Chestnut Hill Holiday Packages

Save when you book Chestnut Hill package deals

Choose two or more items and save on your trip:

Top Chestnut Hill holiday packages

Price found within the past 48 hours. Click for updated prices.
The Bostonian Boston
The Whitney Hotel
The Langham, Boston
Eurostars The Boxer
Fairmont Copley Plaza, Boston

Book your Chestnut Hill holiday

Save some moolah with Wotif.

We can combine your accommodation and flights into a tidy little package.

With the extra funds you can discover even more in Chestnut Hill.

Act now and save up to $245. Also, we can link you up with more than 550 airlines and 665,000 worldwide properties — your ideal holiday is only a couple of clicks away.

Don't waste your precious time trawling the internet when you could be packing. Wotif offers some of the most attractive deals anywhere.

Chestnut Hill Accommodation

Our database lists 90 accommodations in Chestnut Hill. However, none of them are located right in the heart of the neighbourhood. Browse through your options on Wotif — you're sure to find an awesome place not too far away.

If you're after a place with good amenities and services, why not check out the Mandarin Oriental Boston (776 Boylston St) and the Global Luxury Suites at Back Bay (32 Garrison Street)? Both come with excellent reviews and are a hit with many visitors.

Car Hire in Chestnut Hill

A quick taxi drive from Logan International Airport will land you at either Advantage Rent-A-Car (100 Tomahawk Drive) or Enterprise (6 Tomahawk Dr). Whichever you choose, we know you'll find the perfect set of wheels for you.

Easy and convenient — two great words everybody longs to hear while travelling the world. Luckily, Enterprise lives up to them. Only 4 kilometres from the downtown area and featuring a variety of fine vehicles, you'll be dashing off on your next excellent adventure in a flash.

Holidays to Chestnut Hill

Trapped at work dreaming about Chestnut Hill and all the incredible things it has to offer? Take the first step to actually getting there by learning a little bit about it.

Chestnut Hill is around 10 kilometres southwest of the centre of Boston. It's one of the many interesting neighbourhoods you'll find in the Massachusetts state capital.

If you've heard fellow travellers not only go nuts about Chestnut Hill but about Boston in general, then it shouldn't come as a surprise to find out that around 600 000 people call it their home.

Top Chestnut Hill hotels

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 AU$346 per night from 23 Nov to 24 Nov
AU$346
23 Nov - 24 Nov
includes taxes & fees
The Dagny Boston: Luxury hotel with free WiFi and a bar/lounge. Located in the city centre.
High marks across the board - friendly, professional staff, convenient location, and great in-house restaurant.

Reviewed on 8 Nov 2025

Opens in a new windowThe 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
The Revolution Hotel: Pet-friendly hotel with free WiFi and a bar/lounge. Located near a metro station.
Great location, clean room and nice people!

Reviewed on 13 Nov 2025

Opens in a new windowThe 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 AU$304 per night from 27 Nov to 28 Nov
AU$304
27 Nov - 28 Nov
includes taxes & fees
Omni Boston Hotel at the Seaport: Luxury hotel with free WiFi and an outdoor pool. Located near a train station.
Microwave in the room

Reviewed on 11 Nov 2025

Opens in a new windowOmni Boston Hotel at the Seaport
Don't see what you're looking for?
See all available properties in Chestnut Hill
View all properties
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.

More Destinations