Chestnut Hill Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Ed Gaffny

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
Downtown Boston which includes a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Harbor and Boston Massacre Site, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

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Top hotels in Chestnut Hill

The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Fully refundableReserve now, pay when you stay
The price is 3.837.087 ₫ per night from 24 Nov to 25 Nov
3.837.087 ₫
5.388.576 ₫ total
24 Nov - 25 Nov
includes taxes & fees
9.4/10 Exceptional! (6,706 reviews)
Everything was great! The only thing is that this site said room was over 300 sq ft and it was not. Then again- who stays in their room???

Reviewed on 14 Nov 2025

The Dagny Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (2,241 reviews)
I love this hotel. The rooms are immaculately clean, the staff is great, and the communal bathrooms are always spotless. If you are OK with not having a bathroom in your room, this is an ideal spot -- great neighborhood, awesome restaurant and bar on site, and a really fun/cool vibe. I've stayed ...

Reviewed on 14 Nov 2025

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The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is 4.321.400 ₫ per night from 26 Nov to 27 Nov
4.321.400 ₫
6.106.296 ₫ total
26 Nov - 27 Nov
includes taxes & fees
9/10 Wonderful! (4,198 reviews)
Spacious room that was spotless. Friendly and helpful staff. My favorite place to stay in Boston!

Reviewed on 14 Nov 2025

Omni Boston Hotel at the Seaport
See all 3,693 properties in Chestnut Hill
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.

Frequently asked questions

How much does a Chestnut Hill holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday to Chestnut Hill costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Chestnut Hill?
If you'd like to score a cheap Chestnut Hill holiday package, consider travelling in January, February and November. You'll usually find lower rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Chestnut Hill?
The ideal duration of your Chestnut Hill holiday depends on what you'd like to see and do. Typically, a few days to a week will give you plenty of time to hit all the leading attractions and discover some hidden spots along the way.
How to find the best Chestnut Hill package deals?
Start your search for a Chestnut Hill package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Chestnut Hill package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chestnut Hill getaway off to a flying start.
Is it cheaper to book a Chestnut Hill holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can tailor your Chestnut Hill trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Chestnut Hill?
If you have your Chestnut Hill holiday dates locked in, book early to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Chestnut Hill?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Chestnut Hill.
  2. Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodation will probably be the largest expense during your trip to Chestnut Hill.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Chestnut Hill. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Chestnut Hill holiday package that brings all your bookings together.

Popular places to visit

Boston College

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.

Boston College
Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

Harvard University