Whitman Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.

Top Whitman Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The air conditioner sound like a truck trailer was in your room

Reviewed on Jul. 11, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Not bad at all, but nothing special

Reviewed on Jul. 13, 2025

Ready to book your vacation to Whitman?

 

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Whitman Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from Aug 10 to Aug 11
CA $289
CA $393 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (3,667 reviews)
"The hotel was clean and staff was friendly."

Reviewed on Jul. 12, 2025

Omni Boston Hotel at the Seaport
The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Jul 20 to Jul 21
CA $233
CA $271 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (2,069 reviews)
"Perfect place for family."

Reviewed on Jul. 10, 2025

The Revolution Hotel
The Westin Boston Seaport District
The Westin Boston Seaport District
4 out of 5
425 Summer St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jul 20 to Jul 21
CA $208
CA $290 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (2,012 reviews)
"Beautiful hotel, beds were so comfortable. We loved our stay."

Reviewed on Jul. 13, 2025

The Westin Boston Seaport District
See all 1,454 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Whitman

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(305 reviews)

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

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

4.5/5(279 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 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

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $96
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $46
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Whitman

Frequently asked questions

How much does a Whitman vacation package cost?
Offering great value package deals from CA $705 on Expedia, you'll be surprised at 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?
January, February and November are great times to search for cheap Whitman vacation packages. Travelling in less busy periods means you can generally find better prices on hotels and flights.
How many days is enough for Whitman?
For your Whitman vacation, a few days will be enough to tour the top spots. Make sure to check out Ames Nowell State Park --- it's one of the leading attractions in this destination. If you're looking for more activities, consider basing yourself here and venturing off on some tours from Whitman.
How to find the best Whitman package deals?
Finding a cheap Whitman package deal is a cinch with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Whitman package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Whitman vacation as a package?
You can enjoy significant savings on your next Whitman getaway by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Whitman?
If you're considering an impromptu Whitman vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Whitman?

  1. Choose when to get away: Check your schedule and get your bags packed. Your favourite season and the type of activities available will also help you decide when to visit Whitman.
  2. Set a budget: Consider expenses like transportation, flights and meals when working out how much to save for your trip to Whitman. Then, pick a hotel that works with your budget, whether that's an economical stay or a more upscale getaway.
  3. Set the duration of your trip: Start by making a list of all the activities and sights you want to experience in Whitman. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your accommodations and airfare: Once you've settled on your dates and duration, book the ideal Whitman vacation package for you.

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