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 Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,062, price is now CA $590 per person
CA $590
per person
Nov 1 - Nov 3
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was CA $1,563, price is now CA $1,038 per person
CA $1,038
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
Phil’s property is immaculate and the rooms are very clean and will all required amenities. Phil’s hospitality is also top notch and it will be my place to stay in my future cape cod visits!!

Reviewed on Aug. 20, 2025

Cambria Hotel & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Price was CA $994, price is now CA $679 per person
CA $679
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (18 reviews)
We’d love to come back here.

Reviewed on Aug. 22, 2025

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Price was CA $1,051, price is now CA $725 per person
CA $725
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8.4/10 Very Good! (319 reviews)
Great stay at an amazing locations. No issues we had a blast. They were so welcoming and inviting and the room was clean and comfortable.

Reviewed on Aug. 23, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was CA $1,545, price is now CA $1,078 per person
CA $1,078
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (585 reviews)
The location was great and we were able to get to all the sites easily. Also, liked having two beds and two bathrooms for the price. However, everything was very cheap in there. The sheets were nubbie because they were cheap and worn. The toliet paper was so awful we had to buy our own. The beds had little support. The place was clean though. So if you don't care much about the bed, sheets, and toliet paper it is a good pick. If you do maybe pick somewhere else.

Reviewed on Aug. 17, 2025

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Westwood Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
The price is CA $249 per night from Sep 1 to Sep 2
CA $249
CA $347 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,840 reviews)
"Overall a great hotel. Well located, the seaport zone is really beautiful. Public transportation access"

Reviewed on Aug. 21, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Sep 1 to Sep 2
CA $268
CA $312 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,680 reviews)
"I missed the 11:30pm train but thankfully Citizens is right next door. I was able to book the room and check in within 10 minutes. I was so happy with my room, I had an amazing view. Nice clean shower and space for a single person or couple. Will always stay at Citizens when I go to Boston now!"

Reviewed on Aug. 21, 2025

citizenM Boston North Station
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Sep 1 to Sep 2
CA $210
CA $252 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,259 reviews)
"We liked that the beds were comfortable and the AC was quiet. The food at the hotel was delicious. The pool was also very nice."

Reviewed on Aug. 22, 2025

Seaport Hotel Boston
See all 3,539 properties in Westwood
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Westwood

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes flowers, a garden and landscape views

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.

Boston Common

What to do in Westwood

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Westwood

Frequently asked questions

How much does a Westwood vacation package cost?
You'll find cheap prices from CA $590 on Expedia for your Westwood break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Westwood costs.
What are the cheapest months to go to Westwood?
If you'd like to book a cheap Westwood vacation package, consider planning a trip in February, September and December. You'll generally find better rates on accommodations and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Westwood?
Westwood vacations come in various shapes and sizes, but to really sink your teeth into this destination, we think 2 days is a good ballpark. This will mean you can visit top sights like Belkin Family Lookout Farm and Stony Brook Reservation and track down some hidden gems. Don't forget to explore neighbourhoods such as Hyde Park and West Roxbury either. If you're clever with your time, you can even take a day trip or two from Westwood too.
How to find the best Westwood package deals?
Use Expedia's handy filters to help you find some tempting Westwood package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Westwood package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Westwood vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Westwood vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Westwood?
If you're planning a spur-of-the-moment Westwood getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Westwood?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Westwood.
  2. Plan your budget wisely: In addition to the cost of your hotel, you should factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Westwood.
  3. Decide how long to go away for: Now that you're more familiar with Westwood, you can work out the right length of your vacation. Put together a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your accommodations and airfare: Once you've settled on your dates and duration, lock in the perfect Westwood vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.