Hotels with Parking in Southold

The restaurant was lovely with a nice view of the marina. We had a continental breakfast which was good. The room was spacious and SO clean, nice kitchenette and bath. All in all a nice stay.

The house is beautifully finished, the rooms are spacious and the rain forest shower was awesome. We used the bikes to cycle to the wineries and enjoyed relaxing outside at the firepit in the evening.

Every thing location, convenience, price

We had the most wonderful Mother’s Day weekend here. The service, food, and amenities were excellent, creating a truly peaceful atmosphere. Being by the water, listening to the birds, and sipping on delicious cocktails was simply priceless. We already loved Shelter Island, but staying at The Pridwin made us fall in love with it even more. It’s the perfect spot for a staycation, especially during the quieter off-season like May!

Loved the location. The room was spacious, very clean, and had exactly what we needed. The room in A building had a partial view of the water from the balcony and the pool. The grounds were nice. I liked that there were adirondack chairs to watch the sunset. It was a simple walk down to the sand/beach area.

Location location location... Amazing staff. Other guests became instant friends.

Dry tasteful finishes, newly renovated, rooms very cozy

Relaxing , quiet, comfortable

The property was very clean and well-maintained. The staff were friendly and helpful throughout our stay. The location is perfect—just 5 minutes from a private beach. We really enjoyed the pool and the amazing backyard setup, complete with comfortable seating, a BBQ grill, and a cozy fireplace. It felt very safe and relaxing, making it a perfect getaway spot.

The bed and breakfast is a super homey b&b. Felt like it came out of Gilmore girls or a tv show. It’s an old house with different themed rooms (we stayed in the sea shell room!) and every piece of decor is well thought out and there’s so many small details that add to the experience. Like a makeup wash cloth so we don’t get the white towels dirty, beach towels and a tote for us to use during the trip! And extra pillows and bedding already in the closet. It’s also less than 5 min from the train - you really don’t need a car. A great getaway from manhattan.

Incredibly friendly and accommodating staff. Comfortable bed/bedding.

The bed and pillows were so comfortable. The kitchenette was absolutely brilliant, fresh croissants for breakfast, yoghurt, cereals and fresh fruit also. Coffee & Tea all day and chocolate cookies for afternoon tea! We were also given a beach pack which included chairs, towels and an umbrella!!

Relaxing atmosphere, very interesting place, beautifully decorated.

An absolute gem! Everything was spotless, and you can tell how much care and attention goes into every little detail. Beth is an incredibly kind and welcoming host who made us feel like we were visiting a friend rather than staying at a hotel. The thoughtful extras truly set this place apart: complimentary bikes, beach chairs, hats, and even high-quality organic sunscreen available for guests. The breakfast was delicious, and the whole experience felt personal, comfortable, and relaxing. Can't wait to come back!

Calm and peaceful atmosphere. Convenient location close to the commercial area and north ferry. Kind and attentive host.

Beautiful, very clean and comfortable. Great location.