Westwood Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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
Dorchester
CA $811
per person
Oct 21 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Fairmont Copley Plaza, Boston
Back Bay
CA $1,579
per person
Sep 30 - Oct 3
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9/10 Wonderful! (1,316 reviews)
Beautiful hotel excellent location very helpful staff Highly recommend for your next trip to Boston
Reviewed on Aug 27, 2026
Ready to book your vacation to Westwood?
Westwood Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $263
CA $354 total
Sep 7 - Sep 8
includes taxes & fees
9.6/10 Exceptional! (4,873 reviews)
"Great location. Safe and clean. Perfect view of the harbor. Only complaint is they need to lose the automated phone call line when trying to reach the bellman or front desk. Called for bags using their robot and it never connected to a live human. Human touch is key in customer service. So lose the ..."
Reviewed on Aug 27, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $179
CA $208 total
Aug 30 - Aug 31
includes taxes & fees
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $304
CA $410 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (4,808 reviews)
"Great hotel!"
Reviewed on Aug 27, 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.
Stay near popular Westwood attractions
Brigham and Women's Health Care Center, Westwood
Though Brigham and Women's Health Care Center, Westwood might be what brings you to town, perhaps you'll have a chance to explore more of Westwood while you are here.
What to do in Westwood
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
per adult
80% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $118
per adult
92% of travellers recommend
Frequently asked questions
How much does a Westwood vacation package cost?
You'll find cheap prices from CA $811 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?
- 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.
- 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.
- 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.
- Bundle your accommodations and airfare: Once you've settled on your dates and duration, lock in the perfect Westwood vacation package for you.
Explore a world of travel with Expedia
- Hotels near Fenway Park
- Motels in Boston
- Boston Hotels
- Norwood Hotels
- Downtown Boston Hotels
- Cheap Hotels in Boston
- Seaport District Hotels
- Inns in Westwood
- B&B in Norwood
- Beacon Hill Hotels
- Cambridge Hotels
- Hotels near Boston College
- Hotels near Flynn Cruiseport Boston
- Hotels near Gillette Stadium
- Hotels near TD Garden
- Back Bay Hotels
- Beach Hotel Hotels in Westwood
- Hotels near Logan Intl.
- Holiday Inn Express & Suites Norwood
- B&B in Boston
- Family Vacation Modern Norwood
- Hotels near Boston Common
- Westwood Hotels
- Hotels with Free Airport Shuttle in Boston
- Hotels near Boston Convention and Exhibition Center
- Hotels near Boston Harbor
- Hotels with a Pool in Boston
- Hotels near Harvard University
- Salem Hotels
- Villas in Westwood
- Hotels with Free Parking in Boston
- Flights from Victoria (YYJ) to Boston (BOS)
- Flights from New York (NYC) to Boston (BOS)
- Flights from Toronto (YYZ) to Boston (BOS)
- Flights from Buffalo (BUF) to Boston (BOS)
- Flights from Moncton (YQM) to Boston (BOS)
- Flights from Ottawa (YOW) to Boston (BOS)
- Flights from Vancouver (YVR) to Boston (BOS)
- Flights from Montreal (YUL) to Boston (BOS)
- Flights to Norwood
- Flights from Winnipeg (YWG) to Boston (BOS)
- Flights from Saskatoon (YXE) to Boston (BOS)
- Flights from Regina (YQR) to Boston (BOS)
- Flights from Chicago (ORD) to Boston (BOS)
- Flights to Westwood
- Flights from Calgary (YYC) to Boston (BOS)
- Flights from Seattle (SEA) to Boston (BOS)
- Flights to Salem
- Air Canada Toronto (YYZ) to Boston (BOS) flights
- Flights from Toronto (YTZ) to Boston (BOS)
- Porter Airlines Toronto (YTZ) to Boston (BOS) flights
- Flights from Detroit (DTW) to Boston (BOS)
- Flights from Logan Intl.
- Flights from London (YXU) to Boston (BOS)
- Flights from Halifax (YHZ) to Boston (BOS)
- Flights from Edmonton (YEG) to Boston (BOS)
- Flights to Boston
- Flights to Massachusetts
- Flights from Hamilton (YHM) to Boston (BOS)
- Visit Massachusetts
- Boston Tea Party Ship
- Gillette Stadium
- Copley Square
- Boston Public Garden
- Revere Beach
- Visit Seaport District
- Td Garden
- Visit Beacon Hill
- Berklee College of Music
- Massachusetts State House
- Boston Museum of Fine Arts
- Quincy Market
- All inclusive Vacation Packages Boston
- St. Elizabeth's Medical Center
- Fenway Park
- Boston Common
- Harvard University
- Boston Vacations
- Waterfront Vacations
- Prudential Tower
- The Freedom Trail
- Isabella Stewart Gardner Museum
- Visit Downtown Boston
- Charles River Esplanade
- Salem Vacations
- Visit Boston
- Newbury Street
- Zakim Bunker Hill Bridge
- New England Aquarium
- Massachusetts Institute of Technology
- Arnold Arboretum
- Boston Harbor
- Boston Marathon Finish Line
- Museum of Science
- Faneuil Hall Marketplace
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
