Cheap Vacations in Massachusetts

Choose two or more items and save on your trip:

Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3 out of 5
Seaport District
per person
Jan 2 - Jan 7
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

4 out of 5
East Boston
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
The Boxer

The Boxer

4 out of 5
West End
Save 100% on your flight
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Hilton Garden Inn Boston Brookline, MA

Hilton Garden Inn Boston Brookline, MA

3 out of 5
per person
Jan 2 - Jan 7
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)

3-night Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
The Dagny Boston

The Dagny Boston

4 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
The Boxer

The Boxer

4 out of 5
Save 100% on your flight
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Save 100% on your flight
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3 out of 5
Save 100% on your flight
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Homewood Suites by Hilton Boston Seaport District

Homewood Suites by Hilton Boston Seaport District

3 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea

2.5 out of 5
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)

4-night Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Newport North - Middletown, an IHG Hotel

Holiday Inn Express Newport North - Middletown, an IHG Hotel

2.5 out of 5
per person
Jan 10 - Jan 14
found 15 hours ago
Roundtrip flight included
Burbank (BUR) to Providence (PVD)
Omni Providence Hotel

Omni Providence Hotel

4 out of 5
per person
Jan 10 - Jan 14
found 15 hours ago
Roundtrip flight included
Burbank (BUR) to Providence (PVD)
The Beatrice

The Beatrice

3.5 out of 5
per person
Jan 10 - Jan 14
found 15 hours ago
Roundtrip flight included
Burbank (BUR) to Providence (PVD)
The Dean Hotel, an Ash Hotel

The Dean Hotel, an Ash Hotel

3.5 out of 5
per person
Jan 10 - Jan 14
found 15 hours ago
Roundtrip flight included
Burbank (BUR) to Providence (PVD)
Hotel Providence, Trademark Collection by Wyndham

Hotel Providence, Trademark Collection by Wyndham

4 out of 5
per person
Jan 10 - Jan 14
found 15 hours ago
Roundtrip flight included
Burbank (BUR) to Providence (PVD)
Residence Inn by Marriott Boston Watertown

Residence Inn by Marriott Boston Watertown

3 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Le Méridien Boston Cambridge

Le Méridien Boston Cambridge

4 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Blue Beach Motel

Blue Beach Motel

2.5 out of 5
per person
Jan 10 - Jan 14
found 15 hours ago
Roundtrip flight included
Burbank (BUR) to Providence (PVD)
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
per person
Jan 14 - Jan 17
found 20 hours ago
Roundtrip flight included
San Diego (SAN) to Boston (BOS)
The Boxer

The Boxer

4 out of 5
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Boston (BOS)

5-night Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3 out of 5
per person
Jan 2 - Jan 7
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
The Boxer

The Boxer

4 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Hyatt Regency Boston

Hyatt Regency Boston

4 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
The Newbury Boston

The Newbury Boston

5 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)

6-7 night Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea

2.5 out of 5
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
The Boxer

The Boxer

4 out of 5
Save 100% on your flight
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
Save 100% on your flight
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3 out of 5
Save 100% on your flight
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Save 100% on your flight
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Save 100% on your flight
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
Save 100% on your flight
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Save 100% on your flight
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Save 100% on your flight
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)
YOTEL Boston

YOTEL Boston

4 out of 5
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip flight included
Jacksonville (JAX) to Boston (BOS)

Top places to visit in Massachusetts

Quincy Market showing a city, an administrative buidling and heritage architecture
FlightsFlightsHotelsHotels

Boston

Boston

Flight deals to Massachusetts

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Dec 5 - Sun, Dec 8
LAX
Los Angeles
BOS
Boston
$175 Roundtrip, found 5 days ago
$175
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, Dec 5 from Los Angeles to Boston, returning Sun, Dec 8, priced at $175 found 5 days ago
Thu, Jan 23 - Tue, Jan 28
PDX
Portland
BOS
Boston
$224 Roundtrip, found 18 hours ago
$224
Roundtrip
found 18 hours ago
Select Bargain Flight flight, departing Thu, Jan 23 from Portland to Boston, returning Tue, Jan 28, priced at $224 found 18 hours ago
Sat, Dec 14 - Wed, Dec 25
LAX
Los Angeles
BDL
Hartford
$247 Roundtrip, found 13 hours ago
$247
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Sat, Dec 14 from Los Angeles to Hartford, returning Wed, Dec 25, priced at $247 found 13 hours ago

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.