The Best Hotels in Gloucester, MA

The 12 Best Hotels in Gloucester, Massachusetts

Over on the southern shore of Cape Ann in Massachusetts, you’ll find a small city with a rich history. Originally settled in 1623, it became the city of Gloucester in 1642. Since its founding, it’s blossomed as a hub for the fishing industry. Fishing is at the town’s heart, as evidenced by the beloved bronze Fisherman’s Memorial, which honors all those lost at sea. 

But in more recent years, Gloucester has become a more publicly known city thanks to its fishing history being at the center of the National Geographic show Wicked Tuna. Perhaps that’s partly why the small city has been welcoming more and more visitors year after year. 

From the historic landmarks to the serene beaches, Gloucester is a perfect place to spend a summer getaway. But where should you stay when you visit? The Gloucester area boasts hotels where presidents once rested their heads, bed and breakfasts hosted by knowledgeable locals, and modern boutique hotels with antique touches. 

There are so many unique places to choose from that you may have a hard time picking the perfect one. So we’ve created a list of the 12 best hotels in Gloucester, MA, to help you plan your dream vacation to this charming, scenic destination.

  • Short on time and don’t want to read the whole article? Here are our top 3 picks!
  1. Addison Choate
  2. The Cove at Rockport
  3. Sally Webster Inn

Disclaimer: This post may contain affiliate links. If you make a purchase or booking through one of our links we may earn a small commission (don’t worry, it’s at no extra cost to you).

Where to Stay in Gloucester, MA

Where to Stay in Gloucester, MA: Best Hotels

Because Gloucester can get so cold in the winter, you’re likely going to want to plan your vacation to this coastal city when the weather heats back up. In fact, many hotels and activities in the area shut down completely in the winter, so you may find that it’s difficult to plan a trip outside of the spring and summer anyway.

Gloucester is only 41.5 square miles, with much of it being water. It’s also essential to note that while Gloucester has plenty of fun and scenic things to do for visitors, it is a city that’s highly tied to the fishing industry. Many of the people you’ll come across on your trip here are a part of that tradition. 

So, when you choose a place to stay in or around Gloucester, you’ll want to stay in an area that’s more for recreation than work. You’ll find that many hotels here are near the beach, as you’ll likely want to spend your days enjoying the white sand and clear blue water.

In this city, you won’t really find many chain hotels. Instead, you’ll find charming bed and breakfasts and boutique hotels built into historic homes. Many of these hotel owners are lifelong Gloucester residents who will be able to give you insider tips on how to explore the city like a local. 

Because Gloucester isn’t particularly large, you may find that there aren’t too many hotels directly in the city. But staying in another Cape Ann town, like neighboring Rockport, will put you just as close to the beaches and provide you with just as beautiful views.

The 12 Best Hotels in Gloucester, MA

1. Atlantis Oceanfront Inn Gloucester

Cool Hotels in Gloucester, Massachusetts: Atlantis Oceanfront Inn Gloucester
Photo: Atlantis Oceanfront Inn Gloucester

Is there anything more lovely than waking up to the sun rising over the ocean? Located just one mile away from Good Harbor Beach, the Atlantis Oceanfront Inn is easily one of the best Gloucester hotels, with one of the biggest reasons being that every room has an ocean view. 

In addition to a beautiful view, each room comes with complimentary Wi-Fi, a refrigerator, air conditioning, a TV, a microwave, and a coffee station complete with Starbucks coffee. You’ll also enjoy access to the fitness center and outdoor pool. 

Start each morning off by taking a walk down to the hotel’s ocean-view terrace and then head to the on-site breakfast cafe, open seven days a week from May to October. You’ll take in the sounds and sight of the lapping waves as you dine on a breakfast filled with homemade treats and fresh, seasonal ingredients.

2. Harborview Inn

Photo: Harborview Inn

As one of the best hotels in Gloucester, MA, you’ll find the Harborview Inn lives up to its name as this place overlooks the town’s outer harbor, one of the oldest and most beautiful working harbors in America. This location puts you right in the middle of the best activities and attractions in Gloucester, with easy walks to the shops, restaurants, and beaches.

This charming bed and breakfast features a lush garden and a cozy lobby area complete with a fireplace to warm you up when the nights get colder. Wi-Fi is free throughout the property, as is self-parking. 

You’ll love that all the rooms are individually decorated to feel like your home away from home. Plus, each room has its own private bath. Other amenities include complimentary bottled water, TVs with cable and Netflix, and air-conditioning. 

Living up to the bed and breakfast name, this hotel offers a free continental breakfast each morning. Here you’ll find fresh fruits and pastries from around the Cape Ann area. Fuel up and get ready to spend a day in the sun!

3. Cape Ann Motor Inn

Boutique Hotels in Gloucester, Massachusetts: Cape Ann Motor Inn
Photo: Cape Ann Motor Inn

Want to stay just steps away from the beach? You’ll love staying at the Cape Ann Motor Inn, one of the coolest hotels in Gloucester. Located directly on Long Beach, with each access into both Gloucester and neighboring Rockport, all rooms in this hotel overlook the ocean. From your window, you’ll wake up to the sight of the gorgeous Thacher Island and its twin lighthouses.

Each room includes a portable air-conditioning unit, sliding glass doors leading to ocean-view balconies, a flat-screen TV, free Wi-Fi, and a private bath. You can also choose to stay in a room with the additional benefit of a fully-stocked kitchenette. 

Each morning, you can take in the rising sun on the beachside deck with a complimentary coffee and pastry in hand. And in the evenings, cozy up with your sweetheart in the quaint lobby, complete with a roaring fireplace. 

Staying here also comes with some additional perks, like discounts. If you want to rent a surfboard or stand-up paddleboard, you can receive 10 percent off at Cape Ann SUP if you show your room key.

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4. The Vista

Unique Gloucester Hotels: The Vista
Photo: The Vista

The Vista is a beachside hotel that offers sweeping views of Good Harbor Beach from all rooms. In fact, when you stay here, you’ll have access to a walkway that will take you directly to Good Harbor Beach in less than 10 minutes. But because beach weather isn’t all the time in Massachusetts, The Vista closes for the winter, with a reopening date of April.

This dog-friendly hotel is also very family-friendly. Children under the age of 11 stay free, while children between the ages of 11 to 18 are only $10 per night. Rooms come with a patio with ocean views, a refrigerator, a microwave, heating, air conditioning, and a private bath with a tub. 

You’ll be greeted with a complimentary continental breakfast each morning before you head to the beach. Don’t want to jump into the ocean? Jump into the seasonal heated pool instead, which also features ocean views. 

5. Addison Choate

Unique Hotels in Gloucester, Massachusetts: Addison Choate
Photo: Addison Choate

Located in neighboring Rockport, Addison Choate is one of the best boutique hotels in the Gloucester area. You’re not only nearby Gloucester’s beaches, but you’re also within walking distance of multiple Rockport beaches. 

The Addison Choate is actually the first boutique hotel in Rockport and is known for its upscale yet comfortable feeling. Though the building itself is historic, inside, you’ll find modern touches and technology. 

All rooms come with marble bathrooms, giving them a spa-like quality. Meanwhile, the bedrooms boast all-new mattresses that are hybrid coil and foam, giving you the perfect balance of firm and soft. 

Other amenities include smart TVs with multiple streaming service options, free Wi-Fi, a refrigerator, and bathrobes. You can also take advantage of the hotel’s fleet of rental bikes to get around.

In the morning, you’ll wake up to breakfast in either the dining room or the awning-shaded porch, which overlooks the perennial garden. But the hotel continues to treat you throughout the day. In the afternoon, you’ll find treats like homemade cookies. And in the evenings, you’ll curl up with a good book by the garden with a cup of complimentary tea or coffee in hand.

6. Seafarer Inn

Cool Gloucester Hotels: Seafarer Inn
Photo: Seafarer Inn

Open from May to the end of October, the Seafarer Inn is one of the best hotels in Gloucester, MA. Located in neighboring Rockport, this inn has a long history. It was originally built in 1890 as the Straitsmouth Inn. It’s changed hands many times over the years, with the current owners purchasing it in 2013. 

The new owners set about making it a more modern place to stay in the Gloucester area. A wrap-around porch was added for guests to take in the cool ocean breezes, as well as a new gas fireplace for when those breezes turn too chilly. 

Each room is uniquely decorated, with many including beautiful ocean views, kitchenettes, and electric fireplaces. All rooms also come with private bathrooms, air conditioning, heating, a refrigerator, free Wi-Fi, and a TV with cable. You’ll also start each day with a free continental breakfast, which is always a nice touch.

7. Sally Webster Inn

Best Hotels in Gloucester, Massachusetts: Sally Webster Inn
Photo: Sally Webster Inn

The Sally Webster Inn is the Addison Choate’s sister property and another one of the best places to stay near Gloucester. While the Addison Choate focuses on more modern touches, the Sally Webster is all about style, bringing bright touches and antique finishes. 

When you stay here, you’re just steps away from downtown Rockport, with all its restaurants, shops, and galleries. And you’re just a quick drive or bike ride away from the area’s local beaches. 

The Sally Webster’s guest rooms are each eclectically designed and feature different decor. Each of the five rooms is named for a famous female pirate. Book the beautiful blue-toned Madame Cheng room, named for the Cantonese commoner who would become the Pirate Queen of China. Or stay in the red-and-blue Anne Bonny room, named for the Irish-born pirate and privateer who took the Caribbean by storm.

No matter which room you book, you’ll find luxurious linens, handwoven rugs, private and recently-remodeled bathrooms, a seating area, free Wi-Fi, flat-screen TVs with streaming services, and a coffee station. Some rooms also have a working fireplace. Whichever room you choose, you’ll be greeted with a fresh-baked breakfast each morning.

8. The Beech Tree

Unique Gloucester Hotels: The Beech Tree
Photo: The Beech Tree

What started as a beautifully restored 1860s Greek Revival home has become one of the best hotels in Gloucester, MA. This bed and breakfast is located in neighboring Rockport, just a short walk away from the downtown area. You’re also just a quick stroll from the Rockport MBTA station, which provides you with access to many top Massachusetts stops, like Boston and Salem.

The hotel features three rooms: the Folly Cove Suite, Marga’s Room, and Hannah Jumper’s Room. In each one, you’ll find fine linens, spa robes, a soaking tub with a rainforest showerhead, air conditioning, a flat-screen TV, and complimentary Wi-Fi. You’ll also wake up to a home-cooked breakfast each morning, fueling you up to start your day of exploring.

9. The Cove at Rockport

Unique Hotels in Gloucester, Massachusetts: The Cove at Rockport
Photo: The Cove at Rockport

Formally called the Peg Leg Inn, the Cove at Rockport has become one of the coolest hotels in the Gloucester area. This hotel is built around convenience. 

When you arrive, you won’t have to wait in line to check in. You can do it straight from your mobile device, which also functions as your room key. And when you need a member of their concierge team to help you plan your Gloucester vacation, their mobile concierge is just a tap away.

The Cove is just steps away from Front Beach, and you can watch a beautiful sunset over the ocean from the cozy patio. But because this is a beachside property, it’s not open when the weather isn’t beach-friendly. The Cove opens back up for the year in March. 

This pet-friendly hotel’s rooms include free Wi-Fi, individual heating and cooling units, smart TVs, a refrigerator, a private bathroom with a tub, hardwood floors, oversized windows, a Keurig coffee maker, and two beach chairs.

10. Rockport Inn and Suites

Unique Gloucester Hotels: Rockport Inn and Suites
Photo: Rockport Inn and Suites

Located in Rockport, just a short drive away from Gloucester, is the Rockport Inn and Suites, one of the best boutique hotels in Gloucester. This hotel puts you right by downtown Rockport, just a quick stroll away from the art galleries, shopping, and restaurants. 

The pet-friendly rooms at this hotel boast free Wi-Fi, fine linens, an HDTV, guest-controlled heating and cooling, a coffee maker, a microwave, and a refrigerator. Some rooms also include a sitting area, a pullout sofa, and a full kitchen.

Wake up to a complimentary continental breakfast before you spend your day at the beach, or get a workout in at the fitness room before you dive into the indoor pool. This hotel has plenty of touches that make it feel like home, from the 24-hour coffee and tea service to the free daily newspaper.

11. Yankee Clipper Inn

Cool Hotels in Gloucester, Massachusetts: Yankee Clipper Inn
Photo: Yankee Clipper Inn

What makes the Yankee Clipper Inn one of the coolest Gloucester hotels is that it hardly feels like a hotel at all. It’s a 1929 art deco mansion that sits upon a rocky bluff overlooking the ocean. This Rockport hotel has an impressive list of former guests, including President John F. Kennedy, John Lennon, and Bette Davis.

As one of the most luxurious places to stay in Gloucester, you may not ever want to leave. You’ll take a dip in the seasonal outdoor saltwater pool, curl up with a book in the gazebo as you stare out over the ocean, or play a game of bocce ball on the new courts that also come with an ocean view. Plus, you’ll greet each morning with a hot breakfast that’s made to order.

Each room of the Yankee Clipper Inn comes with an HDTV, air conditioning, heating, Egyptian cotton towels, free Wi-Fi, and Keurig coffee makers. Although there isn’t a refrigerator in each room, there is a public guest fridge in each of the hotel’s three buildings. Some rooms also include an ocean, garden, or pool view.

12. Harbor Light Inn

Where to Stay in Gloucester, Massachusetts: Harbor Light Inn
Photo: Harbor Light Inn

The Harbor Light Inn is slightly further away from Gloucester as it can be found in nearby Marblehead. But it’s the perfect fit for someone who wants to spend some time in Gloucester and also explore other Massachusetts gems, like Salem. 

It’s also one of the best hotels near Gloucester if you’re looking for a romantic getaway. Preorder a bottle of wine from a premium wine list or fresh flowers, and they’ll be waiting for you upon your arrival.

There’s romance in every touch of the Harbor Light Inn. In each room, you’ll find timeless touches like chandeliers, hand carvings, antique furnishings, brasswork, and one-of-a-kind paintings. Every room is uniquely designed, so no two stays at the Harbor Light will be alike.

Some rooms offer fireplaces, jetted spa tubs, and garden or pool views. Plus, you’ll be greeted each day by a full breakfast, which you can enjoy in the dining room, in your room, or at a table in the garden. 

Afternoon refreshments are also available in the dining room daily, with offerings changing with the seasons. For a cocktail, beer, or premium glass of wine, along with small plate options, visit the on-site Tavern.

That completes our list of the 12 best Gloucester hotels! Did we miss any cool boutique hotels in Gloucester, MA? Comment below so we can add them to the list!

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  • Jacqueline Gualtieri

    Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California.

    When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes.

    Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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