Massachusetts Vacation Ideas

The Cove is Cape Cod’s landmark waterfront motel. It has been greeting vacationers for more than four decades for fun in the sun, strolls on the sandy beach, water adventures, nature walks, and exploring the many great shops, boutiques and restaurants on the cape.

The 47-room motel is a hit with families looking for a fun getaway, couples needing some quality time or solo travelers who need a little serenity. The Cove has everything you need for a complete Cape Cod getaway. It’s centrally located in the center of Orleans and has immediate water access with plenty of fresh ocean air. At the Cove, you can spend your days antiquing, biking, boating, golfing, sailing or whaling. There are excellent dining options within a short walk of the motel. 

If you’re looking for a prime stretch of sandy beach, you’ve found your next vacation spot right here. At the 164-room Red Jacket Beach Resort on Nantucket Sound, you’ll enjoy the full resort experience on top of 1,000 feet of private, pristine shoreline. When you’re not splashing in the cape waters, dip your toes in the heated indoor and outdoor pools, hit the spa, or kick back at the on-site restaurant and lounge. The resort also has a seasonal Kids Club and fascinating family activities.

Red Jacket Beach has traditional Cape Cod favorites as well as themed banquets and full daily breakfast and lunch. (Dinner served in season.) The Asa Eldredge Pub serves casual cocktails and is a great place to catch the big game.

With a quarter-mile of untouched shoreline, the Chatham Bars Inn in Chatham is another great spot with private beach access and a complete resort feel. This Cape Cod hotel’s Main Inn offers one-of-a-kind guest rooms and private suites. Newer cottages with deluxe bathrooms are sprinkled throughout the property and include balconies or terraces with ocean views.

Newer spa suites are also an attraction for guests who need a little extra pampering. Spa suites have soothing in-room spa treatments and are located next to the spa and the outdoor relaxation pool. Brides-to-be love a pre-marital getaway with the ladies to a “Top Resort in New England” as recognized by Condé Nast Traveler.

The inn’s four restaurants dish up Cape Cod classics that are farm-to-table and pier-to-plate and come complete with panoramic views of the ocean.

Situated downtown within walking distance to the beach, shopping, restaurants and the harbor, The Nantucket Hotel is the island’s premier all-season destination hotel and resort. Guests who stay at the Nantucket Hotel should prepare for the quintessential New England island getaway. The inn has modern, tasteful furnishings that get the thumbs up from travelers. The Nantucket Hotel is consistently rated one of Nantucket’s bests and has won numerous Travelers’ Choice Awards over the years. Upscale hotel rooms range from one to four bedrooms, and there are also one- and two-bedroom cottages with kitchenettes and a separate living/dining area.

The hotel has a heated swimming pool, hot tub and kiddie pool, a fitness center and spa, free bike rentals. Enjoy breakfast, Sunday Brunch, lunch, and dinner at Breeze Bar and Café at the hotel.

The picturesque North Shore of Boston is an ideal getaway that’s just 40 miles from the city. With a perfect beachfront setting, luxury amenities and unsurpassed hospitality, the Beauport Hotel is a top pick for travelers who want to experience Cape Ann in a whole new light.

The upscale hotel presents city and ocean views from guest rooms equipped with contemporary furnishings, plush bedding and high-end bathrooms. For a completely relaxing experience, guests can schedule a private wellness session at the TranquiliSea Wellness Space at the hotel. The spa offers vinyasa and restorative yoga, massage therapy treatments and other pampering services for an additional charge.

The ground-floor restaurant has an oceanfront deck with panoramic water views and a relaxing fire pit. The Birdseye Rooftop Pool & Bar has a heated pool and jetted hot tub spa and a full bar serving cocktails and food.

At the expansive, 429-acre Ocean Edge Resort & Golf Club, Old-World grandeur meets the practicality and functionality of the New World. The newly renovated luxury hotel offers one-, two- and three-bedroom villas just steps from the beach and next to the cape’s only Jack Nicklaus-designed golf course. The massive resort has its own private, warm-water beach, a beach bar, a spa, five pools, three restaurants, pond access, trail access, a cardio/weight room and fitness studio, and world-class tennis.

Guests can choose from the Mansion or the Villages at Ocean Edge. The Mansion has newly refreshed two- and three-bedroom Presidential Villas with two restaurants just steps from the guest rooms. The Villages spans 380 acres and offers one-, two- and three-bedroom villas near the golf course and nine tennis courses.

Picture-perfect Plum Island Beach is a relaxing getaway in quaint Newburyport. At Blue, guests enjoy large guest rooms, suites and private cottages that are laid back, comfy and convenient. The crisp white and blue nautical design set the tone for a beach-inspired getaway with a nod to the region’s rich maritime past. The Lark Suite and the Blue Suite are two of the resort’s most popular rentals.

Guests can kick back in a lounge chair, watch the waves crash on the shore or relax with a good soak in the hotel hot tub. When it’s time to explore, you won’t have to go far to experience all the cool sights in the area like the Parker River National Wildlife Refuge, Joppa Flats, or Newburyport Brewing Company. The 13-room hotel is also pet friendly.

Sitting high on a hilltop overlooking beautiful west-central Massachusetts, the Wyndhurst Manor & Club in Lenox is a stunning Gilded Age mansion that offers a fantastic vacation getaway for all four seasons. The elegant hotel has exquisite guest rooms, wonderful contemporary amenities, on-property fine dining and exceptional attention to detail from its discerning staff. The inn is less than two and a half hours from both Boston and New York City.

The hotel makes for an ideal home base for exploring the unique region that includes highlights like the Norman Rockwell Museum and the Tanglewood Music Center, both only a short drive from the inn. At the hotel, guests can unwind at the Miraval Life and Balance Spa, hit the nearby ski slopes in winter, or schedule a tee time at the 18-hole championship golf course during warmer weather. For eats, guests can choose from two on-site restaurants or make the short journey into town for a more robust selection.

Vacationers love the idyllic Race Brook Lodge at the foot of Mount Race in Sheffield. The fully restored lodge, barn and cottages feature wide plank flooring, exposed wood beams, rustic touches and appropriate amenities to deliver the perfect amount of New England country charm. From the rich, homemade breakfast served every morning to savory dinners at the Stagecoach Tavern, the hotel will leave you full and ready to delve into the incredible Berkshires for fun year-round.

Race Brook Lodge has direct access to the Appalachian Trail, and it is only a short hike to the top of picturesque Race Brook Falls. Summers are spent hiking, biking, fishing and sightseeing in the Berkshires, while wintertime presents immaculate skiing and snowboarding opportunities at several nearby ski resorts.