Chestnut Hill Holidays from £928

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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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was £1,561, price is now £928 per person
£928
per person
14 Sept - 18 Sept
found 7 hours ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on 19 May 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,122, price is now £1,411 per person
£1,411
per person
24 Aug - 28 Aug
found 11 hours ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
9.8/10 Exceptional! (1,015 reviews)
Great location and very helpful staff

Reviewed on 16 Jul 2026

The Inn at Longwood Medical

The Inn at Longwood Medical

3.5 out of 5
Fenway–Kenmore
Save 100% on your flight
Price was £1,627, price is now £1,132 per person
£1,132
per person
10 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LON) to Boston (BOS)
8.4/10 Very good! (1,006 reviews)
Room was very clean. No issues.

Reviewed on 20 Jul 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was £2,468, price is now £1,748 per person
£1,748
per person
2 Oct - 9 Oct
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (262 reviews)
This Inn is a beautiful old building with a long history. It is located within easy walking distance of downtown Lexington with all its history. The Inn had wonderful rooms, a great staff and a top rate restaurant all in one place. Highly recommend!

Reviewed on 13 Jul 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was £1,856, price is now £1,366 per person
£1,366
per person
4 Sept - 9 Sept
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The property was well maintained and close to good restaurants. We had a cooked breakfast every day.

Reviewed on 16 Jul 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
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

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 £198 per night from 26 Jul to 27 Jul
£198
26 Jul - 27 Jul
includes taxes & fees
9.6/10 Exceptional! (4,589 reviews)
"This was such a pleasant stay! The staff are over the top helpful and so kind! The room was just perfect with a great view of the harbor. Valet was seamless. The restaurant was good!! Wonderful stay in Boston!"

Reviewed on 21 Jul 2026

Seaport Hotel Boston
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 £238 per night from 31 Jul to 1 Aug
£238
31 Jul - 1 Aug
includes taxes & fees
9.2/10 Wonderful! (4,804 reviews)
"It was greatl"

Reviewed on 20 Jul 2026

Omni Boston Hotel at the Seaport
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 £124 per night from 16 Aug to 17 Aug
£124
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (2,755 reviews)
"great hotel, accommodated a late check out which was very appreciated! would stay again!"

Reviewed on 20 Jul 2026

The Revolution Hotel
See all 3,964 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.
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Frequently asked questions

How much does a Chestnut Hill travel package cost?
The cheapest Chestnut Hill package is £928, 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.

Stay near popular Chestnut Hill attractions

McMullen Museum

6.0/10 (1 review)
This Boston College treasure houses over 5,000 artworks spanning diverse periods and cultures. Explore the serene galleries on Sunday afternoons for free docent-led tours of current exhibitions.
See properties

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

£39
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

£36
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

£60
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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.