Where to Stay in Gloucester, MA
Steps from the working waterfront, minutes from the beaches, and surrounded by Cape Ann’s galleries, seafood, and salt air — The Highliner is where Gloucester feels like home. Here’s everything you need to plan the trip, and the best way to book it.
» Check Availability & Book Direct
Why stay at The Highliner
- In the heart of it all — walk to the harbor, restaurants, shops, and galleries.
- Boutique, coastal, and calm — uniquely designed rooms inspired by Cape Ann.
- Minutes to the beaches — Good Harbor and Wingaersheek are a short drive.
- Book direct, get more — best available rate, a welcome on arrival, and late checkout when available.
Plan your Gloucester trip
Everything to see, do, and taste on Cape Ann — from our blog:
Things to do
- The Ultimate Gloucester Bucket List: 40+ Best Things to Do in 2026
- Gloucester’s Hidden Gems: A Local’s Guide to the North Shore’s Best-Kept Secrets
- The Ultimate Guide to Art Galleries in Cape Ann
On the water & whale watching
- Gloucester Whale Watch: Complete Guide 2026
- What Makes a Cape Ann Whale Watch an Unforgettable Ocean Journey?
- Gloucester’s Working Waterfront After Dark
Beaches
Food & drink
Seasonal guides
- Cape Ann in the Fall: A Gloucester Guide
- Gloucester After Labor Day: What’s Still Open in the Fall
- Gloucester Schooner Festival 2026: The Complete Guide
- Spring in Gloucester, MA: Why It’s the Best Time to Visit
- Romantic Getaways on the Massachusetts Coast
Where to stay in Gloucester: FAQ
Where should I stay in Gloucester, MA?
The Highliner Hotel — boutique and downtown, walkable to the harbor, restaurants, and galleries, and a short drive to the beaches. Book direct for the best rate plus perks.
Is The Highliner close to the beach and harbor?
Yes — steps from the working waterfront and minutes from Good Harbor and Wingaersheek beaches.
What is there to do nearby?
Whale watching, beaches, seafood, Cape Ann galleries, the Schooner Festival, and scenic drives to Rockport and Essex (see the guides above).
Why book directly?
Our best available rate plus a welcome amenity and late checkout when available — value you won’t get through third-party sites.
