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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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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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 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 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.


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.


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


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 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.


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 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 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 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.

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.

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.


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.


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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