Hammond Haven, Luxury Log and Timber Cottage on Jack Lake
Apsley, Ontario
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- 5
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Escape to Massachusetts: Unwind in Picturesque Lake Houses and Historic Retreats
Massachusetts, a state where colonial history meets stunning natural beauty, offers a captivating array of vacation rentals that invite you to experience its rich heritage and picturesque landscapes. Whether you’re dreaming of a tranquil lakeside retreat in the Berkshires or a cozy cottage near the historic towns of Cape Cod, Massachusetts provides the perfect setting for an unforgettable escape.
In the heart of the Berkshires, you’ll find charming lake houses in towns like Lenox and Stockbridge, where peaceful waters reflect the vibrant hues of fall foliage. These idyllic retreats offer access to cultural treasures like Tanglewood, the summer home of the Boston Symphony Orchestra, and the Norman Rockwell Museum, where you can immerse yourself in the region’s artistic legacy. For outdoor enthusiasts, the nearby Appalachian Trail offers miles of scenic hiking, while summer brings a host of festivals and farmers’ markets that celebrate local flavors and crafts.
Further east, the historic town of Concord offers a perfect blend of serene lake views and rich literary history. Stay in a charming New England home near Walden Pond, where you can follow in the footsteps of Henry David Thoreau, or explore the Revolutionary War sites that define this storied region. Concord’s vibrant events calendar includes guided historical tours and seasonal festivals that bring the town’s past to life.
Massachusetts’ vacation rentals provide a gateway to the best of New England. From the rolling hills of the Berkshires to the tranquil waters of Walden Pond, every corner of Massachusetts invites you to create memories that will last a lifetime.
Top 3 Facts about Massachusetts
01
Cranberry Central
Massachusetts is one of the leading producers of cranberries in the United States. The acidic bogs in the southeastern part of the state provide ideal conditions for cranberry cultivation.
02
Plymouth Rock
Massachusetts is home to Plymouth Rock, the legendary landing site of the Mayflower Pilgrims in 1620. It has become a symbol of the early European settlement in the United States.
03
The Birthplace of Basketball
Dr. James Naismith, a physical education instructor, invented basketball in December 1891 in Springfield, Massachusetts. The first game was played at the International YMCA Training School in Springfield.
Must See Attractions
Fenway Park
Stadium
Fenway Park is one of the oldest and most iconic Major League Baseball stadiums. It is renowned for its charming architecture, the iconic “Green Monster” left-field wall, and its status as the beloved home of the Boston Red Sox.
Martha’s Vineyard
Martha’s Vineyard is an idyllic island located south of Cape Cod, known for its picturesque landscapes, charming towns, and beautiful beaches. Accessible by ferry or small plane, the island offers a tranquil escape with activities ranging from sailing and fishing to exploring art galleries and boutique shops.
Bash Bish Falls
Nature & Parks
Found in the scenic Taconic Mountains on the Massachusetts-New York border, the falls is a natural wonder renowned for its cascading waters and lush surroundings. It is also the tallest waterfall in the state of Massachusetts.
Where to Sleep
Pet-friendly
- 5
- 2
The Round House
Big River
- 3
- 3
Pet-friendly
Villa Santorini
Gary
- 7
- 4
Pet-friendly
Camp Baxter
Gary
- 2
- 1
Pet-friendly
Sandhill Flat
Gary
- 3
- 1
Pet-friendly
- 6
- 4
Lakes to Discover
1. Lake Quannapowitt
This picturesque lake is surrounded by parks and walking trails, offering scenic views and opportunities for relaxation.
2. Walden Pond
Walden Pond in Concord is a serene lake surrounded by wooded trails, inviting visitors to connect with nature.
3. Long Pond
Long Pond is one of the largest freshwater lakes in the state, known for its clear waters, sandy beaches, and recreational opportunities.
4. Cape Cod Bay
Cape Cod Bay is a significant body of water along the Massachusetts coast, known for its beaches, towns, and sunsets.
5. Lake Quinsigamond
This lake is a popular recreational lake known for its boating and rowing events, offering picturesque views and a tranquil escape.
6. Lake Winnipesaukee
Lake Winnipesaukee is the largest lake in the state, offering a vast expanse for boating, fishing, and enjoying waterfront activities.
7. Otis Reservoir
One of the largest lakes in the state, Otis Reservoir is a popular destination for boating, fishing, and camping, offering a getaway in the Berkshires.
8. Ashmere Lake
Ashmere Lake provides a serene setting for swimming, fishing, and kayaking, making it a destination for a quiet lakeside escape.
Annual Events and Festivals
July 4, 2025
Boston Pops Fireworks Spectacular
The Boston Pops Fireworks Spectacular is a dazzling Independence Day celebration that annually transforms the banks of the Charles River into a symphony of music and lights. This iconic event features a free concert by the renowned Boston Pops Orchestra, drawing hundreds of thousands of spectators to the Esplanade. Against the backdrop of the Boston skyline, the orchestra performs patriotic tunes, contemporary hits, and classical masterpieces. The climax of the evening is a spectacular fireworks display that paints the night sky with a brilliant array of colors and shapes, reflecting over the Charles River.
September 2024
Gloucester Schooner Festival
The Gloucester Schooner Festival is an annual maritime celebration that pays homage to the city’s rich seafaring heritage. Held in September, the festival transforms the harbor into a captivating display of majestic schooners, inviting residents and visitors alike to immerse themselves in the region’s maritime traditions. The festival’s highlight is the grand Parade of Sail, where an impressive fleet of historic schooners parades through the harbor.
December 31, 2024
First Night Boston
First Night Boston is a family-friendly New Year’s Eve celebration that has been enchanting residents and visitors for decades. Families gather to enjoy interactive art installations, ice sculptures, and a procession of colorful parade floats. Streets are transformed into stages where musicians, dancers, and performers showcase their talents, creating a lively and celebratory atmosphere. The event is known for its spectacular fireworks display over the Boston Harbor.
Top Hiking Trails
Great Blue Hill via Skyline Trail
705 Hillside St, Milton, Massachusetts
Ascending Great Blue Hill via the Skyline Trail offers outdoor enthusiasts a rewarding adventure within the Blue Hills Reservation, just outside Boston. As hikers ascend, they are treated to panoramic views of the Boston skyline, the harbor, and surrounding landscapes. Reaching the summit at an elevation of 635 feet rewards hikers with a breathtaking vista. On clear days, the skyline of Boston stands in sharp relief against the horizon. This three-mile loop takes less than two hours to complete.
Mount Watatic and Nutting Hill via Wapack Trail
Watatic Southern Terminus, MA-119, Ashburnham, Massachusetts
Starting at the southern trailhead, hikers gradually ascend through a mixed forest, and as they approach the summit of Mount Watatic, they are rewarded with sweeping views of the surrounding valleys and hills. Continuing along the ridge, the 2.9-mile trail leads to Nutting Hill, where hikers can revel in the serene landscapes and, on clear days, catch glimpses of Mount Monadnock to the south. The trail offers a mix of challenging sections and more leisurely stretches, making it suitable for various skill levels; in total, the hike takes about 90 minutes to complete.
Bash Bish Falls State Park
Falls Rd, Mt Washington, Massachusetts
Home to the highest single-drop waterfall in Massachusetts, Bash Bish Falls is a must-visit for nature lovers. The hike to the falls is relatively short but can be steep in sections. The trail offers scenic views of the Taconic Mountains and the cascading waters of Bash Bish Falls, which plunge nearly 80 feet into a sparkling pool below.
Best Golf Courses
Miacomet Golf Course
12 W Miacomet Rd, Nantucket, Massachusetts
Miacomet Golf Course, nestled on the picturesque island of Nantucket, is a captivating destination for golf enthusiasts seeking a unique coastal experience. This 18-hole public course, located on the island’s south shore, combines the natural beauty of Nantucket’s landscapes with a challenging golfing layout. Miacomet’s fairways wind through rolling terrain surrounded by native vegetation, providing players with stunning views of the Atlantic Ocean and Nantucket’s pristine beaches. The course, designed by Howard Maurer, offers a mix of par-3s, par-4s, and par-5s, ensuring a diverse and enjoyable round for golfers of all skill levels.
Old Sandwich Golf Club
247 Old Sandwich Rd, Plymouth, Massachusetts
Designed by Dr Michael Hurdzan and Dana Fry, this private 18-hole championship course seamlessly integrates with the serene surroundings of Cape Cod. The layout incorporates the region’s Indigenous flora, creating a harmonious blend of aesthetics and playability. The course’s routing takes advantage of the existing topography, offering golfers stunning views of cranberry bogs, rolling hills, and mature woodlands.
Pinehills Golf Club
54 Clubhouse Dr, Plymouth, Massachusetts
Pinehills Golf Club, situated in Plymouth, Massachusetts, is a premier golf destination that offers two distinct championship courses, the Nicklaus Course and the Jones Course. Designed by legendary golfers Jack Nicklaus and Rees Jones, respectively, these 18-hole layouts provide golfers with diverse and challenging experiences. The Nicklaus Course, crafted by the Golden Bear himself, showcases his signature design philosophy, incorporating strategic bunkering, undulating fairways, and greens that demand precision and strategic shot-making.
Water Sports
Sail Cape Cod
sailing
Embark on unforgettable nautical adventures and experience the state’s scenic coastlines. The Sail Cape Cod tour company operates out of Hyannis on Cape Cod and provides an array of sailing excursions, including private charters, sunset sails, and interactive sailing lessons. Sail through the captivating waters of Nantucket Sound and Cape Cod Bay, taking in stunning views of sandy shores, historic lighthouses, and possibly even marine wildlife.
Jet Ski of New England
Jet Skiing
Jet skiing enthusiasts can experience the thrill of speeding across the waters of Massachusetts on one of its picturesque lakes. Operating on Lake Winnipesaukee, which extends into Massachusetts from New Hampshire, Jet Ski of New England offers exhilarating jet ski rentals. Lake Winnipesaukee, surrounded by rolling hills and charming towns, offers an ideal setting for jet skiing. Riders can navigate through the crystal clear waters, enjoying the freedom of open spaces and the adrenaline rush of riding the waves.
Fishing
Fishing
Fishing is a beloved pastime in Massachusetts, with fresh and saltwater options. Cape Cod and the Islands are renowned for their saltwater fishing, offering opportunities to catch striped bass, bluefish, and tuna. Inland, the Quabbin Reservoir and the Connecticut River are popular spots for freshwater fishing, where anglers can reel in trout, bass, and pike. Charter boats, fishing guides, and public piers make it easy for both seasoned anglers and beginners to enjoy this sport.
Resorts to Explore
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Family-friendly
190 Meadow St, South Lee, Massachusetts 01260
Pelham House Resort
Spa, Couples
45 Hull Shore Dr, Hull, Massachusetts 02045
Winnetu Oceanside Resort
Luxury, Family-friendly
31 Dunes Rd, Edgartown, Massachusetts 02539
Tips on Massachusetts Vacation Rentals
Public Transportation
Boston has an extensive public transportation system, including buses and the “T” subway system. Consider using public transportation to navigate the city efficiently.
Local Cuisine
Try local dishes like clam chowder, lobster rolls, and Boston cream pie. Massachusetts is also known for its seafood, so take advantage of the fresh catches.
Explore Nature
Massachusetts has many historic sites, but don’t forget to explore the beautiful scenery in the Berkshire Mountains or go hiking on the Appalachian Trail. The state offers a variety of outdoor activities, such as whale watching off the coast, kayaking, and bird watching.
Frequently Asked Questions about Massachusetts
Booking your vacation rental through an online booking site can save you time and money by allowing you to compare prices, amenities, and locations in one place. Some sites also offer discounts when you book in advance or during off-peak seasons. Be sure to check for any promotions before booking your stay.
Many lakefront houses are available for rent across Massachusetts. You can search on popular online booking sites like Rent By Owner™, which offer a range of options in various locations. Prices start from $220 per night in Orleans, a charming town on Cape Cod, for example.
Lake Winnipesaukee stands out as one of Massachusetts’ best lakes. Known as the largest lake in the state, Lake Winnipesaukee spans over 44,000 acres and boasts more than 250 islands, each contributing to the lake’s scenic appeal. The crystal-clear waters provide a perfect setting for various water activities, including boating, fishing, and swimming. The shores are lined with charming towns and vacation homes, offering a tranquil and picturesque escape.
Lake Winnipesaukee’s diverse landscapes, coupled with its recreational offerings and the surrounding New England charm, make it a popular destination for both locals and visitors seeking a quintessential lake experience in Massachusetts.
Camping and log cabin rentals are a fantastic choice to immerse yourself in nature. Popular options in Massachusetts include:
- Cape Ann, a coastal region renowned for its rugged beauty
- Myles Standish State Forest offers rustic cabins as well as camping sites
There are many picturesque lakes in Massachusetts where you can find cabin rentals for your vacation. Some popular locations to consider include:
- Norwich Lake offers a quiet and serene retreat, with rates starting from $210 per night
- The Berkshires, rich in natural beauty and known for cultural attractions
- Quabbin Reservoir for nature lovers and those seeking a peaceful escape
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