Westwood Vacations from $595

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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.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was $852, price is now $595 per person
$595
per person
May 13 - May 17
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (253 reviews)
Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time.

Reviewed on Jan 31, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,681, price is now $988 per person
$988
per person
May 21 - May 25
found 10 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (251 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,420, price is now $927 per person
$927
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (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

Centerboard

Centerboard

2 out of 5
Nantucket Town
Save 100% on your flight
Price was $2,265, price is now $1,579 per person
$1,579
per person
May 29 - Jun 3
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (105 reviews)
Place was beautiful, will definitely go back again

Reviewed on Nov 12, 2025

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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

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $198 total per night from Mar 23 to Mar 24
$198 total
Mar 23 - Mar 24
Total with taxes and fees
8.4/10 Very Good! (3,136 reviews)
great location. lobby is very spacious and nice. there was always an elevator ready to go up. room was nice and spacious. no wardrobe. no view. the bathroom was old and lack shelves. we had an issue with hot water, it was most of the time slightly warm and not hot.

Reviewed on Mar 9, 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 12 to Mar 13
$197 total
Mar 12 - Mar 13
Total with taxes and fees
9.2/10 Wonderful! (6,339 reviews)
Have stayed here twice. First time was great. Second time shower was cold.

Reviewed on Mar 11, 2026

Harborside Inn Of Boston
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $191 total per night from Apr 5 to Apr 6
$191 total
Apr 5 - Apr 6
Total with taxes and fees
9.6/10 Exceptional! (4,056 reviews)
Beautiful hotel. Walking distance to shops and plenty of places to eat. Easy access to public transportation. No airport shuttle but you don’t need it. The public bus will take you there in less than 15 minutes

Reviewed on Mar 9, 2026

Seaport Hotel Boston
See all 3,959 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 $595 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.