Holiday rentals with outdoor seating in Bridgeport

A unique architectural home built 1955 that’s set on 2 plus acres surrounded by mature hardwoods. Set in a lovely neighborhood. Lots of interesting Art and Literature available to enjoy.I had wanted to stay on several visits but this location wasn’t available. I lucked out for 3 nights and so glad I had the opportunity to. I will definitely book again. Gloria was a responsive host. Instructions were clear and detailed. Lots of closet space in the 3 bedrooms and plenty space, multiple sitting areas. Thank you Gloria.

We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Greg was an excellent host! He answered all of our questions and was very helpful. The house was clean and a perfect fit for our family. The location was also great and easy to walk to town from! Highly recommend and will come back if we find ourselves in Fairfield again.

Beautiful layout and views: The living room extends to an expansive harbor view as we opened the door. When we turn around the lofty A frame transitions into the bedroom connected by a wooden spiral stair. Interior appliances are good and functional. Plenty of Pillows and blankets to get cozy. The Weber Grill is great to use. We used public transport and Uber and it was pretty easy to get around - 15 mins to nearby scenes and restaurants.

We loved Laura and Dana’s Big Easy home by the beach. It was big and comfortable and every detail had been thought about to maximize our enjoyment. Drawers and closets and cabinets were all labeled so we didn’t have to search for anything or guess where anything was. Literally every need had been anticipated! Amazing. The beds and bedding and linens and towels were abundant and soft and comfortable. The kitchen amenities were awesome, from an air fryer, to a full set of bar tools and blender, to great appliances. The decor was happy and cheerful and creative and fun. There were so many places to sit and enjoy, both inside and out. Do not hesitate to choose this wonderful place for a visit of any length. You will love it!

We enjoyed our stay. The place was clean, easy to get to, and had comfortable beds and furniture. Great place to stay near Sacred Heart University.

My family had a great stay at Amanda's place. It was the perfect vacation spot - we really enjoyed the panorama view! Everything was just as described and we felt right at home.

Highly recommend this home! We had 5 adults and is a fantastic spot for a family vacation! Lots to do with access to cedar beach and walking trails as well as a very short ride to a local restaurants! House was spotless and owners were very responsive we had prior and during the trip, checking in to make sure we didn’t have any issues!

You will love this place. omg so beautiful so clean so quite! i can list a bunch of positive words and they will all fit well with Shelley and her place! Thank you so much for the high chair and baby playpen, i appreciate you having that for us to use as an option. If you are looking for a quiet peaceful get away with no hassel Shelley's listing is what you are looking for ! I hope to be back in the future!

I really enjoyed myself on this brief stay and would gladly stay again the next time I’m on Long Island. Everything was positive, from my communication with Edward, to their flexibility when I overslept, to the comfort of the bed. Highly recommended if you’re on Long Island and don’t feel like staying at a hotel.

I love this place. Perfect but what we were looking for. Walking distance to access beach. Overlooking the pier. Very clean and check in with.

Kimberly is such an amazing host; my guest and I enjoyed every moment of our time here. Photos are 100% accurate. --Such a pristine experience, do not hesitate to book with her… you won’t regret it!

We booked this place to be close the the festival downtown and it was. 1.3 miles or 25 minutes walk. Perfect for us. The Airbnb was clean and spacious. Shower is a little small but ok. King bed is very comfortable. Yummy welcome treats on the table was a nice touch. Keurig pods and maker available for your pleasure. Well lit and very secure. Felt safe at all times. Great place to book if you need to stay in this area.

What a beautiful place to stay in the Hudson Valley. The view from the property is just breathtaking. Dan’s place is very clean, open and beautifully furnished. We can’t wait to come back!

We were recently in town to visit family, staying at Traci’s made our visit enjoyable and relaxing. Check-in was easy, the apartment was clean with a comfortable bed and a peaceful view of the brook. Overall, we had a pleasant stay, thank you Traci!

We stayed two nights at Alisa and Lena’s place. The place was just as described, comfy and very quiet. Would definitely recommend it for a visit in the area.

Maricela was very responsive and flexible throughout our stay and booking arrangements. Thank you!!

We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!

We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

Great retreat for a long weekend. Enough space for family of four. Easy access to everything in the Greenport area. Mia was very responsive, and the place was great. We would stay here again!

Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.

We had a great stay! Instructions were clear and the home had everything we needed.

Such a great space and place for a colleague and me on a short one night trip. With a cool fish tank too! Great amenities and very clean. Shy of arrival a garage spot opened and Dave was very helpful in providing that option for a small fee. Easier knowing you have a safe, covered and gated parking spot too! Although the area seemed really safe anyways. Great hospitality.

Had an amazing stay in Greenport. The condo was exactly as listed, extremely clean and has a ton of amenities. Tom communicated from when the reservation was booked until the end, he was readily available, answered quickly and gave tons of informations. The location is ideal with the private beach and pool and a quick 5 minute drive into town. The condo offers a great little kitchen, a wonderful balcony with a water view and an unbeatable sunset and all the amenities you need for your stay. Pool towels are provided, plenty of bathroom towels, there’s a coffee machine, 3 tvs, a variety of dishware and there’s coin operated laundry in the basement. The staff that works the grounds and property are also super friendly. The town of Greenport and other surrounding towns are all close, you have endless options for vineyards in close vicinity and there’s tons of amazing restaurants within a 5-15 minute car ride. I highly recommend booking this property, I will definitely be rebooking! (If yo