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
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 12 - Sep 15
found 2 days ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Amazing stay - the location is perfect and the people who work there make all the difference!

Reviewed on Aug. 9, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 12 - Sep 15
found 2 days ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on Aug. 5, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul. 17, 2025

The Beverly

The Beverly

3 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (323 reviews)
Location was very good. Overall our stay was very good. The only issue is that if you are not careful to place the shower curtain inside the tub the floor gets all wet. The bathroom floor was all wet when we got there

Reviewed on Aug. 8, 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
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Aug 24 to Aug 25
CA $252
CA $350 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,784 reviews)
Decent Size Studio Rm, can get noisy from planes
"I stayed at the Artist Studio Tower, which faces the East and North I think. The room itself was thoughtfully designed to utilize limited space for comfort, and looked nice and luxurious. However, there wasn't any dedicated desk for working on a laptop (Just a small stand for a coffee machine and ..."

Reviewed on Aug. 7, 2025

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Sep 1 to Sep 2
CA $221
CA $313 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (3,193 reviews)
"Rooms are very dated but the location is exceptional!"

Reviewed on Aug. 6, 2025

Hilton Boston Park Plaza
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $267 per night from Aug 17 to Aug 18
CA $267
CA $311 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (1,584 reviews)
"good location and friendly service"

Reviewed on Aug. 10, 2025

citizenM Boston Back Bay
See all 3,514 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 $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $75
per adult
86% 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 $756 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.