Title: Eastern Massachusetts Vacation Packages & Trips 2026 from CA $1,276 | Expedia.ca

[Eastern Massachusetts Travel Guide](https://expedia.ca/Eastern-Massachusetts.dx6234158)[Hotels in Eastern Massachusetts](https://expedia.ca/Eastern-Massachusetts-Hotels.d6234158.Travel-Guide-Hotels)[Vacation Rentals in Eastern Massachusetts](https://expedia.ca/Eastern-Massachusetts-Vacation-Rentals.d6234158.Travel-Guide-VacationRentals)[Flights to Eastern Massachusetts](https://expedia.ca/Cheap-Flights-To-Eastern-Massachusetts.d6234158.Travel-Guide-Flights)[Things to do in Eastern Massachusetts](https://expedia.ca/Things-To-Do-In-Eastern-Massachusetts.d6234158.Travel-Guide-Activities)[Eastern Massachusetts Car Rentals](https://expedia.ca/Car-Rentals-In-Eastern-Massachusetts.d6234158.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6228823/aff3ef32-252a-4bea-af5d-32b409f84451.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Eastern Massachusetts Vacation Packages

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

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

### Your Eastern Massachusetts Vacation

Choose one of our vacation packages to Eastern Massachusetts and wander wherever your inner adventurer desires. Dining and culture are just a couple of the things you can look forward to in this exciting destination. Your trip to Eastern Massachusetts wouldn't be complete without experiencing some of its most well-known cities, starting with [Boston](https://www.expedia.ca/Boston.d178239.Destination-Travel-Guides). Two of the top attractions here include Fenway Park and TD Garden. [Hyannis](https://www.expedia.ca/Hyannis.d1544.Destination-Travel-Guides) is another favourite city with Eastern Massachusetts travellers. Visitors to this exciting destination enjoy Cape Codder Water Park and Cape Cod Inflatable Park. From the instant you book your Eastern Massachusetts vacation to when you get back home, Expedia will be with you each step of the way.

## Top Eastern Massachusetts Vacation Deals

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

![Hilton Boston Back Bay](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Boston Back Bay

Fenway–Kenmore

CA $1,276

per person

Mar 22 - Mar 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

8.6/10 Excellent! (1,229 reviews)

Room is amazing I love how room service even fold our pajama. Impeccable into details. They sent a microwave to our room as per request. I hope they have Hot Water ready in lobby 24/7\. Access to that is very limited

Reviewed on Jan 20, 2026

![The Whitney Hotel](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/59f2dc0e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Whitney Hotel

Beacon Hill

CA $1,724

per person

Mar 22 - Mar 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (482 reviews)

Our second stay there, love it

Reviewed on Dec 25, 2025

![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 $3,101

per person

Mar 22 - Mar 28

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.8/10 Exceptional! (1,005 reviews)

Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/66098bc6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Charles Hotel

West Cambridge

CA $1,931

per person

Mar 22 - Mar 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (1,003 reviews)

Room very well appointed and gym was the stand out

Reviewed on Jan 25, 2026

![The Newbury Boston](https://images.trvl-media.com/lodging/1000000/10000/400/395/de8ba46e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Newbury Boston

Back Bay

CA $2,922

per person

Mar 29 - Apr 5

found 9 hours ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Boston (BOS)

9.4/10 Exceptional! (536 reviews)

Staff was friendly and flexible ! Rooms were spacious and beautiful, the housekeeping was not as clean or organized or detailed as other places I’ve been to but still good

Reviewed on Jan 4, 2026

## Where to stay in Eastern Massachusetts

Find the best Eastern Massachusetts areas and neighborhoods for the activities you enjoy most. [Learn more about Eastern Massachusetts](https://expedia.ca/Eastern-Massachusetts.dx6234158)

![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)

![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

1 out of top 10 points of interest in this area

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)

![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)

![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)

## Ready to book your vacation to Eastern Massachusetts?

Choose your dates

## Eastern Massachusetts Hotel Deals

![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Seaport Hotel Boston

1 Seaport Lane Boston MA

Fully refundableReserve now, pay when you stay

CA $198

CA $277 total

Jan 31 - Feb 1

includes taxes & fees

9.6/10 Exceptional! (3,935 reviews)

Room was spotless. Staff was accommodating and friendly. Only complaint is towels were too rough and stiff. Need a little bit softener. Otherwise, happy with my stay and will book there again in the future.

Reviewed on Jan 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=31%2F01%2F2026&endDate=01%2F02%2F2026&selected=79888&PinnedHotelID=79888&HadPinnedHotel=true&regionId=6234158)

![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 $122

CA $198 total

Feb 22 - Feb 23

includes taxes & fees

8.2/10 Very Good! (3,109 reviews)

Clean and amenities were great

Reviewed on Jan 21, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=4215&PinnedHotelID=4215&HadPinnedHotel=true&regionId=6234158)

![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Harborside Inn Of Boston

185 State St Boston MA

CA $147

CA $171 total

Jan 27 - Jan 28

includes taxes & fees

9.2/10 Wonderful! (6,171 reviews)

Everything was perfect. Loved the cabin room. My husband who never sleeps slept until 10 am

Reviewed on Jan 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=27%2F01%2F2026&endDate=28%2F01%2F2026&selected=202814&PinnedHotelID=202814&HadPinnedHotel=true&regionId=6234158)

[See all 15,851 properties in Eastern Massachusetts](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F01%2F2026&endDate=28%2F01%2F2026&regionId=6234158)

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)

### Discover the most popular places to visit in Eastern Massachusetts

![Boston Common which includes flowers, a garden and landscape views](https://images.trvl-media.com/place/507377/07fb4e8e-e473-4766-bc75-7dd4f742d04f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Boston Common

4.5/5(518 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

[](https://expedia.ca/Boston-Common-Beacon-Hill.d507377.Vacation-Attraction)

![Fenway Park featuring a sporting event and night scenes as well as a large group of people](https://images.trvl-media.com/place/6023384/56814c91-ad37-4ef6-9e12-186349c04e42.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Fenway Park

4.5/5(305 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

[](https://expedia.ca/Fenway-Park-FenwayKenmore.d6023384.Vacation-Attraction)

![Boston's Zakim Bridge](https://images.trvl-media.com/place/6070137/28b26e99-a684-4d32-8b62-4180d99b863d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### TD Garden

4.5/5(240 reviews)

Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area. 

[](https://expedia.ca/TD-Garden-West-End.d6070137.Vacation-Attraction)

### What to do in Eastern Massachusetts

![Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour](https://mediaim.expedia.com/localexpert/823381/04e76f58-c1d8-4768-84d0-bcae3ea6e07f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Cape Ann Harbor: Self-Guided Driving Audio Tour

CA $24

per traveller

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/cape-ann-harbor-self-guided-driving-audio-tour.a823381.activity-details)

![Cape Ann Self-Guided Driving Tour in Gloucester and Rockport](https://mediaim.expedia.com/localexpert/3060314/25d71e0c-f1f2-40ad-9b58-41d96a7c86e7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

CA $24

per traveller

**80%** of travellers recommend

[](https://expedia.ca/things-to-do/cape-ann-self-guided-driving-tour-in-gloucester-and-rockport.a3060314.activity-details)

![Massachusetts Highlights: Freedom Trail, Salem & More Tour](https://mediaim.expedia.com/localexpert/5247794/991bb3ab-4de4-47da-8b84-5a4e09a0b2d6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

CA $69

per adult

[](https://expedia.ca/things-to-do/massachusetts-self-guided-audio-tour-bundle-10-tours.a5247794.activity-details)

[See all activities in Eastern Massachusetts](https://expedia.ca/things-to-do/search?rid=6234158)

## Frequently asked questions

### Can I cancel my flight booking to Eastern Massachusetts due to COVID-19?

### What's the best way to find cheap flights to Eastern Massachusetts that have flexible change policies?

### What are some of the general tips for travelers to Eastern Massachusetts during the COVID-19 outbreak?

> - Find out if any travel restrictions apply to your origin and destination before booking your flight. Also check if there are any special conditions you'll need to follow on arrival, such as mandatory quarantining.
> - Keep your face mask on during airport screening. A TSA employee will require you to temporarily lower your mask for ID purposes.
> - Rather than handing a TSA employee your boarding pass, position it straight on the scanner yourself. When that's done, hold it up for inspection.
> - You can take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. This will need to be taken out for X-ray screening.
> - Remove items from your pockets, such as your wallet and phone, and place them in your carry-on instead of the bins. This will reduce handling during the screening process.
> - If you're taking food on board, put it in a clear plastic bag and then into a scanning bin. This lessens the likelihood that a TSA employee will need to handle your carry-on bag or food container for closer inspection.

### Which airlines fly to Eastern Massachusetts?

### How can I find cheap tickets to Eastern Massachusetts?

### How much is a flight to Eastern Massachusetts?

### What are the most popular airports to fly into in Eastern Massachusetts?

### When is the cheapest time to fly to Eastern Massachusetts?

### How much is a plane ticket to Eastern Massachusetts?

### Which airlines with flights to Eastern Massachusetts employ COVID-19 cleanliness policies?

> - JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
> - Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
> - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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- [Catamount Ski Area ](https://www.expedia.ca/Catamount-Ski-Area-United-States-of-America.d6087211.Vacation-Attraction)
- [Merrimack Valley Vacations ](https://www.expedia.ca/Merrimack-Valley.d6047671.Destination-Travel-Guides)
- [Visit Merrimack Valley ](https://www.expedia.ca/Merrimack-Valley.dx6047671)
- [New England Vacations ](https://www.expedia.ca/New-England.d553248635975748760.Destination-Travel-Guides)
- [Visit New England ](https://www.expedia.ca/New-England.dx553248635975748760)
- [Southeast Massachusetts Vacations ](https://www.expedia.ca/Southeast-Massachusetts.d6047675.Destination-Travel-Guides)
- [Visit Southeast Massachusetts ](https://www.expedia.ca/Southeast-Massachusetts.dx6047675)

- [Car rentals near New England ](https://www.expedia.ca/Car-Rentals-In-New-England.d553248635975748760.Car-Rental-Guide)

- [Southeast Massachusetts Vacation Rentals ](https://www.expedia.ca/Southeast-Massachusetts-Vacation-Rentals.d6047675.Travel-Guide-VacationRentals)

- [Things to do in Merrimack Valley ](https://www.expedia.ca/Things-To-Do-In-Merrimack-Valley.d6047671.Travel-Guide-Activities)
- [Things to do in New England ](https://www.expedia.ca/Things-To-Do-In-New-England.d553248635975748760.Travel-Guide-Activities)
- [Things to do in Southeast Massachusetts ](https://www.expedia.ca/Things-To-Do-In-Southeast-Massachusetts.d6047675.Travel-Guide-Activities)

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