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Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Save 100% on your flight
per person
Jun 25 - Jun 28
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
per person
Jun 19 - Jun 22
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Kendall Hotel

The Kendall Hotel

3 out of 5
MIT
Save 100% on your flight
per person
Jun 19 - Jun 22
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Bostonian Boston

The Bostonian Boston

4 out of 5
Government Center
Save 100% on your flight
per person
Jun 25 - Jun 28
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Jun 12 - Jun 14
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
XV Beacon

XV Beacon

5 out of 5
Beacon Hill
Save 100% on your flight
per person
Jun 12 - Jun 14
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
per person
Jun 12 - Jun 14
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
per person
Jun 12 - Jun 14
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
The Verb Hotel

The Verb Hotel

3.5 out of 5
Fenway–Kenmore
Save 100% on your flight
per person
Jun 19 - Jun 22
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
Jun 12 - Jun 14
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)

3-night Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 28
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 28
Roundtrip flight included
Chicago (ORD) 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
Jun 14 - Jun 17
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 22
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Charles Hotel

The Charles Hotel

4 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 22
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Kendall Hotel

The Kendall Hotel

3 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 22
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Bostonian Boston

The Bostonian Boston

4 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 28
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

4 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 28
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
XV Beacon

XV Beacon

5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 22
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Verb Hotel

The Verb Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 22
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 22
Roundtrip flight included
Chicago (ORD) to Boston (BOS)

4-night Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
YOTEL Boston

YOTEL Boston

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
The Boston Hotel

The Boston Hotel

2 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) 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
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
XV Beacon

XV Beacon

5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) 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
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Copley House

Copley House

3 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)

5-night Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Faraway Martha's Vineyard

Faraway Martha's Vineyard

3 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
The Attleboro House

The Attleboro House

2.5 out of 5
per person
Jun 24 - Jun 29
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
The Edgartown Inn, The Edgartown Collection

The Edgartown Inn, The Edgartown Collection

3.5 out of 5
per person
Jun 24 - Jun 29
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
The Sydney, The Edgartown Collection

The Sydney, The Edgartown Collection

3.5 out of 5
per person
Jun 24 - Jun 29
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
The Richard, The Edgartown Collection

The Richard, The Edgartown Collection

3.5 out of 5
per person
Jun 24 - Jun 29
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
The Christopher, The Edgartown Collection

The Christopher, The Edgartown Collection

3 out of 5
per person
Jun 24 - Jun 29
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
The Coco, The Edgartown Collection

The Coco, The Edgartown Collection

3 out of 5
per person
Jun 24 - Jun 29
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
Summercamp

Summercamp

3.5 out of 5
per person
Jun 24 - Jun 29
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
Vineyard Harbor Motel

Vineyard Harbor Motel

2.5 out of 5
per person
Jun 24 - Jun 29
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
per person
Jun 24 - Jun 29
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)

6-7 night Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Falmouth Tides

Falmouth Tides

2.5 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Boston (BOS)
Thomas Sea Suites

Thomas Sea Suites

3.5 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Boston (BOS)
Harbor View Hotel

Harbor View Hotel

5 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Vineyard Haven (MVY)
The Masthead Resort

The Masthead Resort

2.5 out of 5
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Provincetown (PVC)
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Boston (BOS)
Blue Water Resort

Blue Water Resort

3 out of 5
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Boston (BOS)
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Hyannis (HYA)
Chatham Tides

Chatham Tides

2.5 out of 5
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Boston (BOS)
Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Provincetown (PVC)
Pilgrim Sands on Long Beach

Pilgrim Sands on Long Beach

2 out of 5
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Boston (BOS)
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Boston (BOS)
An English Garden Bed & Breakfast

An English Garden Bed & Breakfast

2 out of 5
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
St. Louis (STL) to Boston (BOS)

Top places to visit in Massachusetts

Boston Common featuring a monument, a city and a statue or sculpture
FlightsFlightsHotelsHotels

Boston

Boston

Flight deals to Massachusetts

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

Wed, May 29 - Tue, Jun 4
LAX
Los Angeles
BOS
Boston
$141 Roundtrip, found 3 days ago
$141
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, May 29 from Los Angeles to Boston, returning Tue, Jun 4, priced at $141 found 3 days ago
Tue, Jun 4 - Wed, Jun 5
PDX
Portland
BOS
Boston
$144 Roundtrip, found 3 days ago
$144
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Jun 4 from Portland to Boston, returning Wed, Jun 5, priced at $144 found 3 days ago
Mon, Jul 1 - Thu, Jul 4
LAX
Los Angeles
MVY
Vineyard Haven
$240 Roundtrip, found 6 days ago
$240
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Jul 1 from Los Angeles to Vineyard Haven, returning Thu, Jul 4, priced at $240 found 6 days ago

Top rated hotels for your Massachusetts vacation

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4.5 out of 5
450 Summer Street, Boston, MA
Free Cancellation
Reserve now, pay when you stay
17.82 mi from city center
The price is $214 per night
$214
per night
May 12 - May 13
With a stay at Omni Boston Hotel at the Seaport, you'll be centrally located in Boston, a 9-minute walk from Harpoon Brewery and 11 minutes by foot from Seaport Common.
Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
320 Washington Street, Newton, MA
10.56 mi from city center
The price is $147 per night
$147
per night
Jun 2 - Jun 3
Located in Newton (Newton Corner), Four Points by Sheraton Boston Newton is within a 10-minute drive of Boston University and Boston College.
Pool
Pet friendly
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street, Boston, MA
Free Cancellation
Reserve now, pay when you stay
17.14 mi from city center
The price is $191 per night
$191
per night
May 27 - May 28
With a stay at The Dagny Boston, you'll be centrally located in Boston, within a 10-minute walk of New England Aquarium and Faneuil Hall Marketplace.
Pet friendly
Breakfast available
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^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.