Vacations in Massachusetts

Vacations in Massachusetts

2 travelers

KAYAK searches hundreds of travel sites at once for vacation package deals in Massachusetts

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Bundle and saveSave money when you bundle your flight + hotel.

Search
Best Deals
Tips
Vacation information

Cheap Massachusetts package deals

These are the best prices for May 23 - 26.
Go to map

Search by stars

2+ stars3+ stars4+ stars5 stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by board

BreakfastHalf boardSelf cateringAll inclusiveMeals not included

Search by price

$387 - $622$622 - $857$857 - $1,092$1,092 - $1,327$1,327+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Massachusetts flight and hotel deals

Show all
Courtyard by Marriott Boston-South Boston - Boston - Lounge
Courtyard by Marriott Boston-South Boston - Boston - Lounge
Courtyard by Marriott Boston-South Boston
8.3 Very good
Dorchester
Free Wi-Fi
Montreal Pierre Elliott Trudeau Intl
Meals not included
3 nights + flight
$624
citizenM Boston Back Bay - Boston - Bar
citizenM Boston Back Bay - Boston - Bar
citizenM Boston Back Bay
8.9 Very good
Back Bay
Free Wi-Fi
Montreal Pierre Elliott Trudeau Intl
Breakfast
3 nights + flight
$699
Sheraton Boston Hotel - Boston - Lounge
Sheraton Boston Hotel - Boston - Lounge
Sheraton Boston Hotel
8.3 Very good
Back Bay
Pool
Pet friendly
Spa
Montreal Pierre Elliott Trudeau Intl
Meals not included
3 nights + flight
$725
Hilton Garden Inn Boston Logan Airport - Boston - Patio
Hilton Garden Inn Boston Logan Airport - Boston - Patio
Hilton Garden Inn Boston Logan Airport
8.7 Very good
East Boston
Airport shuttle
Free Wi-Fi
Pool
Pet friendly
Montreal Pierre Elliott Trudeau Intl
Meals not included
3 nights + flight
$625
DoubleTree Suites by Hilton Boston - Boston - Bedroom
DoubleTree Suites by Hilton Boston - Boston - Bedroom
DoubleTree Suites by Hilton Boston
8.6 Very good
Allston
Free Wi-Fi
Pool
Montreal Pierre Elliott Trudeau Intl
Meals not included
3 nights + flight
$570
Hilton Boston Logan Airport - Boston - Lobby
Hilton Boston Logan Airport - Boston - Lobby
Hilton Boston Logan Airport
8.2 Very good
East Boston
Airport shuttle
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$675
Hyatt Regency Boston Harbor - Boston - Building
Hyatt Regency Boston Harbor - Boston - Building
Hyatt Regency Boston Harbor
8.6 Very good
East Boston
Airport shuttle
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$648
The Langham, Boston - Boston - Lounge
The Langham, Boston - Boston - Lounge
The Langham, Boston
9.3 Wonderful
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
$868
Omni Parker House - Boston - Lobby
Omni Parker House - Boston - Lobby
Omni Parker House
8.2 Very good
Downtown
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$707
Hotel Indigo Boston Garden By IHG - Boston - Bedroom
Hotel Indigo Boston Garden By IHG - Boston - Bedroom
Hotel Indigo Boston Garden By IHG
8.3 Very good
West End
Free Wi-Fi
Pet friendly
Montreal Pierre Elliott Trudeau Intl
Meals not included
3 nights + flight
$745
Renaissance Boston Seaport District - Boston - Lounge
Renaissance Boston Seaport District - Boston - Lounge
Renaissance Boston Seaport District
8.4 Very good
South Boston
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$714
DoubleTree by Hilton Boston Bayside - Boston - Living room
DoubleTree by Hilton Boston Bayside - Boston - Living room
DoubleTree by Hilton Boston Bayside
7.8 Good
Dorchester
Airport shuttle
Montreal Pierre Elliott Trudeau Intl
Meals not included
3 nights + flight
$512
Boston Harbor Hotel - Boston - Living room
Boston Harbor Hotel - Boston - Living room
Boston Harbor Hotel
9.3 Wonderful
Waterfront
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$1,107
Holiday Inn Express Boston By IHG - Boston - Restaurant
Holiday Inn Express Boston By IHG - Boston - Restaurant
Holiday Inn Express Boston By IHG
8.4 Very good
Dorchester
Free Wi-Fi
Montreal Pierre Elliott Trudeau Intl
Breakfast
3 nights + flight
$604
The Revolution Hotel - Boston - Bedroom
The Revolution Hotel - Boston - Bedroom
The Revolution Hotel
8.5 Very good
South End
Free Wi-Fi
Pet friendly
Tampa
Meals not included
3 nights + flight
$566
The Liberty, a Luxury Collection Hotel, Boston - Boston - Building
The Liberty, a Luxury Collection Hotel, Boston - Boston - Building
The Liberty, a Luxury Collection Hotel, Boston
8.3 Very good
West End
Free Wi-Fi
Pet friendly
Montreal Pierre Elliott Trudeau Intl
Meals not included
3 nights + flight
$848

Last minute vacation packages to Massachusetts

Show all
Four Seasons Hotel Boston - Boston - Bedroom
Four Seasons Hotel Boston - Boston - Bedroom
Four Seasons Hotel Boston
9.1 Wonderful
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$3,338

When to book a vacation in Massachusetts

Price includes flights and 3 nights accommodation for 2 travelers. Prices are not fixed and may vary with time.

Tips for finding Massachusetts package deals

  • There are loads of types of vacations in Massachusetts and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travelers: Top vacation $209; Family vacation $321; Romantic vacation $372; Luxury vacation $532; Budget vacation $392.

Where to stay in Massachusetts

Our map will help you find the perfect place to stay for your vacation in Massachusetts by showing you the exact location of each hotel.

Everything you need to know for your vacation in Massachusetts

Massachusetts vacation information

Top vacation (Flight+Hotel)$209
Family vacation (Flight+Hotel)$321
Romantic vacation (Flight+Hotel)$372
Luxury vacation (Flight+Hotel)$532
Budget vacation (Flight+Hotel)$392