Search Deals onSoutheast Massachusetts Vacation Packages
Southeast Massachusetts Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Sunbird Cape Cod Resort
Save 100% on your flight
per person
May 5 - May 11
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hyannis Harbor and Cape Codder Water Park are located nearby.

Boston Lodge and Suites
Save 100% on your flight
per person
Jun 9 - Jun 12
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Boston Harbor Hotel
Save 100% on your flight
per person
May 22 - May 26
found 2 days ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Beacon Hill Hotel
Save 100% on your flight
per person
May 22 - May 26
found 2 days ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
Stay at this 4-star boutique hotel in Boston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and TD Garden are located nearby.

Concord's Colonial Inn
Save 100% on your flight
per person
May 5 - May 11
found 2 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star historic hotel in Concord. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Monument Square and Sleepy Hollow Cemetery are located nearby.

Mandarin Oriental, Boston
Save 100% on your flight
per person
Jun 18 - Jun 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.

Centerboard
Save 100% on your flight
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this hotel in Nantucket. Enjoy free WiFi, daily housekeeping, and cable TV channels. Popular attractions First Congregational Church and White Heron Theatre are located nearby.

Beachside Village Resort
Save 100% on your flight
per person
May 5 - May 11
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star beach apartment in Falmouth. Enjoy free WiFi, an outdoor pool, and daily housekeeping. Our guests praise the property condition in our reviews. Popular attractions Woods Hole Ferry Terminal and Surf Drive Beach are located nearby.
Southeast Massachusetts Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Southeast Massachusetts Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



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

Wed, May 7 - Tue, May 20
LAX
Los Angeles Intl.
BOS
Logan Intl.
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago

Sun, Aug 10 - Tue, Aug 19
PDX
Portland Intl.
BOS
Logan Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago

Tue, Jun 3 - Tue, Jun 10
PDX
Portland Intl.
PVD
T.F. Green
$255 Roundtrip, found 1 day ago
$255
Roundtrip
found 1 day ago

Tue, Apr 22 - Sat, Apr 26
LAX
Los Angeles Intl.
PVD
T.F. Green
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
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Car Rentals in Southeast Massachusetts
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