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The best area to stay in Cuttyhunk is the main village, located on the island's eastern side.


This is the island's only settled area, centred around the harbour and a few intersecting lanes. You'll find the general store, the fishing club, and a few small eateries here. It's the hub of island life and where most of the limited accommodation options are situated.


Couples looking for a quiet, secluded getaway will appreciate the village. It offers a chance to disconnect, with days spent walking the island's trails, fishing, or simply enjoying the ocean views. The pace is slow, and the evenings are peaceful.


Families with older children will also find the village a good base. Kids can enjoy exploring the shoreline, and the harbour provides opportunities for fishing or short boat trips.

The best time to go to Cuttyhunk is during the summer months, from late June to early September, when the weather is warmest and most services are available.


This period offers consistently pleasant temperatures, ideal for enjoying the island's outdoor activities. The ferry schedule is most frequent during these months, making travel to and from the island straightforward. You'll find the general store, tackle shop, and dining options are reliably open, providing convenience for your stay.


Couples looking for a peaceful escape will appreciate the island during this time. The warm water is superb for swimming at the beaches, and the long daylight hours allow for leisurely walks and enjoying the island's natural beauty. It's a great time for unwinding together without the crowds found in larger destinations.


For those interested in fishing, particularly striped bass, July and August are prime months. The waters around Cuttyhunk are renowned for their fishing opportunities, and charter services are readily available.

You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to ‘My Trips’ and selecting your reservation. To find flexible deals, filter your search by ‘Fully refundable property’ for hotels in Cuttyhunk.

One Key™—Expedia’s free travel rewards programme—gives you instant access to discounts with Member Prices on Cuttyhunk hotels. Plus, you’ll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Prices for hotels in Cuttyhunk often vary, but you can find a great deal from NZ$164 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by ‘Price: low to high’ for our cheapest rates.