Gloucester

Landmark4.7/5

Good Harbor Beach

White sand and calm water define this Gloucester beach. A creek runs across the sand, and you can swim in it too.

Landmark4.4/5

Rocky Neck beach

This Gloucester beach is a quiet place to sit and look out over the sea. The lighthouse makes a striking backdrop.

Landmark4.5/5

Eastern Point Lighthouse

White Eastern Point Lighthouse marks Gloucester Harbor’s entrance, with a rocky path leading toward Dog Bar. Waves break over the rocks.

Culture4.7/5

Beauport, Sleeper-McCann House

Gloucester's Beauport is a mansion museum, still arranged by designer Henry Davis Sleeper. Seafaring tools, George Washington images and colored glass fill the rooms, still arranged just as Sleeper left them.

Landmark4.7/5

Stage Fort Park

Harborfront park with trails along Gloucester’s shoreline and beach access. Cannons and bunkers remain from its days as a coastal fort.

Culture4.6/5

Hammond Castle Museum

Embark on a medieval adventure at Hammond Castle Museum! Perched on the cliffs of Gloucester, MA, this 15th-century-style castle boasts stunning ocean views, secret passageways, and a vast collection of artifacts. Explore the grand halls, marvel at the intricate architecture, and feel like royalty for a day. Don't forget your crown!

Eat$$4.7/5

Duckworth's Gloucester

Gloucester restaurant with sandwiches, pastries, takeout meals, and an intimate dining room. Entrees come in half or full portions.

Eat$$$4.5/5

Lobsta Land Restaurant

Craving fresh, delicious seafood in a cozy setting? Head over to Lobsta Land Restaurant in Gloucester! Located at 84 Causeway St, this local favorite serves up mouthwatering lobster rolls, crab cakes, and more. With its welcoming atmosphere and waterfront views, it's the perfect spot to indulge in a classic New England dining experience.

Eat$$$4.3/5

Blue Collar Lobster / The Gloucester House Pub

Looking for a cozy pub in Gloucester, MA? Look no further than Gloucester House Pub! This charming spot on Rogers St offers a great selection of beers, delicious pub fare, and a warm, welcoming atmosphere. Whether you're a local or just passing through, this is the perfect place to grab a pint and unwind. Cheers!

Eat$$$4.7/5

Passports Eatery and Wine Bar

Seafood-and-wine restaurant with a warm bun and butter to start. Popovers, clam chowder and haddock are among the menu’s familiar dishes.

Eat$$$4.6/5

Sugar Magnolias

Nestled on Main Street in charming Gloucester, Sugar Magnolias is a must-visit for brunch lovers. This cozy spot serves up delicious dishes like fluffy pancakes and savory omelettes. With its welcoming atmosphere and friendly staff, it's the perfect place to start your day of exploring the seaside town.

Eat$$$$4.6/5

Tonno Gloucester

Located in the heart of Gloucester, Tonno is a seafood lover's paradise! With its charming coastal vibe, fresh catch of the day, and delicious cocktails, this spot is a must-visit for anyone exploring the historic town. Don't miss out on their famous lobster rolls and decadent seafood pasta dishes. You'll be hooked!

Eat$$4.3/5

Sebastian's Pizza

Gloucester pizza restaurant with thin-crust pies and plenty of toppings.

Eat4.2/5

Cape Ann Brewing Co

Located in the heart of Gloucester, Cape Ann Brewing Co is the perfect spot for craft beer enthusiasts. With a cozy atmosphere and a wide selection of brews, this brewery offers a taste of the local craft beer scene. Don't miss out on their fresh seafood and live music events!

Cafe$$4.5/5

Zeke's Place

Made-from-scratch breakfast cafe across from Gloucester Harbor, with signs reminding you good food takes time.

Stay$$$$4.7/5

Beauport Hotel Gloucester

Rooms feature air-conditioning, private bathrooms, sea views, balconies, and modern amenities. Additional comforts include bathrobes, free WiFi, and flat-screen TVs. The restaurant offers American and seafood cuisines with vegetarian and gluten-free options. Guests can enjoy lunch and dinner in a traditional and romantic ambience. The hotel includes a seasonal outdoor swimming pool, hot tub, fitness centre, and sun terrace. Wellness packages and outdoor activities such as cycling are available. Located in Gloucester, the property is steps from Pavilion Beach and near attractions like Jeff Weaver Studio and Harbor Tours. Logan Airport is 49 km away.

Stay$$$4.7/5

Harborview Inn

Harborview Inn in Gloucester offers air-conditioned rooms with private bathrooms, sea or garden views, and modern amenities including free WiFi, TV, and work desks. Guests can relax on the sun terrace or in the garden, enjoy the outdoor seating area, and take advantage of free WiFi throughout the property. Located a 5-minute walk from Pavilion Beach and near attractions such as Jeff Weaver Studio/Gallery (600 metres) and Yankee Whale Watch (12-minute walk). Logan Airport is 49 km away. Highly rated for its friendly host, convenient location, and suitability for city trips.

Stay$$$$4.45/5

Emerson Inn By The Sea

Emerson Inn By The Sea in Rockport is housed in a historic building, offering sea views and a tranquil street setting. The property features a swimming pool with a view, sun terrace, and lush garden. Rooms include balconies or terraces, work desks, and free WiFi. Additional amenities include a lounge, outdoor fireplace, games room, and picnic area. Guests enjoy a continental buffet breakfast with juice, fresh pastries, and fruits. The bar provides a relaxing space, and concierge service assists with activities and special dietary needs. Old Castle is a 4-minute walk away, while Back Beach lies 2.2 km from the hotel. Other nearby points of interest include Motif Number 1 and Rockport Music Shalin Liu Performance Center. Logan Airport is 57 km distant.

Stay$$$4.45/5

Yankee Clipper Inn

Overlooking the Atlantic Ocean, the Yankee Clipper Inn is a 1929 art deco mansion in the seaside town of Rockport, Massachusetts.Featuring 55” flat-screen TVs, a seasonal outdoor pool (closed for 2026), and an oceanfront gazebo, this historic inn is located 1 mile from downtown Rockport, 4 miles from central Gloucester, and near an abundance of Cape Ann swimming beaches. Complimentary breakfast is served each morning, featuring made-to-order eggs, pancakes, bacon, omelets, and fresh fruit. Guest rooms are located in one of the property’s three buildings: the Main Building, the Quarterdeck House next door, and the Bulfinch House across the street.

Stay$$$4.5/5

Sally Webster Inn

Sally Webster Inn in Rockport offers private bathrooms with free toiletries, baths, and showers. Each room includes a hairdryer and complimentary WiFi. Guests can relax on the sun terrace or in the garden. The property features an outdoor fireplace and seating areas for leisure. Located less than 1 km from Front Beach and near attractions such as Motif Number 1 and Corey Tevan Gallery. Logan Airport is 55 km away. Private check-in and check-out, daily housekeeping, and reception staff speaking English ensure a comfortable stay.

Stay$4/5

Rockport Inn & Suites

Just 4.2 km from Good Harbor Beach and Captain Bill & Sons Whale Watch, this hotel offers an indoor pool and tennis courts. It features a deluxe continental breakfast, a fitness room and a business center. Guest rooms include free Wi-Fi. A flat-screen cable TV is equipped in all classic rooms at Rockport Inn and Suites. The traditionally styled rooms are pet-friendly. The rooms include a microwave, mini-fridge and coffee maker. Inn and Suites Rockport is 10.4 km from Hammond Castle. Bearskin Neck Shopping is 1.5 km away, and Liberty Tree Mall is 33.3 km away.

Stay$$$$4.45/5

Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks in Gloucester is housed in a historic building, offering sea views and a unique atmosphere. Guests enjoy a swimming pool with a view, sun terrace, and free use of bicycles. Complimentary WiFi is available throughout the property. Rooms feature air-conditioning, balconies, private bathrooms, and modern amenities such as flat-screen TVs and work desks. Located a 12-minute walk from Good Harbor Beach and near attractions like Motif Number 1 (7 km) and Rockport Music Shalin Liu Performance Center (7 km). Logan Airport is 52 km away. Guests highly rate the scenic location, delicious breakfast, and convenient location.