Chestnut Hill Trip

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Price found within the past 48 hours. Click for updated prices.
  • Lobby sitting area
    Jun 22 - Jun 27

    The Atlas Hotel + Flight

    Allston
    5 nights
    4.5 star property
    9.4/10 - Exceptional (108 reviews)
    "The property is objectively beautiful. Well designed and tidy. Our room was large and comfortable. Unfortunately our room had issues with hot water - couldn’t take a shower for longer than 8 mins or so without it going cold. Happened three different times at three different times of the day. Housekeeping also entirely skipped our room one day which was a bit of a disappointment after coming back from a long day of walking and looking forward to crawling into a comfy, clean bed. Hotel staff..."
    Reviewed May 20, 2026
    Return • Tucson (TUS) - Boston (BOS)
    TUS - BOS • 1 stop BOS - TUS • 1 stop
    ₹184,099
    ₹133,591
    per traveller
    found 15 hours ago
    The Atlas Hotel
  • Standard Room, 1 Queen Bed | Premium bedding, in-room safe, iron/ironing board, free WiFi
    Jun 22 - Jun 27

    Hotel Ivy Boston Common + Flight

    Bay Village
    5 nights
    2.5 star property
    8.4/10 - Very good (1,453 reviews)
    "Clean rooms, staff friendly"
    Reviewed May 21, 2026
    Return • Tucson (TUS) - Boston (BOS)
    TUS - BOS • 1 stop BOS - TUS • 1 stop
    Save 100% on your flight
    ₹281,369
    ₹157,337
    per traveller
    found 15 hours ago
    Hotel Ivy Boston Common
  • Miscellaneous
    Jun 22 - Jun 27

    Raffles Boston + Flight

    Back Bay
    5 nights
    5.0 star property
    9.6/10 - Exceptional (264 reviews)
    "didn't meet expectation"
    Reviewed May 18, 2026
    Return • Tucson (TUS) - Boston (BOS)
    TUS - BOS • 1 stop BOS - TUS • 1 stop
    Save 100% on your flight
    ₹436,308
    ₹297,086
    per traveller
    found 15 hours ago
    Raffles Boston
  • Front of property
    Jun 22 - Jun 27

    Eurostars The Boxer + Flight

    West End
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,489 reviews)
    "I liked the location. The room itself was small and it had a dank smell. Otherwise everything was fine. Nice lobby and restaurant on site."
    Reviewed May 21, 2026
    Return • Tucson (TUS) - Boston (BOS)
    TUS - BOS • 1 stop BOS - TUS • 1 stop
    Save 100% on your flight
    ₹201,773
    ₹142,009
    per traveller
    found 15 hours ago
    Eurostars The Boxer
  • 3 restaurants; breakfast, lunch, dinner, and brunch served
    Jun 22 - Jun 27

    The Charles Hotel + Flight

    West Cambridge
    5 nights
    4.0 star property
    9.4/10 - Exceptional (1,003 reviews)
    "I remain impressed with the Charles Hotel. The rooms are very comfortable. The location perfect when doing things around Harvard Square. The restaurant and bars are great and the the staff very helpful. Well worth the price."
    Reviewed May 21, 2026
    Return • Tucson (TUS) - Boston (BOS)
    TUS - BOS • 1 stop BOS - TUS • 1 stop
    Save 100% on your flight
    ₹237,364
    ₹170,551
    per traveller
    found 15 hours ago
    The Charles Hotel

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

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 ₹22,268 per night from 25 May to 26 May
₹22,268
₹29,212 total
25 May - 26 May
includes taxes & fees
9.6/10 Exceptional! (4,352 reviews)
"A truly excellent experience at the Seaport Hotel. All of the staff I encountered were friendly and helpful. My room was very nicely appointed with thoughtful extras. The details seem to matter here and you can’t beat the location. Don’t miss the PopUp Bagel shop 1 block away."

Reviewed on 21 May 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is ₹12,193 per night from 25 May to 26 May
₹12,193
₹14,199 total
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (2,626 reviews)
"I was unsure and apprehensive about staying in a hotel with a shared restroom facility. The Revolution was exceptionally clean and the facilities were private. A surprisingly positive experience!"

Reviewed on 22 May 2026

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 ₹17,239 per night from 29 May to 30 May
₹17,239
₹23,996 total
29 May - 30 May
includes taxes & fees
9.2/10 Wonderful! (4,649 reviews)
"Breakfast was nice its alacarte , pool very poor and no service on the pool , spa slots are very limited and they are off every Tuesday and Wednesday"

Reviewed on 19 May 2026

Omni Boston Hotel at the Seaport
See all 3,937 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_BostonCollege_6092291_05

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 fascinating museums 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.