Charming Coastal Towns of Massachusetts Vacation Packages

Offering close to 200 miles of coastline and a wide variety of landscapes, 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.

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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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

7 nights from $1,479*

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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 $1,249*

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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

  Between its beautiful beaches, historical landmarks, and quaint and tranquil towns, Massachusetts leaves little to be desired for vacationers of every kind.
• 
  Skiing in New England

  New England is a winter playground. The area boasts plenty of fantastic skiing options, whether you`re looking for heart-pumping adrenaline trails, cruising the bunny slopes, or you prefer to stay cozy and warm in the ski lodge, there are plenty of New England ski mountains that offer it all.
• 
  Historic Towns of the Northeast

  If you love natural beauty, quaint towns and opportunities to spot whales and devour fresh seafood, then the northeast is for you. From idyllic mountain villages to stunning seaside retreats, there`s just something special about historic towns of the northeast.
• 
  New England Cuisine

  New England has made a name for itself as a culinary capital for every type of foodie. There are endless reasons to plan a culinary getaway of the region, from the rich history of New England cuisine to its bountiful flavors and locally sourced ingredients. Learn the art of lobster fishing at the best spots in Maine, take a culinary tour and uncover hidden corners of New England’s cities and stop at one of the plentiful craft breweries to pair with any of these culinary delights.

Experiences and Adventures

• 
  White Mountain National Park
• 
  Green Mountains

SUGGESTED ITINERARIES

• 
  Boston - Cape Cod - Mystic - New York (Self Drive)
  8 nights from $1,808*
  ›
This Self-Drive vacation package will introduce you to these beautiful cities in Massachusetts, Connecticut and New York States. Combine with a Rental Car and start this trip with a visit to Boston and Cape Cod. After that, continue to Mystic in Connecticut (charming waterfront town nestled on the Mystic River, rich in nautical history. Finally, spend glorious days in the capital of the world; New York (world-class museums, amazing food and unforgettable views-there's always something new and exciting to discover in NYC).

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
• Hotel for 2 nights in Boston
• Rental Car for 4 days
• Hotel for 2 nights in Cape Cod
• Hotel for 2 nights in Mystic
• Hotel for 2 nights in New York City

• Driving Time
  Boston - Cape Cod: 1 hrs. 20 min. approx.
  Cape Cod - Mystic: 2 hrs. 10 mins approx.
  Mystic - New York City: 2 hrs. 25 mins approx.
  
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• 
  Boston - Portland - Camden - White Mountain Natl. Park - Woodstock - Green Mountains (Self Drive)
  13 nights from $2,609*
  ›
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.
  
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• 
  Gloucester - Kennebunkport - Concord NH - Boston (Self Drive)
  7 nights from $1,338*
  ›
These New England' States; Massachusetts, Maine New Hampshire are combined in this Self-Drive Package for an unforgettable holiday. Start in Gloucester (worth visiting for its history, seafood restaurants, whale watch cruises, artists' colony, historic houses, and its fine beaches). Then drive up to the southern Maine coastal area, to Kennebunkport (summer destination with diverse shops, restaurants and venues specially at the Dock Square area). After that, continue to Concord-NH in New Hampshire, with its well known carriage making, and the `Concord coaches`. Finally , spend a nice stay in Boston (one of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon).

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 6 days
• Hotel for 2 nights in Gloucester
• Hotel for 2 nights in Kennebunkport
• Hotel for 1 night in Concord NH
• Hotel for 2 nights in Boston

• Driving Time
  Boston Airport - Gloucester: 55 min. approx.
  Gloucester - Kennebunkport: 1 hr. 40 mins approx.
  Kennebunkport - Concord NH: 1 hr. 30 mins approx.
  Concord NH - Boston: 1 hr. 10 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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• 
  The Ultimate Fall Foliage (Self Drive)
  14 nights from $2,609*
  ›
A perfect combination of charming cities across Massachusetts, Vermont and New Hampshire with this unique opportunity to explore on your own with a rental. Combine Boston (the capital Massachusetts; home of the Boston Red Soxs and New England Patriots), The Berkshires (popular vacation destination, known for outdoor activities, colorful fall and thriving arts institutions), Manchester, Stowe (city overlooked by Mount Mansfield, known for its trails and ski slopes), White Mountains National Park (preserved forest offering various mountains, outdoor activities and full of scenic beauty for every season) and Portsmouth.

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 14 days
• Hotel for 2 nights in Boston, MA
• Hotel for 2 nights in The Berkshires, MA
• Hotel for 2 nights in Manchester, VT
• Hotel for 2 nights in Stowe, VT
• Hotel for 2 nights in White Mountains National Park, NH
• Hotel for 2 nights in Portsmouth, NH
• Hotel for 2 nights in Boston, MA

• Driving Time
  Boston - The Berkshires : 2 hrs. 30 mins. approx.
  The Berkshires - Manchester: 1 hr. 50 mins. approx.
  Manchester - Stowe: 2 hrs. 30 mins. approx.
  Stowe - White Mountains National Park: 1 hr. 55 mins. approx.
  White Mountains National Park - Portsmouth: 2 hrs. 10 mins. approx.
  Portsmouth - Boston: 1 hr. 10 mins. approx.
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• 
  Plymouth - Cape Cod - Boston (Self Drive)
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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 - 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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