach. We will definitely be booking again!

Condo with Pool in the Heart of OC
Stayed at this condo for Oceans Calling—which was about 3 miles away. It was tidy and welcoming and fit our needs well.

Ocean View Condo W/ Indoor and Outdoor Pool
Awesome place and great location for all OC activities!

Bayfront Condo 46th St *2 POOLS*Free Linens/Towels
I can’t say enough how beautiful this condo is! It was absolutely spotless and the views are worth every penny! Felt right at home!

Cozy Condo
We really enjoyed our stay at the condo! Maria was helpful and responsive. All amenities were as described. We’d we happy to stay at this location again.

Time N Tide Condo - 2 BR w/Pool, Boardwalk/Beach
The Time-n-Tide condo was great! Very well furnished, great decor, excellent amenities and great location. We felt very relaxed and comfortable during our stay, super cozy. Tina & Daryl we're very helpful with information and responsive to any questions we had. We hope to stay here again - great choice and value.
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