Experienced Host! Steps to Beach! 7BR Island Retreat w/ Firepit, Bikes, Porches

Hi there! We’re so glad you found us.

Nearly two years ago, we discovered this hidden gem on our favorite island—and it’s been a dream come true to share it with guests like you. We live just about an hour away in New Hampshire with our three wonderful kids, our amazing new daughter-in-law and precious new grand daughter.

We’re a family who loves to travel, gather with friends, and make lifelong memories—and we designed Chestnut Hill Inn with those exact moments in mind. Whether you’re here for a reunion, retreat, or just a little escape, we’re honored to be part of your story.

Welcome to the island—we hope you love it as much as we do!

We’ve been vacationing on Long Island for over 15 years, and it quickly became our favorite place to be. When our daughter was little, we’d ask, “Would you rather go to Disney or Long Island?” She’d always say, “Long Island!” From the moment you step off the ferry, the salty ocean breeze and slower pace of life set the tone for a relaxing, unforgettable stay.

This island has everything we love—gorgeous beaches, stunning coastlines, and endless outdoor adventures—but what truly draws us in is how it feels. The absence of traffic lights, the welcoming community, and the beauty of untouched nature make it the perfect escape from everyday life. Whether it’s exploring the beaches, hunting for treasures with our kids, or fishing for striped bass, there’s always something new to discover here.

We love the simplicity of island life—there’s no need for a packed itinerary. Days are spent soaking up the sun, swimming in the ocean, or walking the conservation trails. Even in cooler months, the ocean invites you in for a cold plunge. The slower pace makes it easy to reconnect with each other, yourself, and what really matters.

The local community is tight-knit, and the island's charm is something you can’t find just anywhere. From the easy walk to two beautiful beaches, to the nearby pier and bakehouse, everything is close, accessible, and full of charm. Whether you’re here for a family reunion, a getaway with friends, or a peaceful retreat, Long Island provides the perfect backdrop for making lasting memories.

After visiting as guests for so many years, we found Chestnut Hill Inn and knew it was the perfect place to share with others. Now, we’re excited to offer it to families and friends looking for a peaceful escape. Long Island will always hold a special place in our hearts, and we’re thrilled to welcome you to our island paradise!

What Makes Chestnut Hill Inn Unique?

Nestled on serene Long Island, Maine, Chestnut Hill Inn is more than just a vacation home—it’s a place to create lasting memories with family and friends. The property offers a rare combination of comfort, seclusion, and natural beauty, making it the ideal retreat for larger groups or multi-generational families. Here’s what makes it stand out:

Spacious & Cozy: With 7 bedrooms (4 with ensuite bathrooms) and an additional futon-equipped room, the inn accommodates up to 16 guests. It’s perfect for family reunions, group retreats, or a getaway with loved ones, offering plenty of space to gather while still feeling intimate.

Fully Equipped for Groups: The commercial kitchen is equipped to handle meals for a crowd, featuring 2 fridge/freezers, ample cookware, and everything you need to serve large meals. Whether preparing a feast or a quick snack, it’s a dream for chefs of any skill level.

Multiple Gathering Areas: The inn is designed for togetherness, with two dining areas, a cozy living room with a TV, a library, and peaceful sitting areas. There’s even a poker table for some friendly competition, plus puzzles and games for all ages.

Outdoor Paradise: Two wraparound porches let guests enjoy the breathtaking views and fresh ocean air. The screened-in porch with seating and a TV is perfect for relaxing evenings. Plus, a firepit with eight chairs makes for cozy nights under the stars, roasting marshmallows with loved ones.

Perfect Location: Just a short walk to two of Maine’s most beautiful beaches, the inn is ideally positioned for beach lovers and outdoor enthusiasts alike. It’s also close to the island pier, bakehouse, and general store, offering easy access to essentials and local charm.

Island Magic: Long Island’s unhurried pace and natural beauty make it a place to unwind. The refreshing ocean breeze, quiet beaches, and peaceful atmosphere create the perfect backdrop for meaningful moments with those you cherish.