Westwood Vacations from $311

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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!

The Latest Westwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

2 out of 5
Coolidge Corner South Side
Save 100% on your flight
Price was $551, price is now $311 per person
$311
per person
Dec 31 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
16.8/10 Exceptional! (268 reviews)
The kitchen isn't fully equipped for cooking. I found some culinary utensils incl. a pan and a pot. But there wasn't any stove to cook. The shops nearby are great incl. Trader Joe's and Maruichi.

Reviewed on Nov 4, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,147, price is now $470 per person
$470
per person
Jan 29 - Feb 2
found 24 hours ago
Roundtrip flight included
Los Angeles (QLA) to Boston (BOS)
16.8/10 Exceptional! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
Newton Corner
Save 100% on your flight
Price was $641, price is now $350 per person
$350
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
16.8/10 Exceptional! (2,907 reviews)
Staff that checked us in was very welcoming

Reviewed on Nov 20, 2025

Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner South Side
Save 100% on your flight
Price was $1,189, price is now $667 per person
$667
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
18.8/10 Exceptional! (460 reviews)
The entire experience at The Iris hotel was excellent form the Valet parking, the room, the bar & the restaurant. I would stay there anytime I'm in Brookline

Reviewed on Nov 22, 2025

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2 out of 5
Beacon Hill
Save 100% on your flight
Price was $587, price is now $330 per person
$330
per person
Dec 31 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
15.2/10 Exceptional! (102 reviews)
Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌

Reviewed on Oct 27, 2025

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Discover the most popular places to visit in Westwood

Fenway Park which includes 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
Boston Common featuring landscape views, a skyscraper and flowers

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
Harvard University showing 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

What to do in Westwood

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Hear the legendary true stories of Revolutionary Bostonians like Paul Revere, Midnight Rider at the Old North Church

Boston: Freedom Trail History Small Group Walking Tour

$39
per adult
100% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$54
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
See all activities in Westwood

Find the Best Westwood Vacation Packages

Westwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
14,000
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Boston Museum of Fine Arts, Isabella Stewart Gardner Museum and John F. Kennedy Presidential Library and Museum

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Frequently asked questions

How much does a Westwood vacation package cost?
You can pick up a vacation package to this popular destination from $311 on Expedia. However, how much your vacation to Westwood costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Westwood?
If you're hoping to snag a cheap Westwood vacation package, consider visiting in July, September and October. You're likely to find better rates on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Westwood?
Typically, a handful of days is enough to explore the top attractions during your Westwood vacation. However, if you prefer to have some time to unwind or go on day trips, think about extending your itinerary.
How to find the best Westwood package deals?
Start your search for a Westwood package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Westwood package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Westwood escape off to a flying start.
Is it cheaper to book a Westwood vacation as a package?
You can enjoy significant savings on your Westwood retreat by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Westwood?
Score incredible discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Westwood getaway.
Does Expedia offer Book Now, Pay Later Westwood vacation packages?
Secure your dream getaway to Westwood with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next paycheck — we've teamed up with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stay on budget and snap up travel deals while they last.

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