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Home Vacation This Hotel in Shelter Island Was the Perfect Stress-Free Getaway

This Hotel in Shelter Island Was the Perfect Stress-Free Getaway

by Staff

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I cannot be bothered to think up an entire trip’s worth of itinerary ideas—the mental load is simply too much. So when I went on a little getaway to Shelter Island with my husband and baby this past summer, we were thrilled to head to a spot that had just about everything we could ever want to do right on the property. Including, but not limited to: sipping craft cocktails next to an aesthetically pleasing bookshelf, eating sumptuous meals overlooking the water, taking a sunset cruise in Shelter Island Sound, feeding chickens en route to a competitive family pickleball match, and just serenely taking in the peaceful views.

Yeah, The Pridwin Hotel & Cottages was basically the exact type of don’t-need-to-lift-a-finger situation I needed. And you should probably hear about it if you’re anything like me. Here are the deets:

a building on a dock

The Pridwin


  • Name: The Pridwin Hotel & Cottages

  • Location: Shelter Island, New York (close to the Hamptons)

  • Cost Per Night: Starting at $471

  • Best For: A low-key summer getaway, water activities

  • While You’re Here, Visit: Mashomack Preserve, protected coastal land that’s perfect for hiking, and any of the nearby beaches

  • One-Word Vibe Check: Aesthetic

  • Most Iconic Photo Spot: The lawn overlooking Shelter Island Sound, or the dozens of cute, curated bookshelves and nooks throughout the main hotel

  • Don’t Leave Without: A kayak outing along the shoreline



In order to get to Shelter Island, you need to take a ferry. This was my first time driving a car onto one, and let me tell you, that was actually fun! It really helped me (and my whole family, who tagged along for this trip) feel like we were breaking off from reality for a true stress-free weekend.

Driving up to The Pridwin, the first thing you notice is the immaculate lawn, set up with chic seating arrangements, and the stately white-and-green main hotel, established in 1927. The hotel grounds are expansive and oriented around a ton of fun activities you can do while you stay, including tennis (and pickleball) courts, a chicken coop (you can feed them, it was adorable), a beach lined with chaise lounges, docks set up with kayaks and paddle boards, and an outdoor amphitheater that would make for a great event space.

a living room with a couch and chairsa living room with a couch and chairs

The Pridwin

The outdoor setup was awesome, but everywhere we went inside the main hotel—like the restaurant, spa, and our cottage room—was decorated to a T, with aesthetic choices that honestly made every picture and video angle look like a curated set. Think: elevated, playful country estate with nods to the water. My eyes were very happy.

a room with a couch and a lampa room with a couch and a lamp

The Pridwin

As a fashion director, I have to say I also appreciated the hotel’s swag, including their intage-looking sweatshirts and preppy baseball caps. I even bought my son a little golf tee, because it was too cute to pass up!


We stayed in one of the hotel’s cottages, which was perfect for people (hi, us) who brought a baby and didn’t want to have to worry about him waking up the neighbors with his crying in the morning. Our place had a roomy bedroom with a king bed, a sweet living room/bar space complete with a fireplace, and a huge bathroom with a gigantic shower, double vanity, and a separate room for the toilet. The living room area opened up to a lovely balcony that overlooked the beach and water. We felt super at home with all the space we had while we were there.

a house with a tree in the fronta house with a tree in the front

The Pridwin

For anyone who travels with a baby, we also loved that The Pridwin provided him with a true crib, as opposed to the collapsable play yards that are standard for a lot of other hotels. This made us feel like our little guy was just as much a consideration to everyone there as any adult, which was just plain nice.


Like I mentioned, the hotel grounds have a ton to offer, including a swimming pool, outdoor amphitheater, chicken coop, and tennis and pickleball courts. There’s also a beach with lounge chairs for swimming in the sound, as well as a dock, where you can find equipment for paddle boarding and kayaking.

We were there in May, so the water was still pretty cold and we didn’t jump in, but they put on a lovely sunset cruise, which was the perfect activity to drink in more of Shelter Island and be on the water. I also got a full-body massage at The Pridwin Spa, which took my already nearly non-existent stress levels down even further. Highly recommend. The hotel also puts on wellness classes and has a fitness center.


a room with tables and chairsa room with tables and chairs

The Pridwin

The hotel’s restaurant, The Terrace, was truly d-e-l-i-c-i-o-u-s. We ate there all weekend long, for breakfast, lunch, and dinner, because, yes, we were lazy, but also because it was too good to pass up. We particularly loved the deviled eggs, the lobster roll, and the grilled chicken club for lunch. For dinner, you can’t go wrong with any choice, from seafood to steak. Don’t miss out on the raw oysters, the Heritage chicken, or the steak frites, btw.


If you’re looking for a low-key summer getaway where all types of activities are at your fingertips and you want to get a ton of excellent pics out of the deal/elevate the whole mood of your Instagram, this is the destination for you. We were totally entertained, full of exceptional food, and completely relaxed the whole time—kinda hard to accomplish with a baby in tow, I might add!

JSYK, The Pridwin is a seasonal hotel that opens for an extended summer, from May 10 to October 10. But you can book online year-round!

(FYI: The writer received comped accommodations and meals during this getaway.)

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