Title: Dorchester Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,314 Expedia.ca

[Dorchester Travel Guide](https://expedia.ca/Boston-Dorchester.dx97469)[Hotels in Dorchester](https://expedia.ca/Dorchester-Boston-Hotels.0-n97469-0.Travel-Guide-Filter-Hotels)[Flights to Boston](https://expedia.ca/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights)[Things to do in Boston](https://expedia.ca/Things-To-Do-In-Boston.d178239.Travel-Guide-Activities)[Dorchester Car Rentals](https://expedia.ca/Car-Rentals-In-Dorchester.d97469.Car-Rental-Guide)

![](https://images.trvl-media.com/place/97469/339e3d2b-3377-4ef8-8d22-77ab1c757985.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Dorchester Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

## Top Holiday Package Deals in Dorchester

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

![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/ee935931_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars The Boxer

West End

CA $1,314

per person

May 26 - May 30

found 3 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) to Boston (BOS)

8.6/10 Excellent! (1,395 reviews)

AC was perfect. Room was clean and picture perfect. Amenities were wonderful and plentiful. All of the staff were pleasant, helpful and a general joy to interact with. Walkability and closeness to TD garden, Quincy Market, shopping and restaurants was amazing. Hotel has a beautiful bar and restaurant attached and the ability to do luggage consignment made it a no brainer. A place like this makes traveling and dealing with odd departure and arrival times of flights less stressful. One downside was that the ambient lighting in the hallways was a little dark for people not used to such low levels. The only other, was that the cabinet holding the mini fridge was very fragile and the door felt like it might fall off if touched wrong. Probably only an issue for that particular room, but younger children would have probably pulled the door off just by opening it. Otherwise, this was an amazing hotel and an amazing stay. Will be back to stay here the next time we travel to Boston to see games.

Reviewed on Mar 19, 2026

![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Boston Harbor Hotel

North End

CA $1,865

per person

May 2 - May 5

found 22 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) to Boston (BOS)

9.8/10 Exceptional! (1,001 reviews)

Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return!

Reviewed on Mar 14, 2026

![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/54f3deb7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Langham, Boston

Downtown Boston

CA $1,451

per person

May 2 - May 5

found 22 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) to Boston (BOS)

9.6/10 Exceptional! (1,004 reviews)

Great location within walking distance to many of Boston’s best spots including Faneuil Market, North End “little Italy,” and more! The hotel staff were welcoming and kind during our visit, and our room was well kept. No complaints.

Reviewed on Mar 14, 2026

![The Inn at Hastings Park, Relais & Chateaux - Boston](https://images.trvl-media.com/lodging/8000000/7990000/7980700/7980601/8dcd0e80_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Inn at Hastings Park, Relais & Chateaux - Boston

CA $1,561

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.6/10 Exceptional! (252 reviews)

Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

![The Boston Hotel](https://images.trvl-media.com/lodging/101000000/100140000/100136300/100136229/54a79fec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Boston Hotel

Brighton

CA $1,556

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

7.4/10 Good! (853 reviews)

Very nice and clean staff was very polite

Reviewed on Mar 17, 2026

## Where to stay in Dorchester

Find the best Dorchester areas and neighborhoods for the activities you enjoy most. [Learn more about Dorchester](https://expedia.ca/Boston-Dorchester.dx97469)

![Downtown Boston showing a city and night scenes as well as a small group of people](https://images.trvl-media.com/place/6340396/147aba27-8694-4725-895d-0beb6077ab67.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Boston&DestID=6340396&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Back Bay featuring a city, heritage architecture and street scenes](https://images.trvl-media.com/place/800016/ecea0c09-2ade-4d56-b74d-09ed645f6ef5.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Back Bay

1 out of top 10 points of interest in this area

4.5/5(272 area reviews)

 Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower. 

[Find hotel + flight trips in Back Bay](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Back%20Bay&DestID=800016&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Seaport District featuring a high-rise building, a river or creek and a city](https://images.trvl-media.com/place/6146535/5487f5d9-6748-43ca-b7bd-e50e2e9d2a27.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Seaport District

4.5/5(64 area reviews)

 Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge. 

[Find hotel + flight trips in Seaport District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Seaport%20District&DestID=6146535&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![East Boston showing sailing, a city and a river or creek](https://images.trvl-media.com/place/99089/ffb9946d-6df5-4058-a132-e180995361ac.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### East Boston

4/5(28 area reviews)

 First a shipbuilding hub and now home of Logan Airport, Boston’s easternmost neighborhood is a multicultural area with great ethnic restaurants and historic sites. 

[Find hotel + flight trips in East Boston](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Boston&DestID=99089&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Beacon Hill which includes landscape views](https://images.trvl-media.com/place/77649/9741c4ac-c840-46d1-b907-3b388935c98f.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Beacon Hill

1 out of top 10 points of interest in this area

5/5(1 area review)

 Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations. 

[Find hotel + flight trips in Beacon Hill](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Beacon%20Hill&DestID=77649&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Dorchester Hotel Deals

![Ramada by Wyndham Boston](https://images.trvl-media.com/lodging/1000000/10000/300/293/0b01c717_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Ramada by Wyndham Boston

800 Morrissey Blvd Boston MA

Fully refundableReserve now, pay when you stay

CA $120

CA $139 total

Mar 29 - Mar 30

includes taxes & fees

6.8/10 (1,654 reviews)

I had a good stay the staff were friendly and the room was clean i would definitely recommend this hotel

Reviewed on Mar 21, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=293&PinnedHotelID=293&HadPinnedHotel=true&regionId=97469)

![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/d1e2c1a3_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Fully refundableReserve now, pay when you stay

CA $186

CA $272 total

Apr 5 - Apr 6

includes taxes & fees

9.2/10 Wonderful! (4,521 reviews)

Clean room, great location and staff

Reviewed on Mar 20, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=68014393&PinnedHotelID=68014393&HadPinnedHotel=true&regionId=97469)

![Hilton Boston Park Plaza](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Boston Park Plaza

50 Park Plaza Boston MA

Fully refundableReserve now, pay when you stay

CA $201

CA $290 total

Apr 5 - Apr 6

includes taxes & fees

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=4215&PinnedHotelID=4215&HadPinnedHotel=true&regionId=97469)

[See all 4,306 properties in Dorchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&regionId=97469)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Dorchester vacation package cost?

### How do I get a cheap travel package to Dorchester?

### Where should I stay in Dorchester?

### What are the top hotels in Dorchester?

### How far in advance should I book my Dorchester vacation?

### What does an Expedia Dorchester travel package include?

### What should I know before booking a Dorchester travel package?

### Can I choose my airline with a Dorchester Expedia vacation package?

### If I'm not able to travel, can I cancel my Dorchester vacation package?

### Discover the most popular places to visit in Dorchester

![John F. Kennedy Presidential Library and Museum which includes modern architecture and interior views](https://images.trvl-media.com/place/6070087/d2886c19-a0ee-42f0-b4a9-730253a26186.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.ca/John-F-Kennedy-Presidential-Library-And-Museum-Dorchester.d6070087.Vacation-Attraction)

### Things to do

![Boston Hop-On Hop-Off Trolley Tour](https://mediaim.expedia.com/localexpert/172982/6f42f390-62da-409c-a976-5a931abb154f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

CA $72

per adult

**90%** of travellers recommend

[](https://expedia.ca/things-to-do/boston-old-town-trolley-hop-on-hop-off-city-tour.a172982.activity-details)

![Boston CityPASS: Admission to Top 4 Boston Attractions](https://mediaim.expedia.com/localexpert/173116/5d73576c-38be-4337-8351-c85e937f9492.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Boston CityPASS®: Admission to Top 4 Attractions

CA $108

per adult

**92%** of travellers recommend

[](https://expedia.ca/things-to-do/boston-citypass-admission-to-top-4-attractions.a173116.activity-details)

![Zac tells a story about the John Harvard statue](https://mediaim.expedia.com/localexpert/1349360/d8650b03-f74e-4c81-8957-837ce0090701.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Harvard University Campus Guided Walking Tour

CA $32

per adult

**92%** of travellers recommend

[](https://expedia.ca/things-to-do/harvard-university-campus-guided-walking-tour.a1349360.activity-details)

[See all activities in Boston](https://expedia.ca/things-to-do/search?rid=97469)

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

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