Bed and breakfast vacation rentals in Southampton

Kathy was welcoming and friendly. The house and grounds were well kept. The room was exceptionally clean, with fresh robes and nice linens. Kathy provided a continental breakfast. This is a very good location for beach and downtown and is quiet. Overall, we had a good experience. Note this is a B&B, so you have a room, but the house including bathroom is shared space with Kathy and other guests.

I seldom use the phrase “home away from home”. However Cathy’s really means it! Thank you Cathy for hosting us and prepared a nice breakfast by yourself! Next time when we are near the area, we’d love to stay at your place again!🌟

Such a wonderful lodging! My son and I stayed for a week for him to attend camp nearby and the hospitality with the entire staff was remarkable! Clean, quiet, communal feel and tended to my every request! I highly recommend this charming little place!

we had such a lovely time at Jayne’s place! The room was very clean, we loved the garden and her cats! It was perfect for a little city getaway! We definitely want to come back:)

John's bed and breakfast / the Candlelight Inn is a wonderful experience. The room was clean, beautifully kept and just as advertised. I would highly recommend this stay and shelter island in general, as there are many beautiful beaches, stores and restaurants all 5-10 minutes away. The final night of our stay ended with our eating dinner on the porch with fireflies and other guests. We even snagged some furniture from the thrift store across the street!

Lovely b&b in a cute town with everything you could want/need. Michael was a great host and the breakfast was delicious. Comfy sleeping arrangements and just all around a lovely experience. Will definitely be back!

What a perfect spot in Shelter Island! Beth and team were amazing - we were visiting one night for a wedding on the island and the ceremony was at 2 PM the day we were arriving. I messaged Beth and she was extremely helpful with providing early check in to ensure we could get ready prior to the event! The actual B&B is beautiful - fantastic design, super clean, cool art and the backyard area with the pool is so dreamy. There is even a little workout area near the pool with a Peloton and a Lululemon mirror. Its a short drive from the North ferry, lots of restaurants and cafes and only a short walk to the beautiful Crescent beach. It is such a serene setting and I truly feel like I am on vacation.The room was beautiful and the bed was comfy, I am OBSESSED with the hand soap and have to find it for myself because it smells SO GOOD! I would 100000% recommend staying here and I will definitely be back!

We had an amazing stay at Jayne's home. She is a very friendly and accommodating host who makes you feel at home. We got a lot of helpful local tips and even got to meet some of her friends one evening. The house packs a lot of history and is an aesthetic work of art, curation and dedication. The garden is equally picturesque and perfect for breakfast and relaxing. We felt the amenities were great too. Fresh breakfast (and a pie!) served in the morning, BBQ grill and firepit for a relaxing night to stay in, and bicycles for exploring the town and beaches all made our stay very convenient and seamless. Thanks!

Thank you so much for sharing your lovely home with us! We had the best time and will definitely be back! Thank you!

What a treat! I grew up in Madison and didn’t realize this amazing bed and breakfast was right under my nose! Michael was incredibly friendly and helpful and the space was fantastic. I will absolutely be coming back and highly recommend it to anyone looking for a beautiful space, central location and delicious breakfast!

My friend and I came for a baby shower weekend. It was absolutely my best experience with any Bed and Breakfast/Air bnb ever! She could not have made us more comfortable and at home. Her garden is absolutely incredible- I could not stop taking pictures of every corner! Even inside her home is full of antiques with a story behind each one! I cannot wait to have another girls weekend here. It is also perfectly located to walk right into town!

Absolutely loved staying at the Oceanview Terrace this Easter weekend! Adriana and Yanni were fabulous, very friendly and responsive. The location was great, loved the cottage I was on, overlooking the Shinnecock Bay. Minutes outside of Southampton and other great local restaurants and shops. Very clean and I slept like a baby in the beautiful King bed with fresh linens with the best pillows lol!! I will definitely be back and recommend to all my friends & families.

Danny’s resort is an absolute gem and Danny is an absolute pleasure! The bedroom and private bathroom are a great space, the bed is very comfortable, the back deck and poolside are beautiful, serene and secluded, the breakfast is fresh and filling, great BBQ and Danny and his dogs’ company was lovely 😊! Danny had so many recommendations on things to see and do which we wouldn’t have managed to see or do without his friendly chats throughout our stay and the bits of advice to avoid traffic was massively helpful! I would highly recommend Danny’s resort and looking forward to the opportunity to stay again! Thanks again for a lovely stay Danny, Milo and Little Max!

Fantastic value and location!

We enjoyed a wonderful stay at Johnny & Mark’s beautiful home! Conveniently nestled among several wineries, many within walking distance, this incredible Bed & Breakfast is perfect for your North Fork getaway! Johnny and Mark are welcoming, accommodating, and gracious hosts. We hope to return soon!

This space is in a lovely B&B a few minutes from cute shopping and eating in Old Saybrook. I've stayed here twice and loved it! The fabulous: - Spotless space. - Sophisticated decor. - Super comfortable bed. - Smaller rooms but laid out very well with sitting areas and high ceilings so it feels quite spacious. - Divine shower with great water pressure. - Extremely communicative, kind, and helpful property manager! - Fabulous French bakery and restaurant downstairs. (!) - Outdoor sitting area. Things to be aware of: - The stairs to the bedrooms are very steep and narrow— not appropriate for people with mobility issues. - The breakfast is a credit for a place down the street- this made timing a little complicated. - You might want to bring an eye mask as it's quite bright in the morning. - There is a beautiful church across the street, but the bells chime pretty late and pretty early so if you're a light sleeper, bring earplugs. Overall, highly recommend!

One of the best kept secrets in the Hamptons. Picturesque water view setting yet convenient to all the hamlets and village attractions . Monika is a fantastic host!

Such a beautiful stay - Monika’s b&b is the perfect getaway and in an amazing location. Gorgeous and peaceful property which is also so quick and easy to get into the towns Bridgehampton / Southampton. The room was big, bright and absolutely spotless with windows full of leafy green trees. We can’t wait to come back.

This place is definitely a must go to, the rooms are beautiful! The whole place is spotless and super clean. Adriana is amazing!! I had just moved from Florida and needed a nights rest before continuing my trip, she was so helpful and kind Thank you for all you do and did Adriana Highly Recommend, and I will definitely be back!