Chestnut Hill Holidays

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Your Chestnut Hill Holiday

With plenty of highlights as well as hidden gems, this city is best experienced with a Chestnut Hill holiday 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, Paradise Rock Club and Agganis Arena, 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 organising your perfect holiday to Chestnut Hill today.

Price found within the past 48 hours. Click for updated prices.
  • Games room
    Aug 12 - Aug 17

    Meco Hotel - Hostel + Flight

    West End
    5 nights
    2.0 star property
    8.6/10 - Excellent (430 reviews)
    "Would definitely stay here again and again I loved it"
    Reviewed May 27, 2026
    Return • Edinburgh (EDI) - Boston (BOS)
    EDI - BOS • 1 stop BOS - EDI • 1 stop
    £1,807
    £1,236
    per traveller
    found 6 hours ago
    Meco Hotel - Hostel
  • Standard Room, 1 Queen Bed | Premium bedding, in-room safe, iron/ironing board, free WiFi
    Jul 10 - Jul 20

    Hotel Ivy Boston Common + Flight

    Bay Village
    10 nights
    2.5 star property
    8.4/10 - Very good (1,466 reviews)
    "Very helpful and accommodating staff, free luggage storage is very convenient, hotel is located centrally among lots of restaurants/bars and just minutes walking to China Town. The room was exactly what we needed. Would definitely stay again!"
    Reviewed May 27, 2026
    Return • Glasgow (GLA) - Boston (BOS)
    GLA - BOS • 1 stop BOS - GLA • 1 stop
    Save 100% on your flight
    £2,689
    £1,593
    per traveller
    found 11 hours ago
    Hotel Ivy Boston Common
  • Lobby sitting area
    Jul 10 - Jul 20

    The Atlas Hotel + Flight

    Allston
    10 nights
    4.5 star property
    9.4/10 - Exceptional (119 reviews)
    "The rooftop bar I could hear it until it closed at 1am was my only complaint"
    Reviewed May 27, 2026
    Return • Glasgow (GLA) - Boston (BOS)
    GLA - BOS • 1 stop BOS - GLA • 1 stop
    Save 100% on your flight
    £2,260
    £1,568
    per traveller
    found 11 hours ago
    The Atlas Hotel
  • Breakfast, lunch and brunch served
    Jun 27 - Jun 30

    The Langham, Boston + Flight

    Downtown Boston
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "Gorgeous property, excellent restaurants and the staff was very attentive and very kind....we'll definitely be back the next time we visit Boston! We loved our stay!"
    Reviewed May 26, 2026
    Return • Edinburgh (EDI) - Boston (BOS)
    EDI - BOS • 1 stop BOS - EDI • 1 stop
    £1,953
    £1,361
    per traveller
    found 1 day ago
    The Langham, Boston
  • Restaurant
    Aug 17 - Aug 26

    The Newbury Boston + Flight

    Back Bay
    9 nights
    5.0 star property
    9.4/10 - Exceptional (645 reviews)
    "Classy hotel with breathtaking views of Public Park / Boston Common. The room and bed were comfortable, in-room dining wonderful. The rooftop and lobby restaurants of the hotel, however, were not on par with its elegance. The lobby bar is noisy and unpleasant upon entering the building. Not well thought-out placement."
    Reviewed May 25, 2026
    Return • London (LHR) - Boston (BOS)
    LHR - BOS • 1 stop BOS - LHR • 1 stop
    Save 100% on your flight
    £3,408
    £2,380
    per traveller
    found 1 day ago
    The Newbury Boston

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 £211 per night from 31 May to 1 Jun
£211
31 May - 1 Jun
includes taxes & fees
9.6/10 Exceptional! (4,382 reviews)
"Great place to stay!!"

Reviewed on 27 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 £137 per night from 7 Jun to 8 Jun
£137
7 Jun - 8 Jun
includes taxes & fees
9/10 Wonderful! (2,623 reviews)
"The room is clean and the bed is so comfortable. We booked the room without bathroom, but even shared bathroom , it was maintained so well."

Reviewed on 27 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 £224 per night from 7 Jun to 8 Jun
£224
7 Jun - 8 Jun
includes taxes & fees
9.2/10 Wonderful! (4,666 reviews)
"The pool was not open and we did not find out until after we arrived"

Reviewed on 27 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chestnut Hill travel package cost?
The cheapest Chestnut Hill package is , so your dream holiday can become a reality — without breaking the bank. Bundle flights, hotels and car rentals to customize a package that matches your travelling style.
If I'm not able to travel, can I cancel my Chestnut Hill travel package?
It is possible to cancel your Chestnut Hill booking if your travel plans have changed. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to change or cancel free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
How do I get a cheap travel package to Chestnut Hill?
Track down flights that fit in with your schedule, add a hotel to your booking and watch the savings stack up with a Chestnut Hill travel package. It's as easy as that! From flights and hotels to rental cars and tours, Expedia is where your cheap getaway begins. And with over 550 airlines and 1,000,000 hotels around the globe to pick from, you won't be short of choice.
Does Expedia offer Book Now, Pay Later Chestnut Hill holidays?
Expedia has joined forces with online lender Klarna to make your next trip a little easier on the wallet. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to spend while you're away. Klarna has several payment plans to pick from, so you're sure to find one that fits into your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna can help. Paying in easy monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Consider this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: When you come across an incredible deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in Chestnut Hill?
A holiday in Chestnut Hill wouldn't be complete without visiting Boston College, St. Elizabeths Medical Centre and Brighton Music Hall. Spend your evenings near these popular sights and make sightseeing simple.
What are the top hotels in Chestnut Hill?
Make a reservation at Boston Park Plaza. It's one of the area's most popular properties. Another reputable option in Chestnut Hill is Embassy Suites Boston Logan Airport.
How far in advance should I book my Chestnut Hill holiday?
While not all airlines advertise ticket prices early, customers are usually able to look up international flights on Expedia up to a year in advance. This is when you'll score some fantastic bargains. If you're booking at the last minute, there's a chance you could get lucky. Discounted prices occasionally become available just weeks before departure.
What does an Expedia Chestnut Hill travel package include?
Expedia has all you need to organise your Chestnut Hill escape, but what goes into your package is up to you. Choose from a combination of hotels, flights and rental cars. Searching for a few activities to keep you entertained? Once you've made your booking, you can add them on too. Whatever your style, there's a package to meet your needs.
What should I know before booking a Chestnut Hill travel package?
So many places to venture to, so many things to see. With a travel package, you'll be able to afford more of them. Bundle your flights, hotels and rental cars and enjoy big savings.
Can I choose my airline with a Chestnut Hill Expedia travel package?
Yes, of course. Expedia has access to more than 550 partner airlines around the world, so fly with the carrier that fits your budget and travelling style.

Popular places to visit

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
Harvard University

Harvard University

4.5/5(104 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common

Boston Common

4.5/5(206 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

£42
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

£58
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

£40
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
See all activities in Boston

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.