TOP 30 Charming establishment in Gloucester, Massachusetts

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The Beauport Hotel Gloucester is a luxurious lodging establishment located at 55 Commercial Street in the picturesque coastal town of Gloucester, Massachusetts, in the United States. This stunning hotel offers guests a blend of modern amenities and classic New England charm, with beautifully appointed rooms and suites that provide breathtaking views of the harbor and surrounding area. Guests can enjoy exceptional dining options, a rooftop pool, a fitness center, and easy access to the town's shops, restaurants, and attractions. Whether visiting for business or pleasure, the Beauport Hotel Gloucester offers a truly unforgettable experience for all who stay.

The Atlantis Oceanfront Inn Hotel & Breakfast Café in Gloucester, MA is a charming establishment located at 125 Atlantic Road in Gloucester, Massachusetts, United States. This institution offers a unique combination of cafe, food, lodging, and restaurant services. Guests can enjoy the best breakfast in Gloucester at the breakfast cafe, which overlooks the ocean and is open to both guests and the public seven days a week from 7:30am to 11:00am, May through October. The extensive breakfast menu features locally sourced fresh fruits and vegetables, as well as freshly baked muffins bursting with fruit every morning. In addition to the delightful dining experience, the Atlantis Oceanfront Inn Hotel & Breakfast Café is known for its pristine rooms, friendly and helpful staff, and breathtaking views of the Atlantic Ocean. Guests rave about the cleanliness of the property, the delicious breakfast offerings, and the overall peaceful and relaxing atmosphere. The hotel's convenient location allows guests to explore nearby attractions such as Rockport and Good Harbor Beach, making it the perfect place for a romantic getaway or a family vacation.

Gloucester House Rental - Belle View is a charming lodging establishment located at 57 Grapevine Road in Gloucester, Massachusetts, United States. As a real estate and travel agency, we specialize in providing luxurious house rentals with breathtaking views of the surrounding area. Our properties are meticulously maintained and offer all the amenities needed for a comfortable and relaxing stay. Whether you are looking for a weekend getaway or a longer vacation, Gloucester House Rental - Belle View is the perfect choice for your next trip to Gloucester.

The Hotel at Cape Ann Marina is a picturesque waterfront retreat located at 75 Essex Avenue in Gloucester, Massachusetts. This charming establishment offers luxurious accommodations, delicious dining options, and stunning views of the marina. Whether you're looking for a relaxing getaway or a romantic escape, this hotel has everything you need for a memorable stay. Enjoy fresh seafood at the on-site restaurant, take a leisurely stroll along the harbor, or simply relax in your well-appointed room with all the amenities you could ask for. Experience the beauty of Cape Ann at this exceptional hotel.

Cape Ann Motor Inn is a charming lodging establishment located at 33 Rockport Road in Gloucester, Massachusetts, United States. Situated right on the beautiful coastline of Cape Ann, this inn offers stunning ocean views and easy access to the beach. The comfortable rooms are equipped with modern amenities to ensure a relaxing stay for guests. The inn also features a swimming pool, picnic area, and complimentary breakfast for guests to enjoy. Whether you are visiting for a weekend getaway or a longer vacation, Cape Ann Motor Inn is the perfect choice for a peaceful and enjoyable stay on the Massachusetts coast.

The Inn at Babson Court is a charming and elegant lodging establishment located at 55 Western Avenue in Gloucester, Massachusetts. Nestled in a historic building, this boutique inn offers a unique and cozy atmosphere for guests looking to relax and unwind. The Inn features beautifully decorated rooms, modern amenities, and personalized service to ensure a comfortable stay. With its convenient location near the heart of Gloucester, guests can easily explore the town's attractions, shops, and restaurants. Whether you are visiting for business or pleasure, The Inn at Babson Court is the perfect choice for a memorable stay in Gloucester.

Cape Ann Coffees is a charming cafe, restaurant, and store located at 86 Bass Avenue in Gloucester, Massachusetts. Known for its delicious coffee and baked goods, this cozy establishment offers a welcoming atmosphere for both locals and visitors alike. In addition to their signature coffee drinks, Cape Ann Coffees also serves a variety of breakfast and lunch options, making it the perfect spot to grab a bite to eat. With its convenient location and friendly staff, Cape Ann Coffees is a must-visit destination for anyone looking for a tasty meal or a quick caffeine fix in Gloucester.

The William Haskell House is a charming lodging establishment located at 11 Lincoln Street in the picturesque town of Gloucester, Massachusetts, United States. This historic house offers comfortable accommodations and a warm, inviting atmosphere for guests to enjoy. With its convenient location near the waterfront and local attractions, the William Haskell House is the perfect place to stay for a relaxing getaway in New England. Experience traditional New England hospitality at this lovely bed and breakfast.

The Colonial Inn is a charming lodging establishment located at 28 Eastern Point Road in Gloucester, Massachusetts. This historic inn offers a cozy and comfortable stay for guests looking to immerse themselves in the rich history and scenic beauty of New England. With its picturesque location near the coast, guests can enjoy stunning views of the ocean while experiencing the warm hospitality and classic charm of a traditional colonial inn. Whether you are visiting for a weekend getaway or a longer stay, the Colonial Inn provides a peaceful retreat in a quaint and historic setting.

The Hydrangea Inn is a charming lodging establishment located at 4 Kent Circle in Gloucester, Massachusetts, United States. Guests can enjoy a complimentary continental breakfast with a variety of delicious options such as pastries, croissants, quiche, and fresh seasonal fruits. The private sitting rooms offer assorted cold drinks and snacks for guests to enjoy. Each room is equipped with cable television and complimentary high-speed internet access. The inn overlooks Historic Gloucester Harbor on beautiful Cape Ann, and is conveniently located near three beaches and Stage Fort Park with various recreational activities available.

Williams' Guest House is a charming lodging establishment located in the picturesque town of Gloucester, Massachusetts. Situated at 136 Bass Avenue, this guest house offers cozy and comfortable accommodations for visitors looking to experience the beauty of the New England coast. The welcoming atmosphere and personalized service make Williams' Guest House the perfect home away from home for travelers exploring the historic streets and stunning beaches of Gloucester. Whether you are seeking a relaxing getaway or a convenient base for exploring the area, Williams' Guest House is the ideal choice for your stay in Massachusetts.

Crow's Nest is a cozy and welcoming institution located at 334 Main Street in the picturesque town of Gloucester, Massachusetts. Serving as both a bar and lodging establishment, Crow's Nest offers a unique and charming experience for visitors. The bar provides a laid-back atmosphere where guests can enjoy craft cocktails, local beers, and delicious pub fare. The lodging accommodations are comfortable and stylish, perfect for a relaxing stay in this historic coastal town. Whether you're looking for a night out with friends or a weekend getaway, Crow's Nest is the perfect destination.

Short & Main is a charming bar and restaurant located on Main Street in Gloucester, Massachusetts. With a cozy and inviting atmosphere, this establishment is the perfect spot to enjoy delicious food and drinks with friends and family. Open Thursday through Monday from 5pm to 9pm, and on Fridays and Saturdays until 10pm, Short & Main offers a menu filled with delectable dishes and refreshing beverages. Whether you're looking for a casual dinner or a lively night out, Short & Main has something for everyone. Visit us today and experience the warm hospitality and exceptional cuisine that sets us apart from the rest.

Fishbones is a charming seafood restaurant located at 34 Central Square in Chelmsford, Massachusetts. Established in 2006, Fishbones is dedicated to serving fresh, simple, and un-complicated dishes that highlight the best of New England seafood. The restaurant's Nantucket style architecture creates a cozy and welcoming atmosphere, making guests feel right at home from the moment they walk in. Fishbones hand selects their seafood from the piers of Boston and Gloucester, ensuring that only the freshest ingredients are used in their dishes. Their shellfish, including steamer clams and oysters, undergo a rigorous 48-hour depuration process to purify them from any residual sand and bacteria.

Minglewood Harborside is a charming waterfront restaurant located at 25 Rogers Street in Gloucester, Massachusetts. With stunning views of the harbor, this establishment offers a unique dining experience that combines delicious food with a picturesque setting. From fresh seafood dishes to savory steaks, Minglewood Harborside prides itself on serving high-quality cuisine in a relaxed and inviting atmosphere. Whether you're looking for a romantic dinner for two or a casual meal with friends, this restaurant is the perfect place to enjoy a memorable dining experience in Gloucester.

Oliver's Harbor Restaurant & Bar is a charming and cozy establishment located at 64 Main Street in Gloucester, Massachusetts. Known for its delicious food and refreshing drinks, this restaurant and bar offers a welcoming atmosphere for guests to relax and enjoy a meal or drinks with friends and family. With a menu featuring a variety of tasty dishes and a fully stocked bar, Oliver's Harbor is the perfect spot for a casual dining experience or a fun night out. Come visit us and experience the warm hospitality and great food that Oliver's Harbor has to offer.

Fede Fortune is a charming lodging institution located at 370 Main Street in the picturesque town of Gloucester, Massachusetts, United States. This cozy establishment offers comfortable accommodations and a warm, welcoming atmosphere for guests to relax and enjoy their stay. With convenient access to local attractions, shops, and restaurants, Fede Fortune is the perfect choice for travelers looking to experience the beauty and charm of Gloucester. Book your stay today and experience the hospitality and comfort that Fede Fortune has to offer.

Zeke's Place is a cozy cafe and restaurant located at 66 East Main Street in Gloucester, Massachusetts. Known for its delicious food and welcoming atmosphere, Zeke's Place is a popular spot for locals and visitors alike. Whether you're looking for a hearty breakfast, a tasty lunch, or a relaxing dinner, Zeke's Place has something for everyone. Come enjoy a meal in this charming establishment and experience the warm hospitality that makes Zeke's Place a favorite dining destination in Gloucester.

1606 Restaurant & Oyster Bar is a charming and cozy establishment located in the heart of Gloucester, Massachusetts. Situated at 55 Commercial Street, this restaurant offers a unique dining experience with a focus on fresh seafood and oysters. The menu features a variety of delicious dishes prepared with locally sourced ingredients, as well as a selection of craft cocktails and fine wines. The atmosphere is warm and inviting, making it the perfect spot for a romantic date night or a casual dinner with friends. With its waterfront location and stellar reputation, 1606 Restaurant & Oyster Bar is a must-visit destination for food and drink enthusiasts in the area.

Machaca is a charming restaurant located at 14 Rogers Street in Gloucester, Massachusetts. Known for its delicious and authentic Mexican cuisine, Machaca offers a variety of flavorful dishes that will satisfy any craving. From traditional tacos and enchiladas to mouthwatering burritos and sizzling fajitas, there is something for everyone to enjoy at this cozy establishment. With a welcoming atmosphere and friendly staff, Machaca is the perfect spot to gather with friends and family for a memorable dining experience. Come taste the flavors of Mexico at Machaca today!

Passports Eatery and Wine Bar is a charming restaurant located at 110 Main Street in Gloucester, Massachusetts. This cozy establishment offers a diverse menu of delicious food options, paired with an impressive selection of wines. Whether you're looking for a casual meal with friends or a romantic dinner for two, Passports Eatery and Wine Bar is the perfect spot to enjoy a memorable dining experience. With its inviting atmosphere and attentive staff, this restaurant is sure to become a favorite among locals and visitors alike.

Virgilio's Bakery is a cozy and charming establishment located at 29 Main Street in Gloucester, Massachusetts. This beloved bakery offers a wide selection of freshly baked goods, including artisan breads, pastries, cakes, and cookies. Customers can also find a variety of specialty grocery items and gourmet products to complement their baked goods. With a warm and inviting atmosphere, Virgilio's Bakery is a popular destination for locals and visitors alike looking for delicious treats and quality ingredients.

Good Harbor Liquors is a charming liquor store located in the heart of Gloucester, Massachusetts. Situated at 340 Main Street, this establishment offers a wide selection of wines, spirits, and beers to suit every taste and occasion. Whether you're looking for a fine bottle of wine to pair with dinner or a craft beer to enjoy with friends, Good Harbor Liquors has you covered. With a knowledgeable staff ready to assist you in finding the perfect libation, this store is a must-visit destination for all your beverage needs.

The Cave is a charming food and store institution located at 44 Main Street in Gloucester, Massachusetts. This unique establishment offers a curated selection of gourmet food items, artisanal products, and specialty goods. Whether you're looking for a delicious snack, a thoughtful gift, or a special treat for yourself, The Cave has something for everyone. Come explore our cozy shop and discover a world of culinary delights waiting to be enjoyed.

Savour Wine & Cheese is a charming institution located at 76 Prospect Street in Gloucester, Massachusetts. This unique establishment offers a wide selection of fine wines and artisanal cheeses, making it a perfect destination for food and wine enthusiasts. Whether you're looking to stock up on gourmet goodies for a special occasion or simply want to treat yourself to a delicious snack, Savour Wine & Cheese has everything you need. With a cozy atmosphere and knowledgeable staff, this store is a must-visit for anyone in the area looking to elevate their culinary experience.

Cape Ann Olive Oil Co is a charming and inviting food and health store located at 57 Main Street in Gloucester, Massachusetts. This unique establishment offers a wide variety of high-quality olive oils and balsamic vinegars, sourced from around the world. Customers can sample different flavors and find the perfect pairing for their favorite dishes. In addition to their gourmet oils and vinegars, Cape Ann Olive Oil Co also offers a selection of other specialty food items and health products. Whether you're a foodie looking to enhance your culinary creations or simply looking for a healthy and delicious treat, Cape Ann Olive Oil Co has something for everyone. Visit this delightful store and experience the wonderful world of artisanal oils and vinegars.

Main Street Arts & Antiques is a charming institution located in the heart of Gloucester, Massachusetts. Situated at 124 Main Street, this unique establishment offers a delightful blend of a book store, home goods store, and antique shop all in one. Visitors can browse through a curated selection of rare books, vintage home decor, and one-of-a-kind antiques, making it the perfect destination for collectors and enthusiasts alike. Whether you're searching for a special piece to add to your home or simply looking for a unique gift, Main Street Arts & Antiques has something for everyone. Step inside and discover the hidden treasures waiting to be uncovered at this must-visit destination on Main Street.

Castaways Vintage Cafe is a unique establishment located in the heart of Gloucester, Massachusetts. This one-of-a-kind spot combines the cozy atmosphere of a cafe with the eclectic charm of a vintage clothing store. Guests can enjoy delicious food and drinks while browsing through a curated selection of retro clothing and accessories. Whether you're looking for a tasty meal, a new outfit, or just a fun place to hang out, Castaways Vintage Cafe has something for everyone. Visit us at 65 Main Street for a truly unforgettable experience.

Holy Cow Ice Cream Cafe is a charming and inviting food store located at 80 Pleasant Street in Gloucester, Massachusetts. As soon as you step inside, you are greeted with the sweet aroma of freshly made ice cream and waffle cones. This family-friendly establishment offers a wide variety of delicious ice cream flavors, sundaes, milkshakes, and other frozen treats. Whether you're craving a classic scoop of vanilla or a unique flavor like salted caramel pretzel, Holy Cow Ice Cream Cafe has something for everyone. With its cozy atmosphere and friendly staff, this cafe is the perfect place to satisfy your sweet tooth on a hot summer day.

Jim's Bagel & Bake Shoppe is a charming bakery and cafe located at 34 Railroad Avenue in Gloucester, Massachusetts. Known for its delicious bagels and baked goods, this cozy establishment offers a wide range of freshly made treats to satisfy any craving. Whether you're looking for a quick breakfast on the go or a leisurely lunch with friends, Jim's Bagel & Bake Shoppe has something for everyone. Stop by and experience the inviting atmosphere and mouthwatering flavors that have made this spot a local favorite.