Holiday rentals with outdoor seating in Maryland Beach

Our family has a beach house in Ocean Pines, and we are looking to purchase our own in the coming years. We have stayed in all parts of ocean Pines and love it so much, we came across this house a couple months ago and I’m so glad we did! We spend most of the summer in Ocean Pines had different rentals and will definitely be coming back specifically to this one!! it’s perfect for our small family and pet friendly! The house was small but spacious, quiet and tranquil. 10/10 highly recommend!

Hall’s Cottage is one of the last places hanging on to the charm of yesteryear in Fenwick Island. It’s great seeing all of the beautiful new homes in Fenwick as you walk the streets, but it was really cool seeing my 10 and 8 year old love the cottage so much. It was perfect for a small active family. Marlene’s instructions were simple and easy to follow and she was a great host. We are looking forward to coming back in August for more fun and relaxation!!!

This is our fourth stay at the beach shack and as always, it was a true 5-star affair. Jennifer’s sense of design is impeccable—you will feel at home and in a constant state of chill staying here. Super serene with the bay just outside the sunroom, ultra quiet neighborhood and super comfortable furniture. Jennifer is the best communicator, reminding you pre trip, during trip and even post trip how much she values her role as a host, and YOU as her guest. Can’t wait to return this winter for a pre new years getaway, and another fun summer stay in 2026!

Cozy little beach spot. Shelly was so responsive and helpful! Would highly recommend!

Let's see...if Martha Stewart had a rental cottage, it would look just like Lisa and Jay's carriage house. Everything from the splendid charcuterie board and Prosecco on ice that awaited us upon our arrival to the beautifully designed cottage and wonderful gardens helped create an amazing vacation that we will not forget anytime soon. Jay and Lisa truly paid attention to every detail right down to the perfectly placed English antiques, fresh cut flowers and towels so thick you could drown in them. Nothing was missing and their hospitality made you feel right at home. We had smiles on our face the entire time! This is now my new Happy place. The gold standard by which every rental will be judged....perfect hosts, perfect place..like I said...Martha Stewart. Thank you Lisa and Jay for making our stay a wonderful experience!! We will definitely be back to your Lewes Carriage House whenever possible!

Janice’s house was lovely! Great location. It looks just like the pictures. The view from the living room and back deck is stunning. The house was very tidy. Janice communicated well and promptly. The only disappointment was that there is no screen door in the master bedroom, and therefore, I couldn’t enjoy leaving the sliding doors open, which I love to do when staying in a waterfront home. Otherwise, we had a wonderful stay! Would definitely recommend!

Jennifer’s place was the perfect home away from home. About 15-20 mins away from the boardwalk but still in a great part of Ocean City. I would definitely stay again.

A beautiful home in an amazing location. Loved the peaceful and friendly neighborhood and easy beach access. Natalie was super communicative and friendly. She shared clear instructions and great recommendations for things to do nearby.

Super happy with our stay here. On the quieter side of Ocean City and right next to the beach. It had everything I needed: easy beach access, perfect location, quiet neighborhood. The bed was very comfortable as well. Even had a Brita filter in the fridge, so I didn't have to go buy water bottles.

Even though we had to leave early the stay was perfect. Ashley was always very responsive anytime I had a question and the condo was just as described

Identical to pictures! Beautiful rental in convenient location. The beach and boardwalk were easily walkable and having Fish Tales next door was convenient! My only suggestion would be is to bring an eye mask if you are a light sleeper, there are no shades on kitchen windows so it’s very bright in the early morning since it’s all connected. It helped us to get up and moving in the morning so we didn’t mind. Morgan was quick to reply to messages and a very gracious owner! We will definitely be back.

We had a great stay. Place delivered (and exceeded) our expectations and hosts were responsive throughout our experience. Great location and place for getaway with friends.

This was our second summer in a row staying at this lovely Airbnb! Cannot recommend it enough. Great space, has everything you need for a beach vacation…including the perfect location! Walkable to the boardwalk and right next to a great bike path for walking/running/biking around.

I loved Mihaela’s place. It was beautiful. Very clean & smelled SOOO good when we arrived. We did have an issue finding the right building at first, but after re-visiting the message from the host, we were easily redirected. The space felt at-home. Host was very responsive & communication was very clear. Unit looked like pictures. Perfect space for what we needed. the bathroom in the bigger bedroom was a little small, but that’s honestly extremely minor. I would most definitely stay here again.

I stayed with 3 children and we had a wonderful stay! The house was very clean, comfortable, and looked exactly like the pictures. There were no complications at all during our stay. The host was easy to communicate with and extremely responsive to any questions we had. Everything was smooth from check-in to check-out. Highly recommend and we’ll definitely be back next year for our annual family stay. Ira was great 😃

Had a great weekend and this place was perfect, It felt like home while on vacation! Beth and Andrew were quick to respond and were GREAT hosts :) will definitely be staying again in the near future! Thank you so much for letting me enjoy your gorgeous place with amazing views !!

This is the second year we stayed at this beautiful condo! Views of both ocean and the bay are spectacular!! Condo was clean and easy to access. Love the pool and beach! Close to great restaurants!! Margaret is a fantastic host!! Highly recommend this condo! We will definitely be back next year ❤️

Great location, loved the views. Host communicated very well, and property was as advertised.

I will book Heather’s place again! Why? Simple…the ocean view…the simple and beautiful decor…the place was SO clean and so fresh and so beautiful…it had all that we needed as full on beach goers with a required place for showers and sleep. The street was so amazing and so cozy…coffee pot for mornings…fans and AC for a lovely cold sleep…steps to whatever we needed…just true basic beach needs. Loved it! Will definitely stay again in the future…and, Heather…so responsive! Highly recommend!!

We had a great stay at Colleen's place. It was exactly as pictured and Colleen was a very responsive host. It had everything we needed during our stay. We were traveling with a 2.5 year old and an infant and were very comfortable. The pool and close proximity to the beach were a big hit. The air-conditioner in the bedroom is a bit loud, and could be disruptful to some, fortunately our daughter didn't mind. The queen pull out sofa was also very comfortable to sleep on. Overall would recommend!

Shiri's place was perfect. My wife and I have both frequented OC since we were kids, and we both agreed that this was the nicest place we have ever stayed. Far enough from the boardwalk to be peaceful, close enough to travel to the boardwalk if we wanted. The condo was clean, there is a washer and dryer in the unit which is a plus, and a tv in both the living room and bedroom, which is something we always look for. There is plenty to do in the area! Unfortunately, it rained during our whole stay, but you have beach access just outside of the building! We are excited to stay at Shiri's place again (hopefully when it's not raining 😂) and spend some time on the beach! We sat on the balcony every morning and night and it was so peaceful. Shiri was always very helpful and kind - she is such a wonderful host!

The place is awesome. Great views great location. Perfect get away we will be coming back for sure 👍

Had a wonderful time. It was right next to the beach. The included amenities were very helpful and thoughtful. We had a wonderful time and would recommend to anyone interested in a great OCMD stay.

Wondering place we stayed at! Clean room, with some modern furniture. This room has everything we needed. Definitely will come back.