Dorchester Vacation Packages

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    Save up to CA $1,096 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.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,479, price is now CA $1,673 per person
CA $1,673
per person
Jun 13 - Jun 17
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,353, price is now CA $2,072 per person
CA $2,072
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.

Reviewed on Mar 23, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,513, price is now CA $1,704 per person
CA $1,704
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
clean room. friendly and helpful staff. good breakfast in reasonable price. hope they have a boutique store to sell Langham signature products, especially the home fragrance products.

Reviewed on Mar 29, 2026

Summer House Hotel

Summer House Hotel

2 out of 5
Price was CA $2,516, price is now CA $1,771 per person
CA $1,771
per person
Jun 18 - Jun 21
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
No reviews
Life House, Nantucket

Life House, Nantucket

3.5 out of 5
Nantucket Town
Price was CA $2,833, price is now CA $2,033 per person
CA $2,033
per person
Jun 18 - Jun 21
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (65 reviews)
The Life House was a very quiet, charming and friendly spot. Very much so a boutique hotel feel. The only thing that wasn’t ideal was the room we stayed in on the 3rd floor. Being over 6 feet, the room had slanted ceilings and a very tight doorway. It was very tight and not spacious unlike some of the other rooms I saw. Would definitely stay again but would make sure I don’t stay in that room again.

Reviewed on Sep 26, 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

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

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 $132 per night from Apr 6 to Apr 7
CA $132
CA $154 total
Apr 6 - Apr 7
includes taxes & fees
6.8/10 (1,667 reviews)
We informed the front desk to send housekeeping for cleaning the room in the morning while leaving but no one came. Service is bad.

Reviewed on Mar 31, 2026

Ramada by Wyndham Boston
Home2 Suites by Hilton Boston South Bay

Home2 Suites by Hilton Boston South Bay

3 out of 5
15 JAN KARSKI WAY Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Apr 5 to Apr 6
CA $222
CA $259 total
Apr 5 - Apr 6
includes taxes & fees
8.8/10 Excellent! (991 reviews)
The rooms are very nice and clean. Breakfast was great. Staff was extremely friendly and helpful. Only issue I had was there is no parking for the hotel at the hotel. And we had to pay $25 a day to be able to park with the hotel.

Reviewed on Apr 1, 2026

Home2 Suites by Hilton Boston South Bay
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $214 per night from Apr 5 to Apr 6
CA $214
CA $306 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (4,549 reviews)
Very nice

Reviewed on Mar 28, 2026

Omni Boston Hotel at the Seaport
See all 4,225 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 $1,673, 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 $72
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
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

CA $32
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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.