Westwood Vacation Packages
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Your Westwood Vacation
With all your travel plans worked out before you go, our Westwood vacation packages let you simply focus on vacationing! One neighborhood to base yourself in this exciting city is Dorchester, which is good for nature and dining. If sightseeing is on the cards during your trip to Westwood, look around popular attractions like Blue Hills Ski Area, Museum of American Bird Art at Mass Audubon and Eleanor Cabot Bradley Estate. Stop dreaming and start adventuring. Check out the range of options on Expedia today and finally put your Westwood vacation plans into gear!
Top Westwood Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Cove At Yarmouth
Price was CA $1,081, price is now CA $750 per person
CA $750
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (243 reviews)
Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time.
Reviewed on Jan 31, 2026
Boston Lodge and Suites
Dorchester
Price was CA $1,226, price is now CA $764 per person
CA $764
per person
Mar 30 - Apr 1
found 4 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
8.4/10 Very Good! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.
Reviewed on Nov 10, 2025
Encore Boston Harbor
Price was CA $1,737, price is now CA $1,194 per person
CA $1,194
per person
Apr 27 - May 1
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (3,386 reviews)
Gorgeous room with a view but the controller iPad can be a bit tricky to work and we couldn’t pair our phone to play music . Espresso coffee pods and extra bottles of water are a great touch. We ate at Mystique for my hubbys birthday and the food was fantastic. Overall a great stay here as always .
Reviewed on Feb 23, 2026
Studio Allston Hotel
Brighton
Price was CA $1,597, price is now CA $1,110 per person
CA $1,110
per person
May 2 - May 8
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (1,175 reviews)
Room had basics. Bed was stiff and there was a sharp metal frame that I cut my leg on. The exterior patio appeared unmaintained but looked cool.
Reviewed on Feb 22, 2026
Westwood Hotel Deals
Hilton Boston Park Plaza
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Mar 8 to Mar 9
CA $167
CA $251 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (3,139 reviews)
good
Reviewed on Feb 24, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Mar 1 to Mar 2
CA $157
CA $239 total
Mar 1 - Mar 2
includes taxes & fees
9.2/10 Wonderful! (4,501 reviews)
The room was spotless. The registration staff was very nice and professional. Quick service, checking in and out. The curbside staff was excellent, especially in the hot weather. They get top billing for the extraordinary efforts they made. Great hotel.
Reviewed on Feb 23, 2026
Harborside Inn Of Boston
185 State St Boston MA
The price is CA $134 per night from Mar 1 to Mar 2
CA $134
CA $156 total
Mar 1 - Mar 2
includes taxes & fees
9.2/10 Wonderful! (6,322 reviews)
It was a great stay
Reviewed on Feb 24, 2026
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.
Discover the most popular places to visit in Westwood
Fenway Park
4.5/5(305 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Gillette Stadium
4.5/5(27 reviews)
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.
Boston Common
4.5/5(518 reviews)
The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.
What to do in Westwood
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $108
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
CA $31
per adult
92% of travellers recommend
Explore a world of travel with Expedia
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- Arnold Arboretum
- Avon Vacations
- Berklee College of Music
- Boston College
- Boston Medical Center
- Boston Museum of Fine Arts
- Brookline Vacations
- Children's Hospital Boston
- Commonwealth Avenue Mall
- Dana-Farber Cancer Institute
- Fenway Park
- Foxboro Vacations
- Foxborough Country Club
- Franklin Park Zoo
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- Hall at Patriot Place
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- Hynes Convention Center
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- Visit Norwood
- Paradise Rock Club
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- The Shops at Prudential Center
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- Wollaston Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
