Chestnut Hill Trip

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Price found within the past 48 hours. Click for updated prices.
Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

2.5 out of 5
Price was ₹60,546, price is now ₹59,889 per person
₹59,889
per person
16 May - 18 May
found 1 day ago
Return direct flight included
Baltimore (BWI) to Boston (BOS)
7.8/10 Good! (154 reviews)
Minimal breakfast choices. Staff was helpful but place was a little run down. Was clean though and served its purose. Across from fair grounds and close to good restaurants.

Reviewed on 4 Apr 2026

Riverdale Inn

Riverdale Inn

2 out of 5
Price was ₹102,585, price is now ₹91,577 per person
₹91,577
per person
16 May - 18 May
found 1 day ago
Return direct flight included
Baltimore (BWI) to Boston (BOS)
6/10 (1,000 reviews)
everything was what I was looking for

Reviewed on 29 Jan 2026

MGM Springfield

MGM Springfield

4 out of 5
Metro Center
Price was ₹84,639, price is now ₹78,213 per person
₹78,213
per person
16 May - 18 May
found 1 day ago
Return direct flight included
Baltimore (BWI) to Boston (BOS)
9/10 Wonderful! (1,514 reviews)
Our room was clean, spacious, and very comfortable. The casino is well-maintained with a visible security presence that made us feel safe and relaxed. We had an outstanding dinner at Chandler Steakhouse; it’s a bit pricey, but absolutely worth it for the quality. On our last day, we also grabbed burgers at Wahlburgers—while the restaurant temperature was uncomfortably cold, the food was cooked to perfection and delicious! Thank you!

Reviewed on 3 Apr 2026

Hampton Inn & Suites Springfield/Downtown

Hampton Inn & Suites Springfield/Downtown

2.5 out of 5
South End
Price was ₹71,452, price is now ₹67,232 per person
₹67,232
per person
16 May - 18 May
found 1 day ago
Return direct flight included
Baltimore (BWI) to Boston (BOS)
8.6/10 Excellent! (1,002 reviews)
Very welcoming staff clean room efficient close to everything

Reviewed on 6 Apr 2026

Hilton Garden Inn-Springfield, MA

Hilton Garden Inn-Springfield, MA

3 out of 5
South End
Price was ₹67,045, price is now ₹66,096 per person
₹66,096
per person
16 May - 18 May
found 1 day ago
Return direct flight included
Baltimore (BWI) to Boston (BOS)
8.6/10 Excellent! (1,002 reviews)
Room is clean and recently updated. Staff was extremely helpful and kind. Parking is easy and free. Did not have breakfast or eat at the hotel.

Reviewed on 30 Mar 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
Downtown Boston

Downtown Boston

4.5/5(95 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Top hotels in Chestnut Hill

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 ₹17,421 per night from 11 Apr to 12 Apr
₹17,421
₹24,080 total
11 Apr - 12 Apr
includes taxes & fees
9.2/10 Wonderful! (4,564 reviews)
The property was nice

Reviewed on 6 Apr 2026

Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is ₹14,074 per night from 9 Apr to 10 Apr
₹14,074
₹19,564 total
9 Apr - 10 Apr
includes taxes & fees
9.6/10 Exceptional! (4,146 reviews)
Hotel has a beautiful view of the harbor and is well located - very easy to walk to dining and downtown. Room and hotel overall were clean and felt luxurious. Coach bed was comfortable as well. Loved having a door between the bedroom and living area! Overall great experience.

Reviewed on 6 Apr 2026

Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is ₹17,475 per night from 3 May to 4 May
₹17,475
₹24,142 total
3 May - 4 May
includes taxes & fees
8.4/10 Very Good! (3,138 reviews)
Room and bathroom were spotless. Great location to everything. There was a late night emergency evacuation and everything moved seamlessly (we were on the 15th floor and made it down in no time). Hotel restaurant and bar were very nice and was a great place for late night relaxing following a day ...

Reviewed on 6 Apr 2026

Hilton Boston Park Plaza
See all 3,966 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 from ₹59,889 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

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Boston College

4/5(5 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.

Boston College
McMullen Museum of Art is the university art museum of Boston College in Brighton, city of Boston, Massachusetts MA, USA.

McMullen Museum

You can study the exhibits at McMullen Museum, a museum with a storied past, during your trip to Newton. Experience the acclaimed art galleries or attend a sporting event in this vibrant area.

McMullen Museum
Fenway Park

Fenway Park

4.5/5(62 reviews)

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

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