Whitman Vacations from $574

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Your Whitman Vacation

Art, food, entertainment and more … It's all waiting for you with a Whitman vacation package. And with the ability to easily customize your city getaway, it's guaranteed to be one that's tough to forget. If your trip to Whitman includes a little sightseeing, hit up famous attractions like Rockland Ice Rink, Campanelli Stadium and Rockland Golf Course. Expedia is here to help you escape your daily routine. Tailor your vacation to Whitman to match your travel style, whatever that may be.

The Latest Whitman vacation packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $900, price is now $574 per person
$574
per person
May 14 - May 16
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.6/10 Excellent! (1,384 reviews)
Good location to T.D. Garden.

Reviewed on Mar 7, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,402, price is now $906 per person
$906
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

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,096, price is now $749 per person
$749
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Friendly staff, clean room

Reviewed on Feb 20, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,824, price is now $1,252 per person
$1,252
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,666, price is now $1,177 per person
$1,177
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room and staff were great

Reviewed on Feb 26, 2026

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Discover the most popular places to visit in Whitman

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

Fenway Park

4.5/5(2,499 reviews)

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

4.5/5(388 reviews)

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

4.5/5(4,786 reviews)

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 Whitman

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 Whitman

Whitman Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $221 total per night from Mar 22 to Mar 23
$221 total
Mar 22 - Mar 23
Total with taxes and fees
9.6/10 Exceptional! (4,053 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
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $128 total per night from Mar 30 to Mar 31
$128 total
Mar 30 - Mar 31
Total with taxes and fees
9/10 Wonderful! (2,535 reviews)
Room wasn’t ready at checkin after check in time, and coffee shop was opened late. Otherwise, clean, efficient stay in a great location

Reviewed on Mar 9, 2026

The Revolution Hotel
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

2 out of 5
220 Huntington Avenue Boston MA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $162 total per night from Mar 11 to Mar 12
$162 total
Mar 11 - Mar 12
Total with taxes and fees
7.6/10 Good! (1,020 reviews)
It is in the middle of the City and convenient to everything. Staff was very friendly and professional. It is an older hotel but very clean.

Reviewed on Mar 9, 2026

The Midtown Hotel MOD Collection by Sonesta
See all 1,628 properties in Whitman
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 Whitman Vacation Packages

Whitman Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
14,500
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Blue Hills Reservation, Wompatuck State Park and Wessagusset Beach

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Frequently asked questions

How much does a Whitman vacation package cost?
Offering great value package deals from $574 on Expedia, you'll be thrilled with how little a vacation to Whitman costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Whitman?
November, December and January are the best times to look for cheap Whitman vacation packages. Opting to travel in quieter periods means you can typically find better prices on flights and accommodations.
How many days is enough for Whitman?
Generally, a handful of days is enough to see the top sights during your Whitman vacation. However, if you'd like to have time to chill out or go on day tours, think about extending your trip.
How to find the best Whitman package deals?
Begin your search for a Whitman package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Whitman package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Whitman adventure underway.
Is it cheaper to book a Whitman vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Whitman vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Whitman?
Score fantastic discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Whitman getaway.
Does Expedia offer Book Now, Pay Later Whitman vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Whitman trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.

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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.