Vacations in Massachusetts

Vacations in Massachusetts

2 travellers

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

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

C$ 474 - C$ 768C$ 768 - C$ 1,061C$ 1,061 - C$ 1,355C$ 1,355 - C$ 1,648C$ 1,648+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Massachusetts flight and hotel deals

Show all
Four Seasons Hotel Boston - Boston - Bedroom
Four Seasons Hotel Boston - Boston - Bedroom
Four Seasons Hotel Boston
9 Wonderful
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,567
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
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 716
citizenM Boston Back Bay - Boston - Bar
citizenM Boston Back Bay - Boston - Bar
citizenM Boston Back Bay
8.8 Very good
Back Bay
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
C$ 816
citizenM Boston North Station - Boston - Lounge
citizenM Boston North Station - Boston - Lounge
citizenM Boston North Station
8.7 Very good
West End
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 693
The Westin Copley Place, Boston - Boston - Building
The Westin Copley Place, Boston - Boston - Building
The Westin Copley Place, Boston
8.4 Very good
Back Bay
Pet friendly
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 831
Hilton Garden Inn Boston Logan Airport - Boston - Patio
Hilton Garden Inn Boston Logan Airport - Boston - Patio
Hilton Garden Inn Boston Logan Airport
8.6 Very good
East Boston
Airport shuttle
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 714
DoubleTree Suites by Hilton Boston - Boston - Lobby
DoubleTree Suites by Hilton Boston - Boston - Lobby
DoubleTree Suites by Hilton Boston
8.6 Very good
Allston
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 745
Hilton Boston Logan Airport - Boston - Bedroom
Hilton Boston Logan Airport - Boston - Bedroom
Hilton Boston Logan Airport
8.3 Very good
East Boston
Airport shuttle
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 679
W Boston - Boston - Bedroom
W Boston - Boston - Bedroom
W Boston
8.2 Very good
Downtown
Pet friendly
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,035
Omni Parker House - Boston - Lobby
Omni Parker House - Boston - Lobby
Omni Parker House
8.3 Very good
Downtown
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 665
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
C$ 624
Wyndham Boston Beacon Hill - Boston - Lounge
Wyndham Boston Beacon Hill - Boston - Lounge
Wyndham Boston Beacon Hill
7.2 Good
West End
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 697
Eurostars The Boxer - Boston - Bedroom
Eurostars The Boxer - Boston - Bedroom
Eurostars The Boxer
7.9 Good
West End
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 651
The Atlas Hotel - Boston - Lounge
The Atlas Hotel - Boston - Lounge
The Atlas Hotel
8.9 Very good
Allston
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 869
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
8.2 Very good
West End
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 927
Boston Marriott Long Wharf - Boston - Lounge
Boston Marriott Long Wharf - Boston - Lounge
Boston Marriott Long Wharf
8.5 Very good
Waterfront
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,247

Last minute vacation packages to Massachusetts

Show all
Homestay in Boston Fields Corner Area - Boston
Homestay in Boston Fields Corner Area - Boston
Homestay in Boston Fields Corner Area
8.2 Very good
Dorchester
Free Wi-Fi
Cleveland Hopkins Intl
Breakfast
3 nights + flight
C$ 1,111
Homestay Near Near Savin Hill Area - Boston - Balcony
Homestay Near Near Savin Hill Area - Boston - Balcony
Homestay Near Near Savin Hill Area
7.7 Good
Dorchester
Cleveland Hopkins Intl
Breakfast
3 nights + flight
C$ 1,114

When to book a vacation in Massachusetts

Price includes flights and 3 nights accommodation for 2 travellers. 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 travellers: Top vacation C$ 281; Family vacation C$ 580; Romantic vacation C$ 499; Luxury vacation C$ 431; Budget vacation C$ 373.

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)C$ 281
Family vacation (Flight+Hotel)C$ 580
Romantic vacation (Flight+Hotel)C$ 499
Luxury vacation (Flight+Hotel)C$ 431
Budget vacation (Flight+Hotel)C$ 373