Title: Chestnut Hill Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $856 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.

![Studio Allston Hotel](https://images.trvl-media.com/lodging/23000000/22760000/22757100/22757092/a522d616_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Studio Allston Hotel

Brighton

CA $856

per person

Mar 18 - Mar 24

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

8.6/10 Excellent! (1,175 reviews)

Staff was friendly. Room was clean

Reviewed on Feb 5, 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 $1,711

per person

Mar 18 - Mar 24

found 1 hour 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

![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 $1,490

per person

Apr 3 - Apr 6

found 1 day 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

![Maverick Suites at 245 Newbury St](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/2e7614de_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Maverick Suites at 245 Newbury St

Back Bay

CA $1,069

per person

Mar 18 - Mar 24

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

8.2/10 Very Good! (151 reviews)

Room was clean and a good size. Location was perfect - walking distance to where I needed to be.

Reviewed on Dec 2, 2025

## 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

![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 $137

CA $216 total

Feb 22 - Feb 23

includes taxes & fees

8.2/10 Very Good! (3,113 reviews)

The hotel itself is beautiful. The lobby is grand with a vibrant bar, restaurant in the center. The staff is friendly. This was a weekend away for me and my 10 year old daughter and we wanted something luxurious. Since it was so cold outside I knew we were going to be in the room a lot. I know the ...

Reviewed on Feb 6, 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

Feb 8 - Feb 9

includes taxes & fees

9.2/10 Wonderful! (6,199 reviews)

Best price for the location! Always clean and great staff!

Reviewed on Feb 4, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=202814&PinnedHotelID=202814&HadPinnedHotel=true&regionId=89077)

![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

CA $88

CA $103 total

Feb 9 - Feb 10

includes taxes & fees

9/10 Wonderful! (2,439 reviews)

Excellent customer service, beautiful room!!

Reviewed on Jan 31, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=30080227&PinnedHotelID=30080227&HadPinnedHotel=true&regionId=89077)

[See all 4,006 properties in Chestnut Hill](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%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

4/5(15 reviews)

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

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)

![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

4.5/5(27 reviews)

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

[](https://expedia.ca/Gillette-Stadium-Boston.d6034500.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 $73

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 $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)

[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.