Massachusetts Uncovered: A Comprehensive Travel Handbook

Discover Lake Winnipesaukee

Lake Winnipesaukee stands out as one of the Massachusetts’ best lake. 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.

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Top 3 Fun 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.

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Must See Attractions

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Fenway Park

Stadium

Fenway Park is one of the oldest and most iconic Major League Baseball stadiums, renowned for its charming architecture, the iconic “Green Monster” left-field wall, and its status as the beloved home of the Boston Red Sox.

Isabella Stewart Gardner Museum

Speciality Museums

The museum is a cultural gem known for its stunning architecture, world-class art collection, and its founder’s unique vision, displayed within a Venetian-style palace setting.

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, making it the tallest waterfall in the state of Massachusetts.

Where to Sleep

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Lakes to Discover

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1. Lake Quannapowitt

16 Miles

This is a picturesque lake surrounded by parks and walking trails, offering scenic views and opportunities for relaxation.

2. Walden Pond

19 Miles

Walden Pond in Concord is a serene lake surrounded by wooded trails, inviting visitors to connect with nature.

3. Long Pond

36 Miles

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

42 Miles

Cape Cod Bay is a significant body of water along the Massachusetts coast, known for its beaches, towns, and sunsets.

5. Lake Quinsigamond

44 Miles

This lake is a popular recreational lake known for its boating and rowing events, offering picturesque views and a tranquil escape.

6. Lake Winnipesaukee

103 Miles

Lake Winnipesaukee is the largest lake in the state, offering a vast expanse for boating, fishing, and enjoying waterfront activities.

7. Otis Reservoir

116 Miles

One of the largest lakes in the state, this lake is a popular destination for boating, fishing, and camping, offering a getaway in the Berkshires.

8. Ashmere Lake

129 Miles

Ashmere Lake provides a serene setting for swimming, fishing, and kayaking, making it a destination for a quiet lakeside escape.

Annual Events and Festivals

Thursday, July 4, 2024

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.

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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 maritime traditions of the region. The highlight of the festival is the grand Parade of Sail, where an impressive fleet of historic schooners parades through the harbor.

Thursday, 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.

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Top Hiking Trails

Great Blue Hill via Skyline Trail

705 Hillside St, Milton, Massachusetts 02186

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 3 mile loops takes less than 2 hours to complete.

Visit their website for more information

Mount Watatic and Nutting Hill via Wapack Trail

Watatic Southern Terminus, MA-119, Ashburnham, Massachusetts 01430

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.

Visit their website for more information

Blue Hills Skyline Trail

Blue Hills – Skyline Trail, Quincy, Massachusetts 02169

The Blue Hills Skyline Trail offers a captivating journey through the Blue Hills Reservation, just south of Boston. This popular trail, which covers approximately 7 miles, showcases the diverse ecosystems and scenic beauty of the area. Beginning at the Trailside Museum, the trail leads hikers through woodlands, open meadows, and rocky terrain, providing a mix of environments that make for a dynamic and engaging hiking experience.

Visit their website for more information

Best Golf Courses

Miacomet Golf Course

12 W Miacomet Rd, Nantucket, Massachusetts 02554

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.

Visit their website for more information

Old Sandwich Golf Club

247 Old Sandwich Rd, Plymouth, Massachusetts 02360

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.

Visit their website for more information

Pinehills Golf Club

54 Clubhouse Dr, Plymouth, Massachusetts 02360

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.

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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.

Visit their website for more information

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.

Visit their website for more information

Sudbury Canoe and Kayak

Paddling

Located on the picturesque Lake Sudbury, Sudbury Canoe and Kayak offers a range of paddlecraft rentals, including canoes, kayaks, and stand-up paddleboards. LWhether gliding along the lake’s calm waters, exploring hidden coves, or simply enjoying the peaceful ambiance, Sudbury Canoe and Kayak allows individuals and families to embrace the beauty of nature from the unique perspective of a paddlecraft.

Visit their website for more information

Best Winter Activities

01

01 / Ice Fishing

Ice fishing in Massachusetts draws outdoor enthusiasts to the state’s frozen lakes and ponds. Popular destinations for ice fishing in Massachusetts include lakes such as Quabbin Reservoir, Lake Chaubunagungamaug (Webster Lake), and Wachusett Reservoir. Whether in pursuit of Perch, Trout, Bass, or other cold-water fish, ice fishers must patiently wait for the tell-tale tug on their lines beneath the icy surface.

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01

02 / Downhill Skiing

With ski resorts such as Wachusett Mountain, Jiminy Peak, and Berkshire East, Massachusetts offers a range of slopes and trails catering to both beginners and seasoned skiers. Skiers can carve through groomed trails, navigate moguls, and enjoy the thrill of downhill descents. Many resorts provide amenities such as ski schools, equipment rentals, and cozy lodges. As families, friends, and solo adventurers hit the slopes, shared passion for winter sports creates a vibrant atmosphere, making skiing an integral part of outdoor recreation in Massachusetts.

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03 / Snowshoeing

With a plethora of trails and nature reserves, including places like Mount Greylock State Reservation and the Appalachian Trail, snowshoeing enthusiasts can venture into Massachusetts snow-covered landscapes. The state provides a variety of terrains for all skill levels, allowing both beginners and experienced snowshoers to enjoy the sport. Whether navigating wooded trails or open fields, snowshoeing in Massachusetts provides an escape into the beauty of winter.

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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

There are many historical sites in Massachusetts but don’t forget to explore the beautiful scenery in the Berkshire Mountains or go hiking in the Appalachian Trail. The state offers a variety of outdoor activities such as whale watching off the coast, kayaking, and bird watching.

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Jet Skiing

Massachusetts is a beautiful and exciting destination for vacationers, and one of the best ways to experience its unique charm is by staying in a vacation rental. By choosing a vacation home instead of a hotel, you’ll enjoy more space, privacy, and flexibility during your trip. You’ve got some amazing options from charming beach houses and historic cabins to luxurious apartment rentals.

Whether planning a romantic getaway, a family vacation, or a solo adventure, renting a vacation home in Massachusetts provides the perfect setting. You can select from beautiful coastal towns like Cape Ann, popular beach destinations in Cape Cod, or picturesque rural retreats in areas like Norwich Lake. Many rentals have sought amenities like air conditioning, private beach access, and pet-friendly policies.

Key Takeaways

– Vacation rentals in Massachusetts offer more space, privacy, and flexibility compared to hotels.
– Choose from various rental options, including beach houses, cabins, and luxury apartments in popular destinations.
Booking platforms like Lake, Vrbo, Airbnb, and Vacasa make finding and reserving your ideal Massachusetts vacation rental easy.

Why Choose A Vacation Rental in Massachusetts?

Vacation rentals provide much-needed comfort when you’re away from home. No more cramped hotel rooms or noisy neighbors. Imagine having a fully equipped kitchen, multiple bedrooms, and your yard or balcony to relax on. Sounds appealing.

Not only do vacation rentals offer more space and amenities, but they can also cater to your specific requirements. Are you traveling with a large group or your beloved pet? There’s a vacation rental for that. Need a place that provides a workspace or high-speed Wi-Fi? You got it. The endless customization possibilities ensure that your vacation rental aligns with your needs and preferences.

But that’s not all! Vacation rentals can save you some money, too. You can often find a better deal than traditional accommodations by choosing a vacation home. Plus, having your kitchen means you can cook meals, saving you from constantly eating out.

Now, when it comes to choosing the right destination, Massachusetts has so much to offer. From the picturesque Cape Cod beaches to the bustling city of Boston, there’s something for everyone. And with vacation rentals spread across the state, you can easily find one that allows you to explore your desired attractions and create lasting memories.

Top Destinations for Vacation Rentals in Massachusetts

Whether you’re looking for a beach getaway or a taste of historic New England, you’ll find it here.

Cape Cod

This town is a popular choice for beach lovers and families. With quaint towns like Chatham, Wellfleet, and Falmouth, you’ll have plenty of options for beautiful vacation homes. Enjoy the stunning beaches, diverse water activities, and delicious seafood while you’re there.

Provincetown

Provincetown is located at the end of Cape Cod, boasts a vibrant arts scene, unique shops, and stunning beaches. Choose from cozy homes and modern condos.

Nantucket

Nantucket is an upscale island escape with charming cobblestone streets, historic lighthouses, and luxurious vacation rentals. This destination is perfect for a more sophisticated and exclusive experience.

Plymouth

For history buffs, Plymouth and Boston are excellent choices. In Plymouth, you’ll find a range of vacation rentals near historical sites like Plymouth Rock and Plimoth Plantation.

Boston

In Boston, experience the famous Freedom Trail, as well as a bustling city atmosphere with a plethora of rental options.

Berkshires

The Berkshires in Western Massachusetts offer a peaceful retreat in stunning natural surroundings. Choose a vacation rental in this area, and you’ll be close to hiking trails, beautiful scenery, and charming small towns.

Hyannis

Hyannis is a bustling town on Cape Cod, rich in maritime history and home to the Kennedy Compound. Vacation rentals are close to popular attractions like the Cape Cod Maritime Museum and Hyannis Harbor.

Mashpee

Explore Mashpee for a mix of relaxation and adventure. This Cape Cod town has beautiful beaches, nature preserves, hiking trails, and ideal rental options for families and groups of friends.

New England

New England charm is abundant in quaint towns like Bourne and Sandwich on Cape Cod, offering vacation rentals near delightful local sights and attractions. Enjoy picturesque landscapes and witness first-hand the beauty of historic New England.

Types of Vacation Rentals in Massachusetts

Massachusetts offers various vacation rentals, from cozy cottages to spacious vacation homes. This lovely state has something for every size of group or family.

Cottages
Cottages are a popular choice for vacationers in Massachusetts. These charming and quaint rentals often come with all the comforts of home, making them an ideal option for a relaxing getaway. You can find beautiful cottages throughout the state, particularly in lake and coastal areas.

Hotels
Hotels provide a convenient and hassle-free option for those who prefer accommodations with 24-hour service and on-site amenities. Massachusetts hotels range from budget-friendly to luxurious, catering to all travelers. Some even offer unique experiences like spa treatments and fine dining options.

Houses
Houses make for a perfect vacation rental if you want a home-away-from-home experience. Ranging from modest family homes to sprawling estates, house rentals offer privacy and comfort, ideal for families or groups of friends.

Condos
When it comes to condos, Massachusetts has plenty to offer. These properties often provide access to shared amenities such as pools and gyms while still giving you the privacy and independence of your living space. Condos can be found in cities like Boston or beachside towns like Cape Cod.

Villas
Private villas are a luxurious option for those looking to indulge themselves in a lavish vacation. These upscale rentals often come with top-notch amenities, stunning views, and plenty of space. Private villas are in some of the state’s most picturesque locations, including Martha’s Vineyard and Nantucket.

Large Vacation Homes
Lastly, large vacation homes are perfect for group getaways, accommodating multiple families or large parties. These properties typically offer spacious living areas, outdoor entertainment options, and plenty of bedrooms to suit your group’s needs.

Luxury Features of Massachusetts Vacation Rentals

These upscale vacation rentals offer a range of luxury amenities, including private pools and hot tubs, modern kitchens, plush master suites, state-of-the-art entertainment systems, and other convenient features such as fitness centers and concierge services.

Affordable Vacation Rentals in Massachusetts

In Massachusetts, you can find affordable vacation rentals on platforms like Lake, Airbnb, HomeToGo, and Rent By Owner. These platforms offer a variety of accommodation options that fit different preferences and budgets. If you’re traveling with pets, Vacasa has a selection of dog-friendly vacation rentals with amenities like hot tubs and internet.

Pet-Friendly Vacation Rentals

You’ll be glad to know that there are plenty of pet-friendly vacation rental options. 

There are many pet-friendly vacation rental options available in Massachusetts. BringFido and Rent By Owner are popular websites that offer a variety of dog-friendly vacation rentals, including beach houses, cabins, and condos. From budget options to luxury homes, you can easily find a comfortable and cozy place to stay with your furry friend. 

Now, give your furry friend an extra cuddle for us!

Unique Vacation Rentals in Historical Massachusetts

Massachusetts is rich in history and offers unique accommodations that let you experience the past differently. From a cozy treehouse with floor-to-ceiling windows in the Berkshires to a historic home in Boston, here’s a list of some fascinating vacation rentals you can book for your next getaway.

Great Barrington

In Great Barrington, you will want to take advantage of the chance to stay in an octagonal glass treehouse. Located in Otis, this romantic getaway is perfect for couples who want a private retreat while still enjoying the beauty of the Berkshires. The floor-to-ceiling windows showcase the stunning unobstructed views, making you feel like you’re one with nature.

Stockbridge

If you’re heading to Stockbridge, consider booking a modern treehouse in Truro Hills. This astonishing rental offers three bedrooms, three bathrooms, a full kitchen, and amenities like wireless internet and a washer/dryer. With a high 4.9-star rating, this treehouse will surely delight anyone searching for a one-of-a-kind rental experience. The lush Truro landscapes provide the perfect backdrop for this unique accommodation.

Boston

Now, let’s talk about Boston, a city brimming with history. You can immerse yourself in the past by booking a 19th-century brick Victorian row house in the city’s South End. This 2 bedroom home has been transformed to offer modern comfort without compromising its historical charm. Enjoy the convenience of a ballroom, pool table, TV room, and wet bar during your stay.

Booking Online to Get the Best Deals

Booking your vacation rental online is a great way to ensure you get the best deals.

Step one: Research prices and discounts.

Save money by browsing through various online vacation sites like Booking.com and KAYAK. They provide you with the latest prices and deals for Massachusetts vacation rentals. Keep an eye out for discounts, where you can save up to 36% on your rental, as seen on HomeToGo.

Step two: Look for last-minute deals.

Sometimes, you can score great savings by booking your vacation rental during a last-minute deal. This often happens when operators have a few unsold slots and are willing to lower their prices to fill those vacancies. So, be ready to pack your bags and jump on those deals because who doesn’t love spontaneous trips?

Step three: Explore various types of rentals.

Not all vacation rentals are created equal. Massachusetts offers a range of options, from cozy cabins to spacious houses. Make a reservation based on your budget, group size, and preferences. Consider Rent By Owner™ for a more personalized experience, where you can filter your results and find the perfect place for your getaway.

Activities Near Your Vacation Rental

So, you’ve booked your Massachusetts vacation rental, and now it’s time to plan some exciting activities to enjoy during your stay. 

Hiking Trails

The great outdoors in Massachusetts offers various hiking trails and mountains to explore. If you’re looking to hit the trails, head to the Berkshires. This mountainous region is home to plenty of picturesque hiking spots, such as Bash Bish Falls or Mount Greylock, the tallest peak in Massachusetts. Do you prefer the coast? No problem! Massachusetts is well-known for its stunning beaches stretching along the shoreline. Cape Cod and Martha’s Vineyard are popular destinations for beachgoers looking for a relaxing coastal experience.

White-water Rafting

For the adventure-seekers, your adrenaline will surely pump while white-water rafting down one of Massachusetts’ pristine rivers. The Deerfield River in the western part of the state is perfect for rafting trips, whether you’re a beginner or an experienced rafter. This thrilling outdoor activity will give you an adrenaline rush and create unforgettable memories with your friends or family.

Dining In and Dining Out

Massachusetts is a haven for foodies and culinary connoisseurs. You’ll be spoiled for choice when it comes to dining options, as the state is home to a diverse range of restaurants serving local and international cuisines. Indulge in fresh seafood in coastal towns like Provincetown, or journey deeper inland to experience authentic farm-to-table dining in the Berkshires or countryside.

Shopping How It’s Supposed To Be

Massachusetts is filled with trendy boutiques, antique shops, and farmer’s markets. Shoppers can browse locally crafted wares and unique finds in small, charming towns like Northampton or Newburyport. Both coastal and inland areas offer an abundance of shopping destinations, so even the most discerning shopper will find something to suit their tastes.

Planning Your Trip

This state offers much, from coastal escapes to charming countryside retreats. Planning ahead is essential to make the most of your trip. 

Research local attractions, events, and must-visit sights in the area. Massachusetts has a rich history, so you should explore historic sites, museums, and landmarks. Or, if you’re more into outdoor adventures, look into nearby hiking trails, parks, or beaches for fun in the sun.

Work in some downtime during your vacation. Everyone needs a day or two to relax and recharge, so set aside space in your schedule for rest days. Use this time to unwind at your rental, explore local shops, or enjoy leisurely meals at nearby restaurants.

Remember, when planning your trip, the key is to balance exciting activities and necessary relaxation. With a well-thought-out schedule, you’ll make memories to last a lifetime during your Massachusetts vacation.

Frequently Asked Questions about Massachusetts

Before renting a vacation home in Massachusetts, keep the following tips in mind:

  • Check local taxes: Some towns charge additional taxes and fees for vacation rentals, such as the room occupancy excise tax, which is 5.7% in Massachusetts.
  • Consider the rental agreement: Read through the contract to know what is included in the fee, any potential additional charges, and the cancellation policy.
  • Research local attractions and transportation options: Ensure the property is located near attractions you plan to visit and offers convenient access to transportation facilities if needed.

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.

Camping and log cabin rentals are a fantastic choice to immerse yourself in nature. Popular options in Massachusetts include:

  • Acadia National Park, with its stunning lakes and beautiful coastline
  • Cape Ann, a coastal region renowned for its rugged beauty
  • Myles Standish State Forest offers rustic cabins as well as camping sites

Monthly vacation rentals in Massachusetts can vary significantly depending on season, size, location and amenities provided. Generally, you can find a vacation rental to suit your budget. To compare costs, consider factors such as proximity to attractions or transportation, time of year, and if it’s a pet-friendly property.

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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