15 Best Resorts in Massachusetts

Written by Darren tcc
Updated on
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Because of its textured coastline, Massachusetts was early on nicknamed the Bay State. The number of bays lining the shore remains a main attraction and a feature of the landscape. But Massachusetts, one of the New England states, is much more than that.

The state has a rich history, with iconic locations around every corner. Whether you are exploring the Freedom Trail, a walking trail that snakes through locations of significance in the American Revolution, or sitting in the stands of Fenway Park recalling the ghosts of famous players of the past, Massachusetts has one eye in the rear-view mirror. And while that kind of retrospection would be counter-productive almost anywhere else in the world, here it kind of makes sense, as it is one of the few places in the world that can genuinely be called the Birthplace of a Nation.

While a trip to the Bay State always warrants exploration into its impressive history (the Museum of Fine Arts, the Boston Tea Party Ships, or the Bunker Hill Monument), there are certainly other features to explore. Take a day at the Cape Cod seaside. Visit Fenway Park, or TD Garden (home of the Boston Celtics). Ride along the Shining Sea Bikeway in Falmouth, stroll through Boston Public Garden, or visit Martha’s Vineyard, home of the Kennedy family. The people of Massachusetts are incredibly generous and welcoming of visitors (as long as they aren’t New Yorkers), and guests of the Bay State are certain to enjoy a memorable trip.

Let’s have a look at the best resorts in Massachusetts:

1. Hampton Terrace Inn

Centered around a palatial-inspired home, here you will encounter the thrilling glamour of the Gilded Age. Located in the heart of the Berkshires, a town steeped in history, this elegant bed and breakfast is quite probably the perfect place to begin a Massachusetts adventure. There are 3 buildings in the complex, each offering accommodation that is both elegant and comfortable. The resort is designed as a large garden, with the pool as its centerpiece.

Hampton Terrace is also only 1 mile away from Wyndhurst Golf & Club, an 18-hole golf course built in 1926 (golf is another fine New England tradition). There are 14 rooms and suites available in the complex, and the guests are invited to dine at on-site All-You-Can-Eat Breakfast Buffet, each morning. You can choose to dine in the community lounge or request a private table for a more personal breakfast experience.

Website: https://www.hamptonterrace.com/lenox-inn.html

2. Wequassett Resort and Golf Club

Wequassett Resort and Golf ClubSource: wequassett
Wequassett Resort and Golf Club

Located on Cape Cod, the Wequassett Resort has access to 2 beaches, and 120 guest rooms and suites. While there is a championship golf course associated with the resort (The Cape Cod National Golf Club no less), it is the water that acts as the central feature of a stay here. As well as the beaches, from which guests can hire kayaks, paddle boards, and sailboats, there are two magnificent pools and a water playground around a pirate ship, just for the kids and anyone else who wants to be a pirate (so … anyone).

The resort is also home to the state’s longest-operating 4-star, 4-diamond restaurant, Twenty-Eight Atlantic, which offers New American cuisine and an extraordinary, 180-degree waterfront view. If this isn’t to your taste, there are three other dining experiences available at the Resort. With a mixture of suites, villas, and cottages available for guests, the ocean-side experience of the Wequassett Resort is one not to be missed during any trip to the Bay State.

Website: http://www.wequassett.com/

3. The Canyon Ranch – Lenox

The Canyon Ranch – LenoxSource: canyonranch
The Canyon Ranch – Lenox

A dedicated wellness resort, the Canyon Ranch, Lenox, has been developed following the success of a similar venture in Tucson. The resort operates out of the palatial Bellefontaine Mansion and offers a range of deluxe and executive rooms and suites that are styled to match the luxury and majesty of the overall property.

The day spa and wellness center are the central focuses of the resort, however, and every element of your stay is geared towards facilitating the treatments and services that will maximize your relaxation and rejuvenation. With a variety of contemporary treatments and services available, everything the guest needs is attended to. The on-site restaurant (all food is included in the cost of the stay) prepares magnificent meals of healthy, gourmet cuisine, featuring local and seasonal produce in abundance.

Website: https://www.canyonranch.com/lenox/

4. Green Harbor Resort

Green Harbor ResortSource: redjacketresorts
Green Harbor Resort

Situated in Cape Cod is the seasonal Green Harbor Resort. The resort is constituted of 50 free-standing suites, cottages, and villas that reflect the unique style and character of Cape Cod. Timber oceanfront construction, with fully equipped kitchens, and sleeping up to 10, there is certain to be room for everyone.

The resort is located on a quiet peninsula, however, is still close to the Hyannis shopping district. Guests will also enjoy multiple water sports and activities that are active all summer, including boating, paddle boards, and parasailing. The operators are also very happy to arrange reservations for golf at Black Rock Golf Course, or whale-watching tours. In addition, there are craft activities planned on-site all summer for the kids. To enjoy a slice of Cape Cod character, give Green Harbor Resort some time next summer.

Website: http://www.redjacketresorts.com/green-harbor-resort/

5. Edgewater Beach Resort

Edgewater Beach ResortSource: expedia
Edgewater Beach Resort

On the edge of Nantucket Sound, the Edgewater Beach Resort provides access to the pristine beaches and clean dunes of Cape Cod, while retaining the unique character of the region. With rooms carefully placed to receive ocean views wherever possible, the resort makes for a perfect Cape Cod destination. There is a 7-hole putting course on site, and 400 m of private beach.

The hotel is located within walking distance of Dennis, the cultural center of Cape Cod. Guests can easily tour the Cape Cod Museum of Art, watch live theatre at the Cape Playhouse, or just explore the myriad of art galleries hosted in the town. Added to these experiences are the ocean activities available when the weather suits, such as charter fishing, whale watching, and kayaking. To experience the unique character of Dennis on Cape Cod, the Edgewater Beach Resort makes for a perfect destination.

Website: http://www.edgewaterresorthoa.org

6. The Nantucket Hotel and Resort

The hotel on Nantucket Island has been operating in one form or another since 1891. Now it represents a modern, and contemporary facility that offers walking distance access to all the sights and activities you would want to enjoy on the Island. With rooms that can sleep up to 15 people, the Hotel is a perfect base camp to explore the history and character of the Island.

The Breeze Restaurant in the Hotel is one of the most popular eateries on the Island, offering a range of seasonal local produce lovingly prepared. Hotel guests can also gain access to the Nantucket Club and Spa, which hosts two swimming pools, a fitness center, and a full-service day spa offering modern treatments all year. As a corporate retreat, family gathering or romantic weekend away, the Nantucket Hotel and Resort offers a distinct experience that will leave lasting memories.

Website: http://www.thenantuckethotel.com/

7. Winnetu Oceanside Resort

Overlooking the ocean at Martha’s Vineyard is the sister resort to the Nantucket Island Hotel, Winnetu Oceanside Resort. Offering seasonal accommodation only 250 meters from South Beach, the Resort sits in the Island’s most desirable location. Guests enjoy walking distance access to the shopping and entertainment centers of the Island, while also gaining access to the clear waters of South Beach.

Rooms in the resort can sleep up to 8 people (for larger groups, the Nantucket Hotel may be a better destination), and there are a series of free-standing cottages that complement the offering. The resort also hosts The Dunes, the only restaurant on South Beach, offering relaxed dining and seasonal menus. The concierge at the Resort is happy to arrange access to any of the numerous tours and experiences that are available from Martha’s Vineyard. To gain a unique perspective, it may be worth trying the Resort’s Two Island Overnight Experience, and staying a night at the Nantucket Hotel.

Website: http://www.winnetu.com/

8. Gabriel’s, A Provincetown Hotel

Located along the Cape Cod Bay peninsula, Gabriel’s offers 20 rooms, some of which are pet friendly. The city of Provincetown is a region deeply invested in its history and culture. Guests can tour locations dedicated to some of America’s greatest artists, or just soak in the atmosphere of this beautiful region. On the property, guests can relax on the sun decks, or at one of the 2 outdoor fire pits as you enjoy the gardens.

The rooms come with all the amenities you could want, including a TV, internet access, fireplaces, and furnished balconies from which guests can enjoy the views over the gardens while sipping some local wine. During the high season, guests can head to the Great Room to enjoy a handmade breakfast including items like muffins, real fruit smoothies, scones, breakfast burritos, and more! And for lunch, you can head out into the town and experience some of the local cuisine such as Angle’s Food (a gourmet market), and for a craft beer head to Provincetown Brewing Compay.

Website: https://www.provincetownhotel.com/?utm_source=google&utm_medium=GMB

9. Boatslip Beach Club and Resort

The Boatslip Beach Club and Resort in Provincetown is not a family resort. Over the years, the Beach Club has built up a reputation as a quality destination for the LGBTIQ community, and while the beachside location and beautifully crafted and decorated buildings uphold the standard of the oceanfront location, guests should be aware of the community the resort generally attracts.

With the majority of the rooms enjoying ocean views, the resort has been carefully designed to take full advantage of its location. There is a beachfront heated pool, and the largest wooden deck in town, where guests can relax in the sun and soak in the cool sea breeze while sipping cocktails. At 4:00 daily, however, the deck erupts into the greatest dance party ever hosted, the Tea Dance, with a range of local and guest DJs cranking out music until late. The Boatslip Beach Club provides an individual, high-energy holiday destination in Provinceville.

Website: http://boatslipresort.com/

10. Wyndham Bentley Brook

Wyndham Bentley BrookSource: clubwyndham
Wyndham Bentley Brook

Another Berkshires resort is the Wyndham Bentley Brook, in Hancock. The resort is an all-season destination at the base of the Jiminy Peak ski mountain. During the winter the resort is ski-in/ski-out, however in the warmer months, it is still worth a visit. The foliage changes color during Fall and lights up the mountain with the dragon’s breath. Hiking across the mountain along any of the trails and snaking out from the resort is an absolute must.

The resort is otherwise equipped with a sauna, fitness center, two swimming pools, and three tennis courts. The rooms are spacious and styled with a modern tone and the capacity to sleep up to 8 guests. While the winter season is the ideal time to visit the Wyndham Bentley Brook, you should definitely consider it during the warmer seasons to really experience the beauty of the region.

Website: https://www.clubwyndham.com/cw/resorts/wyndham-bentley-brook.page

11. Cape Codder Family Resort & Spa

Cape Codder Family Resort & SpaSource: capecodderresort
Cape Codder Family Resort & Spa

Equipped with an amazing indoor waterpark that is open all year, the Cape Codder Resort is an ideal family destination. The outdoor pool with rainbow waterfall is also heated and open for guests all year. But it pales into insignificance against the 3 story, the temperature-controlled masterpiece that is the waterpark. The operators of the resort don’t stop there either. During summer and school holidays there are scheduled kids’ activities every day like live animal shows, outdoor cinema, and craft demonstrations.

The rooms themselves share the family styling of the resort and are able to sleep up to 8 guests in a range of configurations. There are a number of dining options available at the resort, including the casual menu at the Hearth and Kettle Restaurant, or the more refined atmosphere of the Grand Cru Bar and Grill. In addition, while the kids are tearing it up in the water park, there is a fitness center and day spa available for the adults. Nothing has been left amiss in the development of the Cape Codder Resort, and it is a perfect holiday destination for families of all sizes.

Website: https://www.capecodderresort.com/

12. Ocean Edge Resort and Golf Club

Ocean Edge Resort and Golf ClubSource: oceanedge
Ocean Edge Resort and Golf Club

On the coast in Brewster, the Ocean Edge Resort offers choices of accommodation. Guests can stay in the Mansion, or in the Village, but either way, the incredible array of activities available during their stay will not fail to impress. Guests have access to the beach and water activities like paddle boards, ocean kayaks, and swimming. Inland of the resort guests gain access to the golf course which was designed by the legendary Jack Nicklaus.

The Mansion complex includes a range of deluxe and executive rooms and suites, while the Village is made up of a variety of cottages and cabins spread carefully around the 380-acre property. Bike trails spread like spider webs through the resort, connecting the pools, fitness center, day spa, and golf course with the beach. The complex also hosts a number of dining options, including the Beach Bar, where guests can enjoy their meal overlooking the ocean. The Ocean Edge Resort makes perfect use of its location, and provides a remarkably relaxing and enjoyable stay.

Website: http://www.oceanedge.com/resort/

13. Chatham Bars Inn

Chatham Bars InnSource: chathambarsinn
Chatham Bars Inn

Styling itself the quintessential Cape Cod experience, the Chatham Bars Inn is, visually, everything one would expect from a Cape Cod resort. The building itself is picturesque and perfect for the region, while the approach over the grassy sand dunes is nothing short of iconic. Once you step inside the building, however, the impact is magnified by the glorious, but simple elegance of the furnishings.

There is a day spa and fitness center on site, and a number of dining options. The rooms are beautifully dressed to capture the majesty of the location, and are complemented by modern, free-standing cottages dotted across the property. With a function center perfect for corporate functions, or large family weddings, the Chatham Bars Inn is a magnificently romantic destination, with a touch of bright, and hopeful nostalgia thrown in for good measure.

Website: http://www.chathambarsinn.com/

14. Nantucket Island Resorts

Nantucket IslandSource: nantucketislandresorts
Nantucket Island

On Nantucket Island, a number of boutique hotels and inns have pooled their resources to offer guests a wonderfully diverse range of accommodation options. From the red brick of the Jared Coffin House, to the distinctive white timber construction style of While Elephant Village and the White Elephant Hotel, the Island is sure to offer something for every traveler or group.

There are also several excellent dining options on the Island. Toppers Restaurant at the Wauwinet Hotel offers fine dining at award-winning levels, while at the White Elephant, the Brant Pointe Grill provides a more casual experience. While exploring the Island visitors can visit the whaling museum, hit the beaches or just jump on a bike and tour the surroundings while soaking in the sun and the sea breeze. Nantucket Island is a jewel off the coast of the Bay State, and a truly beautiful holiday spot for families and couples alike.

Website: https://www.nantucketislandresorts.com/

15. The Ponds at Fox Hollow

The Ponds at Fox HollowSource: pondsatfoxhollow
The Ponds at Fox Hollow

Just the name of this place conjures up images of magic and adventure, and the secluded location among the Berkshire Mountains does nothing to dispel those images. Situated on beautifully maintained grounds and centered around an iconic mountain inn, the resort itself is made up of 48 self-contained cottages, each fully equipped with a kitchen, laundry, and all the amenities you might need.

The complex provides guests with access to a fitness center, tennis courts, and a swimming pool for warmer weather. When the snow settles in skiing the mountain becomes an option. However, The Ponds at Fox Hollow also boasts a magnificent library. The centerpiece here is the stone fireplace, shepherded on both sides with shelves of books. The entire experience of the Ponds is an acknowledgment of a finer time when magic was real, the country was clean, and people used more than 140 characters to express an idea. Truly magnificent.

Website: http://www.pondsatfoxhollow.com/

15 Best Resorts in Massachusetts:

  • Hampton Terrace Inn
  • Wequassett Resort and Golf Club
  • The Canyon Ranch – Lenox
  • Green Harbor Resort
  • Edgewater Beach Resort
  • The Nantucket Hotel and Resort
  • Winnetu Oceanside Resort
  • Gabriel's, A Provincetown Hotel
  • Boatslip Beach Club and Resort
  • Wyndham Bentley Brook
  • Cape Codder Family Resort & Spa
  • Ocean Edge Resort and Golf Club
  • Chatham Bars Inn
  • Nantucket Island Resorts
  • The Ponds at Fox Hollow