Where to Stay on Cuttyhunk Island
Planning a trip to Cuttyhunk is an exciting adventure, and finding the perfect place to stay is the first step. Unlike larger tourist destinations, Cuttyhunk’s charm lies in its limited and unique accommodation options. From historic inns to private cottage rentals, your stay will be an integral part of the island experience.
Inns & Guesthouses
For a traditional island stay with historic charm, consider one of Cuttyhunk’s long-standing inns. They offer a unique experience and are often booked well in advance.
The Avalon
The Avalon is another iconic island guesthouse, offering comfortable accommodations with stunning views of Buzzards Bay. It provides a peaceful and private retreat, perfect for those looking to unwind and soak in the island’s tranquility.
The Cuttyhunk Fishing Club Inn
As one of the island’s most famous landmarks, this historic inn is a beloved destination for anglers and families alike. Overlooking the harbor, it offers a classic, rustic feel with a storied past. It’s a popular spot for those seeking a communal and timeless island getaway.
Private Cottage Rentals
For a more private and personalized stay, a cottage rental is an excellent choice. The island’s market is a mix of privately managed homes and those listed on major booking platforms.
Cottage rentals on Cuttyhunk are in very high demand and are often booked a year in advance. It is crucial to plan early, especially for summer and fall weekends.
- Online Platforms: Airbnb and Vrbo — photos, reviews, and secure booking.
- Local Resources: some rentals are managed directly by homeowners or local agents.
The Long Shack
Located on Tower Hill Road and has a full kitchen, cozy ambiance and can sleep up to six guests.
Pete’s Place
Offers 10 unique rental properties of various sizes throughout the island.
CuttyQuad
A 4-unit home located in the middle of town on Broadway with kitchen, living room space, and two bedrooms.
Military & Coast Guard Lodging
For military members and their families, there is a special recreational lodging facility managed by the U.S. Coast Guard — a former lifeboat station converted into a house with 2 separate apartments, rentable separately or as the whole house. Available via lottery to authorized users (active duty, National Guard, reservists, retired military, etc.).
