Dorchester Vacation Packages

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Top Holiday Package Deals in Dorchester

Price found within the past 48 hours. Click for updated prices.
Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Location was perfect.

Reviewed on Jul. 29, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on Jul. 28, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (349 reviews)
This experience from checking in to the quality of the room and the incredible concierge service that helped us with restaurants in our entire experience was unbelievable! It was probably the best experience I had with a luxury hotel in any city I visited. We will definitely be coming back!

Reviewed on Jul. 20, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
very comfortable suite, lovely staff, great breakfast area

Reviewed on Jul. 25, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
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Reviewed on Jul. 28, 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 $155 per night from Aug 17 to Aug 18
CA $155
CA $181 total
Aug 17 - Aug 18
includes taxes & fees
6.6/10 (1,287 reviews)
"Good"

Reviewed on Jul. 29, 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 $215 per night from Aug 11 to Aug 12
CA $215
CA $251 total
Aug 11 - Aug 12
includes taxes & fees
8.2/10 Very Good! (1,360 reviews)
Proximity to T line
"We enjoyed our stay at your hotel. We especially loved the proximity to the T line. Your cookies were delicious too! Thanks!"

Reviewed on Jul. 27, 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 $210 per night from Aug 24 to Aug 25
CA $210
CA $244 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"IT WAS CLEAN"

Reviewed on Jul. 28, 2025

Courtyard by Marriott Boston-South Boston
See all 3,888 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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Dorchester vacation package cost?
Maybe less than you might think — from only CA $1,040, 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

Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace

Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace

CA $14
per traveller
84% of travellers recommend
Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace
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
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.