Dorchester Vacation Packages

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Top Holiday Package Deals in Dorchester

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jun. 23 - Jun. 26
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.2/10 Wonderful! (27 reviews)
Very good service. Furniture in all areas and the room is low and petite. Not comfortable. Bedding is comfortable. Food on Long Bar was well prepared. However presentation is pedestrian. Ordered Avacado Toast. Tasty, but arrived on a small plate. No garnish, no fruit etc. overall good stay.

Reviewed on Apr. 8, 2024

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Jun. 23 - Jun. 26
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
i loved my room overlooking the park with gorgeous windows! just lovely.

Reviewed on Apr. 21, 2024

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
per person
Jul. 4 - Jul. 7
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.2/10 Very Good! (1,617 reviews)
Was great location. Rooms are very small

Reviewed on Apr. 22, 2024

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
per person
Jul. 4 - Jul. 7
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.6/10 Excellent! (1,448 reviews)
Restaurant menu needs further expansion

Reviewed on Apr. 23, 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Jun. 23 - Jun. 26
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (274 reviews)
My husband and I spent one night at The Whitney and were extremely pleased with our stay. The room was lovely and the staff were very nice and helpful. We would absolutely return and recommend it without hesitation.

Reviewed on Mar. 24, 2024

Prices and availability subject to change. Additional terms may apply.

Where to stay in Dorchester

Find the best Dorchester areas and neighborhoods for the activities you enjoy most. Learn more about Dorchester
Downtown Boston which includes night scenes and a city 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 hotel + flight trips 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 $171 per night from Apr. 28 to Apr. 29
CA $171
CA $199 total
includes taxes & fees
Apr 28 - Apr 29
8/10 Very Good! (1,005 reviews)
"The check in procedures was quick easy & was able to check in early with no problem & the staff member was very helpful with what do & what is he best & cheapest way to get around was"

Reviewed on Apr. 20, 2024

DoubleTree by Hilton Hotel Boston Bayside
Ramada by Wyndham Boston
Ramada by Wyndham Boston
2.5 out of 5
800 Morrissey Blvd, Boston, MA
The price is CA $184 per night from Apr. 24 to Apr. 25
CA $184
CA $214 total
includes taxes & fees
Apr 24 - Apr 25
6.6/10 (1,006 reviews)
"Good"

Reviewed on Apr. 19, 2024

Ramada by Wyndham Boston
Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $322 per night from May 24 to May 25
CA $322
CA $415 total
includes taxes & fees
May 24 - May 25
9/10 Wonderful! (1,977 reviews)
"Great property, king suite was very spacious, peekaboo water views bc they are building in tween the hotel and the harbor now, lots of restaurants, but lacked variety in food selections I feel, great bars and beverages. Staff was excellent, concierge, front desk, room service, bellman services, and ..."

Reviewed on Apr. 21, 2024

Omni Boston Hotel at the Seaport
See all 3,408 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Dorchester vacation package cost?
Maybe less than you might think — from only CA $900, 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

Image for John F. Kennedy Presidential Library and Museum

John F. Kennedy Presidential Library and Museum

4.5/5(2 reviews)

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 walkable area.

John F. Kennedy Presidential Library and Museum
Image for University of Massachusetts Boston

University of Massachusetts Boston

Enjoy the collegiate vibe when you visit University of Massachusetts Boston, during your trip to Boston. Experience the fascinating museums or attend a sporting event in this walkable area.

University of Massachusetts Boston
Image for Edward Kennedy Institute for the US Senate

Edward Kennedy Institute for the US Senate

Explore the campus of Edward Kennedy Institute for the US Senate, during your travels in Boston. Stroll along the waterfront or attend a sporting event in this vibrant area.

Edward Kennedy Institute for the US Senate

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $107
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

CA $239
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
Image for Boston Freedom Trail Daily Walking Tour

Boston Freedom Trail Daily Walking Tour

CA $35
Per adult
90% of travellers recommend
Boston Freedom Trail Daily Walking Tour
See all activities in Boston

Other vacations you might like

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