Westwood Vacations from $736

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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.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
Seaport District
Save 100% on your flight
Price was $1,078, price is now $736 per person
$736
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (4,521 reviews)
My room had the bare minimum, no extra blankets no extra towels. One bathrobe, even though there was two of us stinging in the room. Our checkout check-in person did not ask us any questions regarding amenities. We might want in the room.. we found out later you need to ask for them, not even knowing what they were. I was small, which was which was fine, but being able to see into the toilet area with a glass door felt inappropriate.

Reviewed on Mar 9, 2026

The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Save 100% on your flight
Price was $1,320, price is now $837 per person
$837
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (2,398 reviews)
More workers at Starbucks during the Volleyball Tournament

Reviewed on Mar 3, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $4,560, price is now $3,066 per person
$3,066
per person
May 4 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return!

Reviewed on Mar 14, 2026

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Save 100% on your flight
Price was $1,358, price is now $927 per person
$927
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,266 reviews)
Wow!! Staff was amazing room was spotless, great location. Highly recommended. Will stay here again

Reviewed on Mar 13, 2026

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was $1,145, price is now $787 per person
$787
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (2,282 reviews)
Excellent location, walk to Museum of Fine Arts and more. Staff are very friendly, very clean. Beautiful large room. Glad I chose to stay and will be back.

Reviewed on Mar 14, 2026

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Discover the most popular places to visit in Westwood

Nighttime baseball game at Fenway Park showcasing a vibrant atmosphere in Boston, Massachusetts

Fenway Park

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

Fenway Park
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium
Boston Common showcases lush greenery and city skyline under a clear blue sky during a sunny day

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

Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
100% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
See all activities in Westwood

Westwood Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$187 nightly
The price is $218 total per night from Mar 22 to Mar 23
$218 total
Mar 22 - Mar 23
Total with taxes and fees
9.2/10 Wonderful! (4,513 reviews)
Employees wrre so very rude

Reviewed on Mar 15, 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
$182 nightly
The price is $212 total per night from Apr 5 to Apr 6
$212 total
Apr 5 - Apr 6
Total with taxes and fees
8.4/10 Very Good! (3,118 reviews)
Second stay here. This is now our go to hotel in Boston. Excellent staff, location, and wonderful lobby/lounge. Can’t wait to return.

Reviewed on Mar 13, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$169 nightly
The price is $197 total per night from Mar 20 to Mar 21
$197 total
Mar 20 - Mar 21
Total with taxes and fees
9.2/10 Wonderful! (6,364 reviews)
Only real complaint is that there is no coffee maker in room or in lobby. Have to pay for it in restaurant, which wouldn't be a problem if it was any good.

Reviewed on Mar 14, 2026

Harborside Inn Of Boston
See all 3,966 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.

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 $736 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.