Westwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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 Harbor Hotel
Raffles Boston
Beacon Hill Hotel
The Beverly

Ready to book your vacation to Westwood?

 

Choose your dates

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
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

What to do 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.