Title: Chestnut Hill Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,032 Expedia.ca

[Chestnut Hill Travel Guide](https://expedia.ca/Boston-Chestnut-Hill.dx89077)[Hotels in Chestnut Hill](https://expedia.ca/Chestnut-Hill-Boston-Hotels.0-n89077-0.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)[Chestnut Hill Car Rentals](https://expedia.ca/Car-Rentals-In-Chestnut-Hill.d89077.Car-Rental-Guide)

![](https://images.trvl-media.com/place/7091/40d2101a-9cd1-49a2-a1d2-7cf070ea397a.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Chestnut Hill Vacation Packages

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

Photo by Ed Gaffny

- ##  
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 Chestnut Hill Vacation

With plenty of highlights as well as hidden gems, this city is best experienced with a Chestnut Hill vacation package. Find somewhere to stay in Downtown Boston, which is great for nightlife, shopping and bars and pubs. Fill your schedule with visits to [Boston College](https://www.expedia.ca/Boston-College-Commonwealth.d6092291.Vacation-Attraction), [Paradise Rock Club](https://www.expedia.ca/Paradise-Rock-Club-Allston.d553248621533127008.Vacation-Attraction) and [Agganis Arena](https://www.expedia.ca/Agganis-Arena-Allston.d6229782.Vacation-Attraction), some of the attractions you simply have to see during your trip to Chestnut Hill. Browse Expedia's wide range of travel options and start organizing your perfect vacation to Chestnut Hill today.

## Top Holiday Package Deals in Chestnut Hill

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

![Global Luxury Suites East Boston](https://images.trvl-media.com/lodging/60000000/59300000/59296500/59296491/a5dc30b0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Global Luxury Suites East Boston

East Boston

CA $1,032

per person

Apr 24 - Apr 28

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Boston (BOS)

6.8/10 (173 reviews)

The room is clean and the furniture is pretty, but since it's part of an apartment complex, you don't have immediate help with extra sheets or heater support; so first two days out 4, we had to deal with the cold of the room. Third and 4th, since we had called for help, they did left the extra sheets and fixed the thermostat.

Reviewed on Dec 6, 2025

![Mandarin Oriental, Boston](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/be69f75d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Mandarin Oriental, Boston

Back Bay

CA $1,575

per person

Feb 27 - Mar 2

found 18 hours ago

Roundtrip flight included

Toronto (YTZ) to Boston (BOS)

9.4/10 Exceptional! (376 reviews)

Immaculate, convenient, good food, great staff, perfect facilities, and nice little touches.

Reviewed on Nov 21, 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 $1,977

per person

Apr 9 - Apr 12

found 5 hours ago

Roundtrip non-stop flight included

Calgary (YYC) 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

![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/0f66f064_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Raffles Boston

Back Bay

CA $2,680

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (181 reviews)

Attentive Staff, gorgeous property, clean rooms

Reviewed on Jan 25, 2026

![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/db81308e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars The Boxer

West End

CA $1,261

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

8.6/10 Excellent! (1,337 reviews)

I didn’t like that I was surprised with “hospitality fee” for almost $70 upon arrival. Had I known that I would’ve stayed somewhere else. That’s why I paid in advance on Expedia.

Reviewed on Jan 23, 2026

## Where to stay in Chestnut Hill

Find the best Chestnut Hill areas and neighborhoods for the activities you enjoy most. [Learn more about Chestnut Hill](https://expedia.ca/Boston-Chestnut-Hill.dx89077)

![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

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)

![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)

## Chestnut Hill 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 $176

CA $252 total

Feb 1 - Feb 2

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=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=79888&PinnedHotelID=79888&HadPinnedHotel=true&regionId=89077)

![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 $133

CA $210 total

Feb 22 - Feb 23

includes taxes & fees

8.2/10 Very Good! (3,122 reviews)

The room was clean, nice, and the lobby was decorated super pretty for Christmas. We just hoped for streaming on the TV in the room

Reviewed on Jan 26, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=4215&PinnedHotelID=4215&HadPinnedHotel=true&regionId=89077)

![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 29 - Jan 30

includes taxes & fees

9.2/10 Wonderful! (6,199 reviews)

Great staff, easy check in

Reviewed on Jan 27, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F01%2F2026&endDate=30%2F01%2F2026&selected=202814&PinnedHotelID=202814&HadPinnedHotel=true&regionId=89077)

[See all 3,988 properties in Chestnut Hill](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=29%2F01%2F2026&endDate=30%2F01%2F2026&regionId=89077)

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 Chestnut Hill vacation package cost?

### What are the cheapest months to go to Chestnut Hill?

### How many days is enough for Chestnut Hill?

### How to find the best Chestnut Hill package deals?

### Is it cheaper to book a Chestnut Hill vacation as a package?

### When to book a vacation package to Chestnut Hill?

### How to plan a trip to Chestnut Hill?

> 1. Choose when to travel: Check your diary and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to escape to Chestnut Hill.
> 2. Set your budget: Factor in expenses such as flights, meals and transportation when working out how much to save for your trip to Chestnut Hill. Then, select a hotel that suits your budget, whether that's a wallet-friendly stay or a deluxe retreat.
> 3. Decide your trip length: Think about how much time you want to spend exploring Chestnut Hill. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
> 4. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, book the right Chestnut Hill vacation package for you.

### Discover the most popular places to visit in Chestnut Hill

![Boston_BostonCollege_6092291_05](https://images.trvl-media.com/place/6092291/d3fbc729-8f9a-4a76-9ed2-58c8f6aeade9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Boston College

Take a campus tour or just explore the area of Boston College, during your trip to Boston. Stroll along the riverfront or attend a sporting event in this vibrant area. 

[](https://expedia.ca/Boston-College-Chestnut-Hill.d6092291.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

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)

![Gillette Stadium is also home to the New England Revolution, our pro soccer team.  Tickets are easy to get and not crazy expensive.  And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!](https://images.trvl-media.com/place/8136/b9d0e965-3860-4aa0-bd75-1fe651b315dc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theater scene and great live music. 

[](https://expedia.ca/Gillette-Stadium-Boston.d6034500.Vacation-Attraction)

### Things to do

![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 $110

per adult

**92%** of travellers recommend

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

![Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must must-visit. ](https://mediaim.expedia.com/localexpert/46312679/f4dc7e7e-3f89-44f1-8c94-790c64c45eec.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### View Boston Observation Deck Admission Tickets

CA $47

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/view-boston-observation-deck-admission-tickets.a46312679.activity-details)

![Go City: Boston All-Inclusive Pass with 45+ Attractions](https://mediaim.expedia.com/localexpert/173074/064eb1cc-eb4f-4535-bc3f-dbc4e50db8ab.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Go City: Boston All-Inclusive Pass with 45+ Attractions

CA $117

per adult

**80%** of travellers recommend

[](https://expedia.ca/things-to-do/go-city-boston-all-inclusive-pass-with-45-attractions.a173074.activity-details)

[See all activities in Boston](https://expedia.ca/things-to-do/search?rid=89077)

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