Top 15 Resorts to Experience in Massachusetts

Due to its varied coastline, Massachusetts was historically termed the Bay State. The numerous bays that adorn the shoreline continue to be a significant allure and a defining characteristic of the area. However, Massachusetts, as one of the New England states, encompasses far more than its coastal features.

This state boasts a profound historical significance, with notable sites at every turn. Whether traversing the Freedom Trail—a footpath that weaves through landmarks relevant to the American Revolution—or enjoying a game at Fenway Park, where the echoes of illustrious players resonate, Massachusetts frequently reflects upon its past. Although such nostalgia could be deemed unproductive elsewhere, here it serves a purpose, as it is among the few regions globally that can genuinely be recognized as the Birthplace of a Nation.

A visit to the Bay State invariably invites an exploration of its rich history, evident in venues like the Museum of Fine Arts, the Boston Tea Party Ships, or the Bunker Hill Monument. Nevertheless, the state features numerous additional attractions worth discovering. For instance, savor a day at the picturesque Cape Cod seaside, attend a game at Fenway Park or TD Garden (the home of the Boston Celtics), cycle along the Shining Sea Bikeway in Falmouth, leisurely stroll through the Boston Public Garden, or tour Martha’s Vineyard, famously linked to the Kennedy family. The residents of Massachusetts are notably warm and hospitable to visitors, ensuring that guests can anticipate an unforgettable experience in the Bay State.

Let us examine the finest resorts in Massachusetts:

1. Hampton Terrace Inn

Encircled by a residence inspired by palatial elegance, this establishment captures the enchanting allure of the Gilded Age. Located in the heart of the Berkshires, a town rich in history, this sophisticated bed and breakfast may well serve as the ideal starting point for a Massachusetts journey. The complex comprises three buildings, each offering accommodations characterized by both sophistication and comfort. The resort is thoughtfully arranged as an expansive garden, with the pool at its center.

Hampton Terrace is also conveniently situated one mile from Wyndhurst Golf & Club, an 18-hole golf course established in 1926—another cherished New England tradition. The complex offers 14 elegantly designed rooms and suites, where guests are invited to enjoy a complimentary All-You-Can-Eat Breakfast Buffet each morning. Dining may be enjoyed in the communal lounge or at a private table for a more intimate breakfast experience.

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

2. Wequassett Resort and Golf Club

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Situated on Cape Cod, the Wequassett Resort offers access to two beautiful beaches and features 120 guest rooms and suites. While it boasts an associated championship golf course (the renowned Cape Cod National Golf Club), the property’s water elements take center stage during a stay. In addition to the beaches, where guests may rent kayaks, paddleboards, and sailboats, the resort includes two magnificent pools and a water playground themed around a pirate ship, perfect for children and the young at heart.

Moreover, the resort hosts the state’s longest-operating 4-star, 4-diamond restaurant, Twenty-Eight Atlantic, which serves exquisite New American cuisine complemented by an impressive 180-degree waterfront view. Should this not meet your preferences, the resort offers three additional dining experiences. With a mix of suites, villas, and cottages available, experiencing ocean-side hospitality at the Wequassett Resort is a highlight of any journey to the Bay State.

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

3. The Canyon Ranch – Lenox

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The Canyon Ranch in Lenox is a dedicated wellness resort that has been established following the success of a similar initiative in Tucson. Situated within the opulent Bellefontaine Mansion, it offers an array of luxurious and executive rooms and suites designed to reflect the splendor and grandeur of the estate.

Central to the resort’s offerings are the day spa and wellness center, with every aspect of a guest’s stay aimed at maximizing relaxation and rejuvenation through an extensive array of contemporary treatments and services. The on-site restaurant, which includes all meals in the resort’s package, serves remarkable healthy, gourmet cuisine, abundant in local and seasonal ingredients.

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

4. Green Harbor Resort

Source: redjacketresorts

Located in Cape Cod, the seasonal Green Harbor Resort comprises 50 self-contained suites, cottages, and villas that epitomize the distinctive charm of the region. Constructed from timber, with oceanfront views, these accommodations are fully equipped with kitchens and can comfortably sleep up to 10 guests.

While the resort is nestled on a tranquil peninsula, it remains close to the Hyannis shopping district. Visitors can partake in a variety of water sports and summer activities, including boating, paddleboarding, and parasailing. Additionally, the staff is more than willing to assist in arranging golf reservations at Black Rock Golf Course or whale-watching tours. Craft activities are also scheduled throughout the summer for children. To savor the unique essence of Cape Cod, the Green Harbor Resort should be on your itinerary next summer.

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

5. Edgewater Beach Resort

Source: expedia

Located on the shore of Nantucket Sound, the Edgewater Beach Resort features pristine beaches and the scenic dunes characteristic of Cape Cod while preserving the distinct culture of the area. Rooms are strategically placed to maximize ocean views, solidifying the resort as an exceptional destination in Cape Cod. The property includes a 7-hole putting course and 400 meters of private beach.

The hotel is within walking distance of Dennis, the cultural epicenter of Cape Cod. Guests can easily visit the Cape Cod Museum of Art, enjoy live performances at the Cape Playhouse, or explore the numerous art galleries within the town. Additionally, ocean-related activities are plentiful when the weather permits, including charter fishing, whale watching, and kayaking. For an authentic experience of Dennis on Cape Cod, the Edgewater Beach Resort is an ideal selection.

Website: http://www.edgewaterresorthoa.org

6. The Nantucket Hotel and Resort

Operating since 1891 in one form or another, the hotel on Nantucket Island has evolved into a modern and contemporary establishment offering easy access to the sights and activities the Island has to offer. With accommodations capable of sleeping up to 15 guests, the hotel serves as a perfect base for exploring the island’s rich history and character.

The Breeze Restaurant within the hotel is one of the most sought-after dining establishments on the Island, featuring a selection of seasonal local produce. Guests of the hotel also gain access to the Nantucket Club and Spa, which includes two swimming pools, a fitness center, and a full-service day spa providing contemporary treatments throughout the year. Whether as a corporate retreat, family gathering, or romantic weekend escape, the Nantucket Hotel and Resort offers a unique experience that creates lasting memories.

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

7. Winnetu Oceanside Resort

Overlooking the ocean at Martha’s Vineyard, the Winnetu Oceanside Resort is the sibling property to the Nantucket Island Hotel. Offering seasonal accommodations just 250 meters from South Beach, the Resort occupies one of the Island’s most desirable locations. Guests enjoy easy access to the shopping and entertainment districts while also reveling in the refreshing waters of South Beach.

Accommodations within the resort can host up to 8 guests. For larger groups, the Nantucket Hotel may offer more suitable arrangements, while multiple free-standing cottages enhance the resort’s offerings. The Dunes, the sole dining establishment on South Beach, provides relaxed dining alongside seasonal menus. The Resort’s concierge is delighted to facilitate access to the numerous tours and experiences available on Martha’s Vineyard. For a unique getaway, consider participating in the Resort’s Two Island Overnight Experience, which includes an overnight stay at the Nantucket Hotel.

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

8. Gabriel’s, A Provincetown Hotel

Nestled along the Cape Cod Bay, Gabriel’s features 20 rooms, some of which accommodate pets. The city of Provincetown is deeply rich in history and culture. Guests can explore locations dedicated to America’s illustrious artists or simply enjoy the idyllic atmosphere of this charming region. The property invites relaxation on sun decks or at one of the two outdoor fire pits amid tranquil gardens.

The rooms include all desired amenities, such as TV, internet access, fireplaces, and furnished balconies with picturesque garden views while enjoying a glass of local wine. During peak season, guests may enjoy a handmade breakfast in the Great Room, offering a variety of delicious options including muffins, fruity smoothies, scones, and breakfast burritos. For lunch, visitors can venture into town to experience local culinary delights at Angle’s Food (a gourmet market) or enjoy a craft beer at Provincetown Brewing Company.

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 has cultivated a reputation as a distinguished destination for the LGBTIQ community. Although oriented towards a specific demographic, the beachside location and elegantly designed facilities maintain a high standard befitting its oceanfront setting. Guests should be aware of the community typically attracted to this resort.

With a majority of rooms offering ocean views, the resort has been meticulously designed to fully leverage its picturesque location. Guests can delight in the beachfront heated pool and relax on the largest wooden deck in town, perfect for soaking up the sun and enjoying refreshing cocktails. Each afternoon at 4:00 PM, the deck transforms into an energetic dance venue with the renowned Tea Dance, featuring a variety of local and guest DJs providing lively entertainment.

Website: http://boatslipresort.com/

10. Wyndham Bentley Brook

Source: clubwyndham

The Wyndham Bentley Brook, located in Hancock, is another notable resort in the Berkshires. It serves as an all-season getaway situated at the base of the Jiminy Peak ski mountain. During winter, the resort offers a ski-in/ski-out experience, while in the warmer months, it remains an inviting destination. The vibrant foliage of Fall transforms the landscape into a picturesque scene worthy of exploration along the various hiking trails originating from the resort.

The resort features a sauna, fitness center, two swimming pools, and three tennis courts. Rooms are spacious, decorated in a modern style, and can accommodate up to 8 guests. While the winter season is the prime time to visit the Wyndham Bentley Brook, it remains a captivating place to explore during the warmer months as well.

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

11. Cape Codder Family Resort & Spa

Source: capecodderresort

Featuring an impressive indoor waterpark that remains open year-round, the Cape Codder Resort is a premier family destination. The outdoor pool, adorned with a rainbow waterfall, is also heated and available year-round. However, the true highlight is the three-story, temperature-controlled waterpark. The resort also organizes scheduled kids’ activities daily during the summer and school holidays, including live animal shows, outdoor cinema, and craft demonstrations.

The accommodations embody a family-friendly aesthetic, capable of housing up to 8 guests across various configurations. The resort offers a range of dining options, including the casual Hearth and Kettle Restaurant, as well as the more upscale Grand Cru Bar and Grill. Additionally, while the young ones enjoy the waterpark, adults can take advantage of a fitness center and day spa. The Cape Codder Resort encompasses all essentials for a memorable family holiday.

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

12. Ocean Edge Resort and Golf Club

Source: oceanedge

In Brewster, on the coast, the Ocean Edge Resort provides diverse accommodation options. Guests may choose to stay in the Mansion or the Village, but the remarkable range of activities available during their stay is sure to impress. Guests can access beachfront activities such as paddleboarding, kayaking, and swimming. Additionally, the resort features a golf course designed by the legendary Jack Nicklaus.

Within the Mansion, a variety of deluxe and executive rooms and suites are available, while the Village comprises several cottages and cabins carefully dispersed throughout the 380-acre estate. A network of bike trails interconnects the pools, fitness center, day spa, and golf course with the beach. The complex also offers a diverse selection of dining options, including the Beach Bar, where guests can enjoy meals with ocean views. The Ocean Edge Resort makes excellent use of its idyllic setting, ensuring a remarkably relaxing and enjoyable experience.

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

13. Chatham Bars Inn

Source: chathambarsinn

Positioning itself as the quintessential Cape Cod experience, the Chatham Bars Inn visually embodies everything expected from a Cape Cod resort. The establishment is aesthetically pleasing and perfectly suited for the region, with an iconic approach over grassy sand dunes. Upon entering, guests are greeted by the understated elegance of the furnishings, enhancing the overall ambiance.

The resort features a day spa and fitness center, alongside a variety of dining options. The beautifully appointed rooms capture the splendor of the location, complemented by modern, self-contained cottages distributed across the grounds. With facilities suitable for corporate events or large family weddings, Chatham Bars Inn emerges as a romantically enchanting destination tinged with nostalgia.

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

14. Nantucket Island Resorts

Source: nantucketislandresorts

Nantucket Island showcases a range of boutique hotels and inns that have collaborated to provide guests with a diverse selection of accommodation opportunities. From the red brick structure of the Jared Coffin House to the charming white timber style of the White Elephant Village and White Elephant Hotel, the Island offers something for every traveler.

Several exceptional dining options are also available on the Island. Toppers Restaurant at the Wauwinet Hotel provides an award-winning fine dining experience, while the Brant Pointe Grill at the White Elephant presents a more casual dining atmosphere. Visitors can immerse themselves in the island’s culture by visiting the whaling museum, relaxing on the beaches, or cycling around while embracing the sun and sea breeze. Nantucket Island stands out as a gem off the Bay State’s coast and offers a stunning holiday destination for families and couples alike.

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

15. The Ponds at Fox Hollow

Source: pondsatfoxhollow

The mere mention of The Ponds at Fox Hollow evokes notions of enchantment and exploration, with its secluded location in the Berkshire Mountains amplifying this sentiment. Nestled within meticulously maintained grounds and centered on an iconic mountain inn, the resort features 48 self-contained cottages, all fully equipped with kitchens, laundry facilities, and essential amenities.

The property grants guests access to a fitness center, tennis courts, and a swimming pool for warmer seasons. When snow blankets the mountain, skiing presents an option. Additionally, The Ponds at Fox Hollow boasts an impressive library whose centerpiece is a stone fireplace flanked by shelves filled with an extensive array of books. The Ponds experience is reminiscent of a time when magic and adventure felt authentic, and expression extended beyond the confines of text messages. A truly remarkable destination.

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