Westwood Vacations from $621

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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.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Save 100% on your flight
Price was $929, price is now $621 per person
$621
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (1,451 reviews)
Room was so small you could barely turn around. If it’s just you prob ok. Two barley fit. Super noisy in our room. Outside house. AC was very loud. Woke us up multiple times during the night.

Reviewed on May 28, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $3,397, price is now $1,679 per person
$1,679
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again

Reviewed on May 25, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $2,045, price is now $1,173 per person
$1,173
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Staff was very nice and helpful.

Reviewed on May 28, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $5,529, price is now $3,526 per person
$3,526
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (685 reviews)
Do yourself a favor and stay here the rooms are not incredibly updated, but they are incredibly clean and well-maintained and the overall aesthetic of the place is top shelf, but the glowing star of the entire place are the Jamaican staff that run the place you will not find nicer people that are more accommodating and friendly not to mention the café is a 10 out of 10 highly recommend this place also lots of parking

Reviewed on May 28, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,693, price is now $1,127 per person
$1,127
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (1,486 reviews)
Hotel was clean and kept in excellent condition, with helpful and friendly staff. Perfect place to stay for a city break and couldn't recommend it enough.

Reviewed on May 28, 2026

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Discover the most popular places to visit in Westwood

Fenway Park

Fenway Park

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

Fenway Park
Gillette 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
Harvard University

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

$84
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
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Harvard Guide leading a tour

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
See all activities in Westwood

Westwood Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
$244 nightly
The price is $284 total per night from May 31 to Jun 1
$284 total
May 31 - Jun 1
Total with taxes and fees
9.6/10 Exceptional! (4,385 reviews)
"Amazing hotel. Loved the fitness area."

Reviewed on May 30, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $177 total per night from Jun 7 to Jun 8
$177 total
Jun 7 - Jun 8
Total with taxes and fees
9/10 Wonderful! (2,635 reviews)
"Loved it so much I came back for a second stay"

Reviewed on May 30, 2026

The Revolution Hotel
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
$258 nightly
The price is $301 total per night from Jun 7 to Jun 8
$301 total
Jun 7 - Jun 8
Total with taxes and fees
9.2/10 Wonderful! (4,655 reviews)
"My family and I stayed for two nights and it was absolutely incredible. One of the nicest hotels we've ever stayed in. Everything from the service to the food and the room of course were perfect! We had an incredible view of the city from our 18th floor room. That pool and hot tub especially were ..."

Reviewed on May 29, 2026

Omni Boston Hotel at the Seaport
See all 3,932 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 $621 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.

Explore a world of travel with Expedia

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