Cheap Vacations in Massachusetts

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Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Boston Marriott Burlington

Boston Marriott Burlington

4 out of 5
Burlington Town Center
Price was $420, price is now $340 per person
$340
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,325, price is now $925 per person
$925
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
Wayfinder Newport

Wayfinder Newport

4 out of 5
Price was $798, price is now $565 per person
$565
per person
May 2 - May 6
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $829, price is now $624 per person
$624
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Attwater

The Attwater

3.5 out of 5
Top of the Hill
Price was $1,042, price is now $802 per person
$802
per person
May 2 - May 6
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
Club Wyndham Long Wharf

Club Wyndham Long Wharf

2.5 out of 5
Downtown Newport
Price was $1,122, price is now $868 per person
$868
per person
May 2 - May 6
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
Gilded

Gilded

3 out of 5
Top of the Hill
Price was $907, price is now $710 per person
$710
per person
May 2 - May 6
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was $982, price is now $790 per person
$790
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Hilton Garden Inn Foxborough Patriot Place

Hilton Garden Inn Foxborough Patriot Place

3 out of 5
Price was $541, price is now $441 per person
$441
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Cliffside Inn

Cliffside Inn

3.5 out of 5
Bellevue Avenue Historic District
Save 100% on your flight
Price was $1,718, price is now $1,403 per person
$1,403
per person
May 2 - May 6
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)

3-night Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Hotel & Suites Boston - Peabody by IHG

Holiday Inn Hotel & Suites Boston - Peabody by IHG

3 out of 5
Price was $359, price is now $305 per person
$305
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $1,565, price is now $1,019 per person
$1,019
per person
Apr 25 - Apr 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $1,773, price is now $1,229 per person
$1,229
per person
Apr 10 - Apr 13
found 1 day ago
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
Price was $829, price is now $624 per person
$624
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was $982, price is now $790 per person
$790
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Boston Marriott Burlington

Boston Marriott Burlington

4 out of 5
Price was $420, price is now $340 per person
$340
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Luxury Apartments by Hyatus Downtown Boston

Luxury Apartments by Hyatus Downtown Boston

4.5 out of 5
Save 100% on your flight
Price was $889, price is now $722 per person
$722
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Hilton Garden Inn Foxborough Patriot Place

Hilton Garden Inn Foxborough Patriot Place

3 out of 5
Price was $541, price is now $441 per person
$441
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Price was $513, price is now $420 per person
$420
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Price was $630, price is now $527 per person
$527
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Hyatus Luxury Residences Everett

Hyatus Luxury Residences Everett

4.5 out of 5
Save 100% on your flight
Price was $1,871, price is now $1,567 per person
$1,567
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to Boston (BOS)
DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Price was $555, price is now $472 per person
$472
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)

4-night Massachusetts vacations

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

Arcadian Hotel

3.5 out of 5
Price was $619, price is now $457 per person
$457
per person
Apr 13 - Apr 17
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Save 100% on your flight
Price was $1,180, price is now $740 per person
$740
per person
Apr 13 - Apr 17
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $2,776, price is now $1,789 per person
$1,789
per person
Apr 13 - Apr 17
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $2,443, price is now $1,694 per person
$1,694
per person
Apr 13 - Apr 17
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
Wayfinder Newport

Wayfinder Newport

4 out of 5
Price was $798, price is now $565 per person
$565
per person
May 2 - May 6
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Save 100% on your flight
Price was $1,063, price is now $756 per person
$756
per person
Apr 13 - Apr 17
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
The Dagny Boston

The Dagny Boston

4 out of 5
Save 100% on your flight
Price was $1,022, price is now $731 per person
$731
per person
Apr 13 - Apr 17
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
Omni Parker House

Omni Parker House

4.5 out of 5
Save 100% on your flight
Price was $1,147, price is now $835 per person
$835
per person
Apr 13 - Apr 17
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
Save 100% on your flight
Price was $949, price is now $694 per person
$694
per person
Apr 13 - Apr 17
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
Price was $770, price is now $569 per person
$569
per person
Apr 13 - Apr 17
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
The Attwater

The Attwater

3.5 out of 5
Price was $1,042, price is now $802 per person
$802
per person
May 2 - May 6
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Save 100% on your flight
Price was $1,074, price is now $830 per person
$830
per person
Apr 13 - Apr 17
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)

5-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
Price was $929, price is now $824 per person
$824
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $3,095, price is now $2,107 per person
$2,107
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $2,762, price is now $2,012 per person
$2,012
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Price was $1,381, price is now $1,074 per person
$1,074
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Omni Parker House

Omni Parker House

4.5 out of 5
Price was $1,466, price is now $1,154 per person
$1,154
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Price was $1,393, price is now $1,129 per person
$1,129
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
The Dagny Boston

The Dagny Boston

4 out of 5
Price was $1,341, price is now $1,149 per person
$1,149
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Luxury Apartments by Hyatus Downtown Boston

Luxury Apartments by Hyatus Downtown Boston

4.5 out of 5
Price was $1,312, price is now $1,128 per person
$1,128
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Price was $1,343, price is now $1,158 per person
$1,158
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
The Newbury Boston

The Newbury Boston

5 out of 5
Price was $2,441, price is now $2,139 per person
$2,139
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Price was $1,333, price is now $1,187 per person
$1,187
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
Price was $1,268, price is now $1,129 per person
$1,129
per person
Apr 13 - Apr 17
found 11 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)

6-7 night Massachusetts vacations

Price found within the past 48 hours. Click for updated prices.
Motel 6 Nashua, NH - North

Motel 6 Nashua, NH - North

2 out of 5
Price was $775, price is now $693 per person
$693
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Centennial

The Centennial

4 out of 5
Save 100% on your flight
Price was $1,438, price is now $1,029 per person
$1,029
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Manchester (MHT)
The Artisan At Tuscan Village, Salem, A Tribute Portfolio Hotel

The Artisan At Tuscan Village, Salem, A Tribute Portfolio Hotel

4.5 out of 5
Price was $1,922, price is now $1,543 per person
$1,543
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Methuen Inn and Conference Center

Methuen Inn and Conference Center

2.5 out of 5
Price was $1,016, price is now $818 per person
$818
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was $1,861, price is now $1,575 per person
$1,575
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Manchester (MHT)
Tru by Hilton Manchester Downtown

Tru by Hilton Manchester Downtown

2.5 out of 5
Price was $1,153, price is now $988 per person
$988
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Ash Street Inn

Ash Street Inn

2 out of 5
Price was $1,523, price is now $1,316 per person
$1,316
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Lakeside Inn

Lakeside Inn

2 out of 5
Price was $1,041, price is now $900 per person
$900
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston

3 out of 5
Price was $1,075, price is now $940 per person
$940
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
Price was $1,894, price is now $1,667 per person
$1,667
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Holiday Inn Express Hotel & Suites Manchester Airport by IHG

Holiday Inn Express Hotel & Suites Manchester Airport by IHG

2.5 out of 5
Price was $1,268, price is now $1,123 per person
$1,123
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Holiday Inn Salem - I-93 at Exit 2 by IHG

Holiday Inn Salem - I-93 at Exit 2 by IHG

3 out of 5
Price was $1,043, price is now $935 per person
$935
per person
May 1 - May 8
found 10 hours ago
Roundtrip flight included
Chicago (ORD) 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.

Mon, Apr 27 - Thu, Apr 30
PDX
Portland
BOS
Boston
$204 Roundtrip, found 3 days ago
$204
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Apr 27 from Portland to Boston, returning Thu, Apr 30, priced at $204 found 3 days ago
Fri, Aug 21 - Sat, Aug 22
LAX
Los Angeles
PVD
Providence
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 21 from Los Angeles to Providence, returning Sat, Aug 22, priced at $206 found 1 day ago
Tue, Apr 21 - Sat, Apr 25
LAX
Los Angeles
BOS
Boston
$215 Roundtrip, found 12 hours ago
$215
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Tue, Apr 21 from Los Angeles to Boston, returning Sat, Apr 25, priced at $215 found 12 hours ago

Top rated hotels for your Massachusetts vacation

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Free Cancellation
Reserve now, pay when you stay
16.41 mi from city center
$157 nightly
The price is $183 total per night
$183 total
Mar 22 - Mar 23
Total with taxes and fees
With a stay at Hilton Boston Park Plaza, you'll be centrally located in Boston, steps from Boston Public Garden and within a 5-minute walk of Newbury Street.
Pet friendly
Free WiFi
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
17.14 mi from city center
$169 nightly
The price is $197 total per night
$197 total
Mar 10 - Mar 11
Total with taxes and fees
With a stay at Harborside Inn Of Boston, you'll be centrally located in Boston, steps from Faneuil Hall Marketplace and Quincy Market.
Free WiFi
Restaurant
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Free Cancellation
Reserve now, pay when you stay
17.86 mi from city center
$191 nightly
The price is $221 total per night
$221 total
Mar 22 - Mar 23
Total with taxes and fees
Located in Boston (Seaport District), Seaport Hotel Boston is a 3-minute walk from Liberty Wharf and 8 minutes by foot from Institute of Contemporary Art.
Pool
Pet friendly
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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.