Title: Dorchester Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $729 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.

![Lakeside Inn](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/28347172_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Lakeside Inn

CA $729

per person

May 22 - May 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

7.6/10 Good! (2,331 reviews)

Well if you like jamming out to Enter Sandman at 11:30 at night, this is the place for you! Live band, small rooms, and paper thin walls do not mix well for travelers who are there to sleep and not party. This is not a terrible place but we were looking for sleep as we had early morning flights.

Reviewed on Mar 15, 2026

![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 $1,255

per person

May 22 - May 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

8.6/10 Excellent! (1,395 reviews)

The king "deluxe" room was a weird irregular shape . The bed was on an angle and there was a tall shelf like desk area that was ackward to pass each time getting up for the bathroom . No microwave and outdated furniture. However the room was clean, bed was comfortable and the staff were really great . Also a good location many things were walking distance away .

Reviewed on Mar 16, 2026

![The Colonnade Hotel Back Bay](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/54848539_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Colonnade Hotel Back Bay

Back Bay

CA $1,170

per person

May 22 - May 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.2/10 Wonderful! (2,282 reviews)

Great stay! All around very happy!

Reviewed on Mar 15, 2026

![AutoCamp Cape Cod](https://images.trvl-media.com/lodging/50000000/49180000/49175900/49175859/da4b66b1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### AutoCamp Cape Cod

CA $1,035

per person

May 28 - Jun 3

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (306 reviews)

We had a wonderful stay here on Valentine’s Day weekend. It was the first time we stayed at a camp ground and definitely the first time staying in an AirStream. The clubhouse was sooo nice! Staff were great. Good menu options and merch as well. Picked up an AutoCamp beanie! Live music was awesome. My only complaint is we had no hot water! That was tough being that we are in the middle of the winter and it was already freezing outside. Hot showers would have been nice! Other than that we’re planning for a summer weekend here

Reviewed on Feb 17, 2026

![enVision Hotel Boston Everett](https://images.trvl-media.com/lodging/18000000/17520000/17515300/17515205/db40fbb7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### enVision Hotel Boston Everett

CA $1,130

per person

May 22 - May 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

8.6/10 Excellent! (1,006 reviews)

My go to whenever in Boston

Reviewed on Mar 13, 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(271 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)

![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)

![Boston Harbor which includes performance art, music and a bay or harbor](https://images.trvl-media.com/place/553248634340925170/190102c5-6ec7-4f3d-9631-9a7f002e9676.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### North End

1 out of top 10 points of interest in this area

4.5/5(18 area reviews)

 Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries. 

[Find hotel + flight trips in North End](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=North%20End&DestID=6146485&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 (1,650 reviews)

room reaked of cigarettes, bed was stained with makeup and who knows what else, was so dirty and gross that we left and never even stayed one out of our 2 nights that we paid for

Reviewed on Mar 16, 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 $209

CA $299 total

Mar 22 - Mar 23

includes taxes & fees

9.2/10 Wonderful! (4,520 reviews)

Clean room, convenient and very friendly staff

Reviewed on Mar 16, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%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 $196

CA $284 total

Mar 22 - Mar 23

includes taxes & fees

8.4/10 Very Good! (3,125 reviews)

Rooms were clean, custodial staff were very friendly, room was over priced considering it was somewhat outdated furnishings, amenities were lacking as well. Valet parking was outrageous at $70/day and the alternative was $42 with no in/out privileges.

Reviewed on Mar 16, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=4215&PinnedHotelID=4215&HadPinnedHotel=true&regionId=97469)

[See all 4,314 properties in Dorchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F03%2F2026&endDate=18%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

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 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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