Dorchester Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Dorchester

Price found within the past 48 hours. Click for updated prices.
Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Price was CA $1,223, price is now CA $899 per person
CA $899
per person
Jul 30 - Aug 3
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.8/10 Good! (826 reviews)
Had a few bumps in my stay but overall was great! My son loves the playground and we were given 2 night stay for free in the future. Staff is always nice!

Reviewed on May 4, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,665, price is now CA $1,057 per person
CA $1,057
per person
Jul 30 - Aug 3
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $3,227, price is now CA $2,056 per person
CA $2,056
per person
Jul 11 - Jul 17
found 9 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (255 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,342, price is now CA $2,831 per person
CA $2,831
per person
Jul 24 - Jul 29
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
clean and great staff

Reviewed on May 8, 2026

Cambridge Common House

Cambridge Common House

4 out of 5
West Cambridge
Price was CA $1,746, price is now CA $1,262 per person
CA $1,262
per person
Jul 22 - Jul 26
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
10/10 Exceptional! (2 reviews)
Everything in this hotel is excellent! The bedding is very comfortable. Stuff is great! The place is so cozy and quiet, with very nice decor that gives a relaxed feel. Amazing atmosphere, if you like privacy and quiet. Everything you need is within walking distance. Highly recommend.

Reviewed on May 3, 2026

Where to stay in Dorchester

Find the best Dorchester areas and neighborhoods for the activities you enjoy most. Learn more about Dorchester
Downtown Boston

Downtown Boston

4.5/5(197 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

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 $179 per night from May 25 to May 26
CA $179
CA $209 total
May 25 - May 26
includes taxes & fees
8.4/10 Very Good! (1,473 reviews)
Friendly staff

Reviewed on May 18, 2026

DoubleTree by Hilton Hotel Boston Bayside
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 $186 per night from May 25 to May 26
CA $186
CA $216 total
May 25 - May 26
includes taxes & fees
6.8/10 (1,727 reviews)
Staff was very friendly and courteous...breakfast was good..but room could have been a bit better. Overall a 3 for budget friendly.

Reviewed on May 17, 2026

Ramada by Wyndham Boston
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $318 per night from May 25 to May 26
CA $318
CA $418 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (4,357 reviews)
I didn’t have breakfast.

Reviewed on May 17, 2026

Seaport Hotel Boston
See all 4,332 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 $899, 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 Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $79
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $115
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
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.