Dorchester Vacation Packages

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Top Holiday Package Deals in Dorchester

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

The Beverly

3 out of 5
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (323 reviews)
Stopped in for overnight stay. Awkward check in as no emailed code (no desk staff on premises), got that worked out. Rooms are comfortable and appeared clean. Couple of places across street to eat and little shopping center, so nice options for quick stay.

Reviewed on Jul. 31, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
Sep 7 - Sep 10
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (234 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul. 17, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Sep 7 - Sep 10
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (3,159 reviews)
This was one of our best stays by far on our 30 day road trip in July. Our room was beautiful overlooking the Boston Harbor which was a romantic view at night. We deeply appreciated the convenience of the high-tech set up allowing us to control everything on an iPad. That was a unique experience and one I wish all hotels utilized. The bathtub is a great soaking tub with a TV on the wall and there’s even a place to rest your arms. The shower was nice too. The room was a large size compared to most hotel rooms.

Reviewed on Aug. 2, 2025

Hyatt Regency Boston

Hyatt Regency Boston

4 out of 5
Downtown Boston
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (1,577 reviews)
Stayed here for 1 night . It’s a clean quiet and walkable to the highlights of Boston downtown .

Reviewed on Aug. 3, 2025

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
Pool was closed. Amenities are included in price. No discount. Asked front counter. Front desk staff member was curt when I brought this up. Room was clean and the mini Starbucks was a plus. The hotel was dated and could use some updates. It would also be helpful to move the smoking area away from the front entrance.

Reviewed on Aug. 3, 2025

Where to stay in Dorchester

Find the best Dorchester areas and neighborhoods for the activities you enjoy most. Learn more about Dorchester
Downtown Boston showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(193 area reviews)

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

Find hotels in Downtown Boston

Dorchester Hotel Deals

Ramada by Wyndham Boston

Ramada by Wyndham Boston

2.5 out of 5
800 Morrissey Blvd, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Sep 3 to Sep 4
CA $154
CA $180 total
Sep 3 - Sep 4
includes taxes & fees
6.6/10 (1,291 reviews)
"it is very nice hotle and safty."

Reviewed on Jul. 30, 2025

Ramada by Wyndham Boston
DoubleTree by Hilton Hotel Boston Bayside

DoubleTree by Hilton Hotel Boston Bayside

4 out of 5
240 Mount Vernon Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Aug 17 to Aug 18
CA $186
CA $217 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (1,352 reviews)
"Great location for quick access to Logan airport."

Reviewed on Jul. 31, 2025

DoubleTree by Hilton Hotel Boston Bayside
Courtyard by Marriott Boston-South Boston

Courtyard by Marriott Boston-South Boston

3 out of 5
63 R Boston St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Sep 1 to Sep 2
CA $208
CA $243 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)

Reviewed on Jul. 31, 2025

Courtyard by Marriott Boston-South Boston
See all 3,882 properties in Dorchester
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.
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Frequently asked questions

How much does a Dorchester vacation package cost?
Maybe less than you might think — from only CA $637, actually! By combining flights, hotels and car rentals into your own custom-built travel package, your Dorchester escape is just clicks away.
How do I get a cheap travel package to Dorchester?
Our Dorchester vacation packages promise plenty of savings for the savvy explorer. For the best deals, simply bundle your flights, hotels and extras (including tours) into an affordable package. But great bargains are only the start of your next amazing adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotels globally to choose from. No matter your style or budget, there's a package that's perfect for you.
Where should I stay in Dorchester?
Vacationers come from all over the world to see Fenway Park and TD Garden in Dorchester. Stay within a stone's throw of these must-see attractions to make sightseeing easy.
What are the top hotels in Dorchester?
Lg Suite For Up To 6 Ppl/1 Floor and Home2 Suites by Hilton Boston South Bay are among the most well-known hotels in Dorchester. Why not take a look at the facilities and rates at each and then make up your mind?
How far in advance should I book my Dorchester vacation?
While not all air carriers advertise ticket prices early, you can normally look up international fares on Expedia up to 12 months in advance. This is the time when you'll bag some incredible deals. If you're booking late, you may still be in luck. Sometimes the cheapest prices become available a few weeks before departure.
What does an Expedia Dorchester travel package include?
You can select from any combination of rental cars, hotels and flights. Once you've made your booking, you can add some experiences and activities. Want to pick your fare class? That's also easy to do. The choice is yours when it comes to creating your ideal Dorchester escape.
What should I know before booking a Dorchester travel package?
Locking in all the parts of your vacation together is an excellent way to save. Bundle your car rentals, airfares and hotels into a convenient package. But it's not just hotels. Expedia features all sorts of properties, including vacation rentals such as beachfront villas and serviced residences. You've got choices galore!
Can I choose my airline with a Dorchester Expedia vacation package?
You can, and with over 550 airlines to select from throughout the world, you have loads of choice. Search the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Dorchester vacation package?
Your situation can change unexpectedly, so yes. You may be able to cancel or amend your Dorchester vacation package at no cost within 24 hours of booking. For bookings older than that, you can still make the necessary changes, but your car rental company, hotel or airline may charge a fee. Need more information? Check out our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Dorchester

John F. Kennedy Presidential Library and Museum

John F. Kennedy Presidential Library and Museum

You can study the exhibits at John F. Kennedy Presidential Library and Museum, a museum with a storied past, during your trip to Boston. Experience the fascinating museums or attend a sporting event in this vibrant area.

John F. Kennedy Presidential Library and Museum

Things to do

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
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

CA $115
per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.