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.
Boston Harbor Hotel
North End
Price was CA $7,457, price is now CA $4,176 per person
CA $4,176
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.
Reviewed on Jan 25, 2026
Studio Allston Hotel
Brighton
Price was CA $2,299, price is now CA $1,393 per person
CA $1,393
per person
May 10 - May 17
found 1 day ago
Roundtrip 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 $250 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (3,135 reviews)
The rooms were very nice and the staff was helpful
Reviewed on Feb 22, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
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! (4,500 reviews)
The hotel is lovely and modern and filled with beautiful art and even contemporary furniture. However our art tower room was so small there was no bathroom, just a small enclosed toilet and small, separately enclosed shower. No room for a bathroom sink, which was located in the bedroom! No closet ...
Reviewed on Feb 22, 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! (6,316 reviews)
Very clean and spacious room
Reviewed on Feb 23, 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
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Gillette Stadium
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.
Boston Common
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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- Flights to Norwood
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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
- Gillette Stadium
- Hall at Patriot Place
- Harvard University
- Holliston Vacations
- Hynes Convention Center
- Isabella Stewart Gardner Museum
- Legacy Place
- Newton Vacations
- Norwood Vacations
- Visit Norwood
- Paradise Rock Club
- Prudential Tower
- St. Elizabeth's Medical Center
- The Shops at Prudential Center
- Waban Vacations
- Waltham Vacations
- Wollaston Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
