Massachusetts is a state that has it all; it is a state that is historic, but also one with a coastal beauty, exciting cities, and cozy country escapes. In fact, when I was exploring the Bay State, I stayed in both five-star downtown hotels and small ocean-facing inns. Each destination is a character in itself, and a hotel can indeed make the difference to your journey. You can visit Boston as a city break, the beaches of Cape Cod, or take a sophisticated getaway to the Berkshires, but these are five of the best hotels in Massachusetts, in terms of comfort, location, atmosphere, and actual traveler experience.
Best Hotels in Massachusetts
1. The Liberty, a Luxury Collection Hotel — Boston
2. Chatham Bars Inn — Chatham, Cape Cod
3. The Red Lion Inn — Stockbridge, The Berkshires
4. The Wauwinet — Nantucket Island
5. The Harbor Light Inn — Provincetown
5 Best Hotels in Massachusetts
1. The Liberty, a Luxury Collection Hotel — Boston
The first time one enters The Liberty is memorable. The structure on its own is a historical masterpiece. Located in the old Charles Street Jail, this hotel is an easy blend of the historical architecture and new luxury. As you enter the mammoth lobby, you get the sense of something special in the air.
The rooms at The Liberty are large, well-decorated, and comfortable, and all the features that a high-quality hotel should include. The beds are comfortable, and the higher floor views of Boston are breathtaking. During my visit, turn-down service and everything that made the stay personal and welcoming, such as locally produced teas and snacks, made the stay feel personal and warm.
The location of this hotel cannot be beaten if you are willing to visit the best places in Boston. You can walk into the Freedom Trail, Beacon Hill, and the Charles River Esplanade – evenings out. Talking about food, CLINK on-site restaurant, which serves delicious New England-driven cuisine, is something one should at least try once.
The hotel is friendly to families, the suites are spacious, and the staff are friendly, which made our stay a comfortable one. When you are with children, you can visit the parks in the vicinity or even walk a little to the historic places in Boston, and your stay at the place will be relaxing and interesting.
Address: 215 Charles St, Boston, MA 02114
Average Price: $350–$550 per night
Child-Friendly: Yes, family-friendly with spacious rooms
2. Chatham Bars Inn — Chatham, Cape Cod
Chatham Bars Inn is an escape to a storybook. This resort is situated directly on the Atlantic Ocean in Cape Cod, hence I felt relaxed as soon as I got there. This is the sense of sandy beaches and graceful dunes, and the smell of saltwater in the air.
The options of accommodation include traditional rooms and ocean suites as well as individual cottages. I was staying in a comfortable room by the ocean shore, and when I got up in the morning, one of the best things about my trip was that I heard the sea waves. The interior style is beautiful but easy-going, with warm wood and sea elements that leave you both classy and at home.
The resort boasts a magnificent pool, exclusive beach access, and numerous activities for all ages, including kayaking, bike rentals, and family beach games. Food is very good, and the on-site Twenty Eight Atlantic restaurant offers some of the best seafood I have ever had in the area (the lobster bisque was amazing).
Chatham Bars Inn is a family-friendly establishment in the real sense; the kids are offered special menus and activities, and the staff makes an extra effort to make sure that you come and enjoy your stay stress-free.
Address: 297 Shore Rd, Chatham, MA 02633
Average Price: $450–$800+ per night (seasonal)
Child-Friendly: Yes, great for families
3. The Red Lion Inn — Stockbridge, The Berkshires
One of these places, where one immediately feels like home once they enter the door, is the Red Lion Inn. The historic inn is situated in the centre of the Berkshires, and it has served up visitors who have been visiting it for almost 200 years. The atmosphere is warm, old-fashioned, and pleasant, starting with the old furniture to the hearths.
I also enjoyed walking around the town of Stockbridge, around the house where I stayed: quaint shops, art galleries, and historical sites are all within walking distance. Then, after spending the day sightseeing, it was satisfying to go back to the Red Lion, as you do to an old friend.
The guest rooms are beautiful and beautifully adorned, none of the rooms seems exactly like the other, producing the charm of the place. It has an on-site restaurant serving substantial New England food, and the breakfast in the morning was delicious and rejuvenating.
This will make this inn friendly and entertaining to families. Situated between carnal paths, artistic museums such as MASS MoCA, and seasonal festivals within the Berkshires, it can be a fantastic choice for both adults and children.
Address: 30 Main St, Stockbridge, MA 01262
Average Price: $250–$400 per night
Child-Friendly: Yes
4. The Wauwinet — Nantucket Island
Nantucket is the sort of place where one can only feel like in another world, peaceful, clean, and impossibly beautiful. The Wauwinet, in the less lively side of the island, is as charming in capturing that magic. I was here on a summer holiday, and the silence was what impressed me at first. It is the place where you can want to be quiet, elegant, and right by nature.
The rooms are luxurious in coastal style and have a very faint touch of elegance. The water is something that many people do not bother to notice, and my view of the sunset on the grounds of the hotel was one of the most memorable moments of the vacation. The service in this case is friendly and intimate, the one that knows what you like and makes you feel very welcome.
No congested beach here, but smooth dunes, calm beach, and ample room to walk or rest. The restaurant of the hotel offers perfect locally oriented food, and a dinner with sparkling waters in the evening is an unforgettable experience.
The Wauwinet is a family-friendly but more adult, tranquilized place. It is also very nice for children who like outdoor and quiet places.
Address: 111 Wauwinet Rd, Nantucket, MA 02554
Average Price: $500–$900 per night
Child-Friendly: Yes
5. The Harbor Light Inn — Provincetown
One of the liveliest beach towns in Massachusetts, Provincetown (also known as P-Town), is where The Harbor Light Inn is located, right in the center of it. This hotel is of a boutique nature. All the facilities were within walking distance, such as everything, including shops, restaurants, beaches, and art galleries.
The rooms are well furnished and super clean, giving personal touches that help you feel relaxed. The employees are sociable and are always willing to assist in making suggestions, the most local seafood places, and where to find a beach where the surf is calm enough to take a walk at sunset.
Province town is an area of nightlife and arts scene, but the Harbor Light Inn has no problem accepting families. Children spent free time in the nearby beach, Herring cove beach, and there are many ice cream stores and other casual restaurants that children are fond of.
Talking about food, you cannot skip The Lobster Pot as a fresh seafood restaurant with a view, or Canteen as a casual beach restaurant. This hotel is like a second home, whether you are walking along the pier, going through the local artisan shops, or just sitting on the sand.
Address: 29 Winthrop St, Provincetown, MA 02657
Average Price: $200–$350 per night
Child-Friendly: Yes
Conclusion
Choosing the right hotel can make all the difference in a Massachusetts getaway. Whether you want historic luxury, seaside escape, or boutique charm, this state has something for every traveler.
From Boston’s city energy to Cape Cod’s ocean breeze, the Berkshires’ quiet beauty, and Nantucket’s serene shores, each of these hotels offers a unique experience, and all made my travels in Massachusetts more memorable. Most are family-friendly and well-located for exploring top attractions, local eats, and unforgettable scenic views.
So whether you’re planning a historic city break, beach vacation, or arts-and-culture retreat, these five hotels offer comfort, character, and a touch of local flair that helps turn a good trip into a great one. Massachusetts truly has a place for every kind of traveler, and these hotels are a perfect place to start.
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