Massachusetts Vacation Packages

Between the city of Boston, Cape Cod and the Islands, the North Shore, the South Shore, Western Mass and everything in between, there really is something for everyone in Massachusetts. As one of the original 13 colonies, Massachusetts has preserved more than its share of historic landmarks from as far back as the pilgrim days. But it`s not all history – Massachusetts boasts some hip cities, varied and stunning landscapes, picture perfect little postcard-towns, along with unique outdoor adventures and a ton of culture that makes this state a top destination to be discovered.

Best Vacation Packages:

Explore Massachusetts and New York as you enjoy some of its most iconic cities. Combine Boston (the capital Massachusetts; home of the Boston Red Soxs and New England Patriots), Cape Cod and New York (the capital of the world,' very famous for its diverse entertainment venues, gastronomy and nightlife). Travel through the cities with a rental car.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support;

Included:

Flight into Boston and out of New York City

Rental Car for 5 days

Pick up last day in Boston and drop off first day in New York

Hotel for 2 nights in Boston

Hotel for 2 nights in Cape Cod

Hotel for 3 nights in New York

Driving Time
Boston – Cape Cod: 1 hr 27 min approx.
Cape Cod- New York: 4 hr 36 min approx

7 nights from $1,293*

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Take Massachusetts, New Hampshire and Maine into your own hands, travelling between this popular cities with a rental car. Visit Boston (Historic city and capital of Massachusetts famous for the Boston Tea Party), White Mountains National Park, Portland and Portsmouth (Nestled near the mouth of the Piscataqua River, known for the waterfront views and the historic sites).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support;

Included:

Flight into and out of Boston

Rental Car for 7 days

Hotel for 2 nights in Boston

Hotel for 2 nights in White Mountains National Park

Hotel for 1 night in Portland

Hotel for 1 night in Portsmouth

Hotel for 1 night in Boston

Driving Time
Boston – White Mountain National Park: 2hrs approx.
White Mountain National Park - Portland: 2 hr 30 mins approx.
Portland - Portsmouth: 54 mins approx.
Portsmouth - Boston: 1 hrs 7 mins approx.

7 nights from $1,269*

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Rolling green hills, fall foliage, mountain landscapes and colonial towns, you will discover with this Self-Drive package across New England States. In Massachusetts, visit Boston (one of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon). Then, continue to Maine State and enjoy pleasant moments in Portland (small vibrant city with narrow cobblestone streets and redbrick warehouse buildings) and Camden. An unforgettable breathtaking mountain view you will find at the White Mountain National Park in the Granite State, while; the multicolor contrast in Vermont State; with those maples trees of Woodstock and the spectacular hiking trails of The Green Mountain will be an unforgettable show for your eyes!. Entrance to national parks is not included. Plan your visit according to your schedule and be sure to check each park's operating hours.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support;

Included:

Flight into Boston and out of Albany

Hotel for 3 nights in Boston

Rental Car for 11 days

Hotel for 2 nights in Portland

Hotel for 2 nights in Camden

Hotel for 2 nights in White Mountains National Park

Hotel for 2 nights in Woodstock

Hotel for 2 nights in Green Mountains

Pick Up Car: Boston Downtown; Drop Off: Albany Airport
Driving Time
Boston - Portland: 1 hr. 50 mins. approx.
Portland - Camden: 1 hr. 45 mins. approx.
Camden - White Mountains National Park area: 3 hrs. 25 mins. approx.
White Mountains National Park - Woodstock: 2 hrs. 15 mins. approx.
Woodstock - Green Mountains area: 2 hrs. 10 mins. approx.
Green Mountains - Albany, NY Airport: 4 hrs. approx.

13 nights from $2,609*

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The Western Massachusetts with its outdoor adventures and cultural experiences and a world natural beauty is offered on this Self-Drive Package!. At the Berkshires Area visit famous Boston and Springfield (the city celebrates Dr. Seuss, the beloved children's book writer and basketball's birthplace). After that, drive to New York State and spend pleasant moments discovering; Albany and Rochester (The -Kodak Town- has a long history of industry and invention, due its many innovators especially on image and photography). Then, unforgettable breathtaking view you will find at the Niagara Falls (city known for the famous Niagara Falls, the world's fastest-moving waterfall), and finally, enjoy a nice stay in Buffalo (cultural hotspot filled with trendy bars and restaurants and is dotted with architectural gems throughout its historic neighborhoods). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.;

Included:

Flight into Boston and out of Buffalo

Hotel for 3 nights in Boston

Rental Car for 10 days

Hotel for 2 nights in Springfield

Hotel for 2 nights in Albany

Hotel for 2 nights in Rochester

Hotel for 1 night in Niagara Falls

Hotel for 2 nights in Buffalo

Driving Time
Boston - Springfield: 1 hrs. 40 mins. approx.
Springfield - Albany: 1 hr. 30 mins. approx.
Albany - Rochester: 3 hrs. 30 mins. approx.
Rochester - Niagara Falls: 1 hr. 35 mins.
Niagara Falls - Buffalo: 25 mins. approx.

12 nights from $2,758*

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Interests

• 
  City and Beach Holidays in Massachusetts

  Massachusetts has everything you need for a perfect city and beach vacation getaway. Between its beautiful beaches, historical landmarks, and quaint and tranquil towns, this state leaves little to be desired for vacationers of every kind.
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  Whale Watching in the Northeast

  Imagine being within feet of some of the most graceful, rare mammals in the world! Whale watching off the Northeast coast will allow you to experience sights you will never forget and learn all about these peaceful, endangered creatures. Meet the finback, humpback, and minke whales of the Atlantic Ocean, while also enjoying the charming New England coastal towns these excursions depart from
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  Charming Coastal Towns of Massachusetts

  Offering close to 200 miles of coastline and a wide variety of landscape, Massachusetts boasts some of the most spectacular coastal towns on its shoreline. From the sandy beaches of Cape Cod, the cobbled streets and old ports of Salem to the coastal town of New Bedford, where whaling and merchant boats once docked, discovering these quintessential towns offers charm and appeal galore.

SUGGESTED ITINERARIES

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  Boston - Northampton - The Berkshires (Self Drive)
  6 nights from $1,673*
  ›
With this vacation package you will visit exciting cities in Massachusetts and New York. Combine Boston (One of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon), Northampton and The Berkshires (A popular vacation destination, known for outdoor activities, colorful fall and thriving arts institutions); with a rental car.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
• Flight into Boston and out of Albany
• Rental Car for 6 days
• Hotel for 2 nights in Boston
• Hotel for 2 nights in Northampton
• Hotel for 2 nights in The Berkshires

• Driving Time
  Boston– Northampton: 1 hr 42 min approx.
  Northampton– The Berkshires: 1hr 3 min approx.
  The Berkshires– Albany: 1hr 2 mins approx.
  
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• 
  Massachusetts and Maine Coastal (Self-Drive)
  10 nights from $2,219*
  ›
Enjoy this Road Trip to The Bay and The Pine Tree States; with their charming coastal towns. Make sure you are hungry, as you will be find many delicious lobster dishes throughout the trip. Start in Massachusetts, visiting Boston (historic city and capital of Massachusetts famous for the Boston Tea Party); then, drive to Maine State and explore: Kennebunkport, them, Boothbay Harbor (a popular yachting and tourist destination during summer time), Bar Harbor, and finally, Bangor (best-known resident, author Stephen King, the city has much to offer to visitors with its small town charm).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
• Flight into Boston and out of Bangor
• Hotel for 3 nights in Boston
• Rental Car for 8 days
• Hotel for 2 nights in Kennebunkport
• Hotel for 1 night in Boothbay Harbor
• Hotel for 3 nights in Bar Harbor
• Hotel for 1 night in Bangor

• Driving Time
  Boston - Kennebunkport: 1 hr. 35 mins. approx.
  Kennebunkport - Boothbay Harbor: 1 hr. 45 mins. approx.
  Boothbay Harbor - Bar Harbor: 2 hrs. 50 mins. approx.
  Bar Harbor - Bangor: 1 hr. 15 mins. approx.
  
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• 
  Plymouth - Cape Cod - Boston (Self Drive)
  6 nights from $994*
  ›
A coastal journey across Massachusetts State is at your disposal in this Self-Drive Package. Combine Plymouth (the America's Hometown, was the site of the colony founded in 1620 by the Mayflower Pilgrims, where New England was first established); Cape Cod (a popular summertime destination, famous for its beautiful beaches, laid-back lifestyle, and connection to the Kennedys) and Boston (one of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon), with a Rental Car. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
Included:
• Flight into and out of Boston
• Rental Car for 6 days
• Pick Up: Boston Airport/Drop Off: Boston Downtown
• Hotel for 2 nights in Plymouth
• Hotel for 2 nights in Cape Cod
• Hotel for 2 nights in Boston

• Driving Time
  Boston Airport - Plymouth: 1 hr. 5 min. approx.
  Plymouth - Cape Cod: 40 mins approx.
  Cape Cod - Boston: 1 hr. 30 mins approx.
  
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• 
  Salem and The Berkshires (Self Drive)
  5 nights from $1,239*
  ›
Explore Massachusetts, a popular option for more experienced travelers, those looking to get off the beaten path and take their own time with a rental car. Combine Boston (One of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon), Salem and The Berkshires (A popular vacation destination, known for outdoor activities, colorful fall and thriving arts institutions).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
• Flight into Boston and out of Albany
• Rental Car for 6 days
• Hotel for 1 nights in Boston
• Hotel for 2 nights in Salem
• Hotel for 2 nights in The Berkshires

• Driving Time
  Boston - Salem: 38 min. approx.
  Salem - The Berkshires: 2 hr 32 mins approx. .
  The Berkshires - Albany Airport: 1 hr 2 mins approx.
  
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  White Mountain Natl. Park - Woodstock - Albany - Niagara Falls - Self Drive
  12 nights from $3,201*
  ›
Get close to amazing natural wonders and delight yourself with dreaming landscapes and charming cities across New England States and the fantastic Empire State. With a Rental Car, combine and visit; Boston (the capital Massachusetts; home of the Boston Red Sox's and New England Patriots) in Massachusetts; then, enjoy the fantastic views at The White Mountain National Park, in The Granite State. After that, drive and enjoy the colorful fail foliage, and charming scenery of Woodstock in Vermont; before to ends this trip exploring Albany and venture to the diverse way to see the falls at the Niagara Falls (by rainbow air helicopter, jet boat or rails). Entrance to national parks is not included. Plan your visit according to your schedule and be sure to check each park's operating hours.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
• Flight into Boston and out of Buffalo
• Hotel for 3 nights in Boston
• Rental Car for 10 days
• Pick Up: Boston Downtown/Drop Off: Buffalo-Niagara Falls Airport
• Hotel for 3 nights in White Mountains National Park
• Hotel for 2 nights in Woodstock
• Hotel for 2 nights in Albany
• Hotel for 2 nights in Niagara Falls

• Driving Time
  Boston - White Mountains National Park: 2 hrs. 15 mins. approx.
  White Mountains National Park - Woodstock: 1 hr. 10 mins. approx.
  Woodstock - Albany: 2 hrs. 35 mins. approx.
  Albany - Niagara Falls: 4 hrs. 35 mins.
  Niagara Falls - Buffalo-Niagara Falls Airport: 35 mins. approx.
  
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  Boston - Providence RI - Middlesex County - New York City (Self Drive)
  8 nights from $1,523*
  ›
Beautiful panoramic views of the sea, and thrilling's cities you will discover with this Self-Drive package across Massachusetts, Rhode Island and New York States. Start in Boston (one of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon). After that, drive to Providence RI (situated at the mouth of the Providence River and offers some of the finest urban strolling in New England). Your next destination is Middlesex County (in the south central part of the U.S. state of Connecticut). Finally, have an unforgettable stay in the capital of the world; New York City, before returning home.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
• Flight into Boston and out of New York City
• Rental Car for 6 days
• Hotel for 2 nights in Boston
• Hotel for 1 night in Providence RI
• Hotel for 2 nights in Middlesex County
• Hotel for 3 nights in New York City

• Driving Time
  Boston - Providence RI: 1 hr. approx.
  Providence RI - Middlesex County: 1 hr. 30 mins. approx.
  Middlesex County - New York City: 3 hrs. 50 mins. approx.
  
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• 
  New Englands Coastal Towns (Boston - Portsmouth - Camden - Bar Harbor - Bangor - Self Drive)
  7 nights from $1,479*
  ›
A perfect combination of charming cities across Massachusetts, New Hampshire and Maine with this unique opportunity to explore on your own with a Rental Car. Visit; Boston (one of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon), and the "City of Ships"; Portsmouth (for its maritime culture) in New Hampshire State. Continue this trip, driving to these Maine charming cities; Camden (a seaside town, featuring a beautiful harbor and locally-owned shops, galleries and restaurants), Bar Harbor (getaway to the mountains and cliffs of neighboring Acadia National Park) and Bangor (best-known resident, author Stephen King, the city has much to offer to visitors with its small town charm).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
• Flight into Boston and out of Bangor
• Hotel for 2 nights in Boston
• Rental Car for 6 days
• Hotel for 1 night in Portsmouth
• Hotel for 1 night in Camden
• Hotel for 2 nights in Bar Harbor
• Hotel for 1 night in Bangor

• Driving Time
  Boston - Portsmouth: 1 hr. 15 mins. approx.
  Portsmouth - Camden: 2 hrs. 30 mins. approx.
  Camden - Bar Harbor: 1 hr. 50 mins. approx.
  Bar Harbor - Bangor: 1 hr. 15 mins. approx
  
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• 
  Salem - Portsmouth - Boston (Self Drive)
  6 nights from $2,082*
  ›
An exciting adventure through New Hampshire and Massachusetts States, discovering their coastal towns. Visit Salem (located at the north of Boston, the city its best known for The Salem Witchcraft Trials in 1692). Then, drive to The Granite State, and discover Portsmouth (nestled near the mouth of the Piscataqua River, known for the waterfront views and the historic sites). After that, get back to Massachusetts and enjoy a pleasant stay in its capital city; Boston (home of the Boston Red Soxs and New England Patriots and famous for its Boston Tea Party). Combine these destinations with a Rental Car. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
Included:
• Flight into and out of Boston
• Rental Car for 5 days
• Pick Up/Drop Off: Boston Airport
• Hotel for 2 nights in Salem
• Hotel for 2 nights in Portsmouth
• Hotel for 2 nights in Boston

• Driving Time
  Boston Airport – Salem : 45 mins. approx.
  Salem – Portsmouth: 55 mins. approx.
  Portsmouth – Boston: 1 hr. 5 mins approx.
  
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New England States

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  Maine
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  New Hampshire
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  Rhode Island

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  Vermont
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  Connecticut