Dorchester Holidays from AU$2,846

Book a Hotel + Flight or Car together to unlock savings

Your Dorchester Holiday

Packed with charm and personality, Dorchester offers everything from nature to dining. Experience the wonders of this neighbourhood the easy way with a personalised Dorchester holiday package. When it's time to explore the sights, you'll find loads of big-name attractions nearby including Boston Museum of Fine Arts, Northeastern University and John F. Kennedy Presidential Library and Museum. Tick off one, two or all during your trip to Dorchester. Don't just think about it — make it happen! Book your ideal Dorchester holiday with Expedia and experience travel your way.

Top Holiday Package Deals in Dorchester

Price found within the past 48 hours. Click for updated prices.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Price was AU$4,000, price is now AU$2,846 per person
AU$2,846
per person
12 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul. 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was AU$7,028, price is now AU$4,364 per person
AU$4,364
per person
12 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
The staff were amazing, rooms were spotless and with wonderful amenities and special touches.

Reviewed on 22 Aug. 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was AU$6,212, price is now AU$3,972 per person
AU$3,972
per person
12 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on 20 Aug. 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was AU$7,836, price is now AU$5,450 per person
AU$5,450
per person
12 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
The Langham is a wonderful, luxurious family hotel. The staff were absolutely lovely and made a fuss over our young daughter which seems rare at hotels these days. The location of the hotel is also fantastic, as it's within walking distance to both the Boston Children’s Museum and the aquarium. The indoor pool was a fantastic added bonus that our family thoroughly enjoyed. We were so impressed with our experience that we will definitely be staying at The Langham again the next time we are in Boston.

Reviewed on 21 Aug. 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was AU$4,045, price is now AU$2,925 per person
AU$2,925
per person
12 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Heather was unbelievable in every way. Because of her past excellent service we returned!! She makes this hotel experience a true pleasure. Thank you Heather for your kind and gracious assistance.

Reviewed on 21 Aug. 2025

Our guide on where to stay in Dorchester

Find the best Dorchester areas and neighborhoods for the activities you enjoy most. Learn more about Dorchester
Downtown Boston showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(17 area reviews)

This is Boston’s business district, now and back when the city was just starting.

Find hotels in Downtown Boston

Our pick of the best Dorchester Hotel Deals

Ramada by Wyndham Boston

Ramada by Wyndham Boston

2.5 out of 5
800 Morrissey Blvd, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$189 per night from 2 Sept to 3 Sept
AU$189
2 Sept - 3 Sept
includes taxes & fees
6.6/10 (1,339 reviews)
"Nice and clean"

Reviewed on 20 Aug. 2025

Ramada by Wyndham Boston
DoubleTree by Hilton Hotel Boston Bayside

DoubleTree by Hilton Hotel Boston Bayside

4 out of 5
240 Mount Vernon Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$249 per night from 1 Sept to 2 Sept
AU$249
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,358 reviews)
"Great location to the T"

Reviewed on 13 Aug. 2025

DoubleTree by Hilton Hotel Boston Bayside
Home2 Suites by Hilton Boston South Bay

Home2 Suites by Hilton Boston South Bay

3 out of 5
15 JAN KARSKI WAY, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$384 per night from 21 Sept to 22 Sept
AU$384
21 Sept - 22 Sept
includes taxes & fees
8.8/10 Excellent! (807 reviews)
"Amazing hotel, Nice stay, Friendly staff and Great breakfast!"

Reviewed on 18 Aug. 2025

Home2 Suites by Hilton Boston South Bay
See all 3,870 properties in Dorchester
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
All Inclusive Holidays
Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Dorchester holiday package cost?
Maybe less than you might think — from only AU$2,846, actually! By combining flights, hotels and car rentals into your own custom-built travel package, your Dorchester escape is just clicks away.
How do I get a cheap travel package to Dorchester?
Our Dorchester holiday packages promise plenty of savings for the savvy explorer. For the best deals, simply bundle your flights, hotels and extras (including tours) into an affordable package. But great bargains are only the start of your next amazing adventure. When you book with Expedia, and you'll have over 550 airlines and 1 000 000 hotels globally to choose from. No matter your style or budget, there's a package that's perfect for you.
Where should I stay in Dorchester?
Holiday Makers come from all over the world to see Fenway Park and TD Garden in Dorchester. Stay within a stone's throw of these must-see attractions to make sightseeing easy.
What are the top hotels in Dorchester?
Lg Suite For Up To 6 Ppl/1 Floor and Home2 Suites by Hilton Boston South Bay are among the most well-known hotels in Dorchester. Why not take a look at the facilities and rates at each and then make up your mind?
How far in advance should I book my Dorchester holiday?
While not all air carriers advertise ticket prices early, you can normally look up international fares on Expedia up to 12 months in advance. This is the time when you'll bag some incredible deals. If you're booking late, you may still be in luck. Sometimes the cheapest prices become available a few weeks before departure.
What does an Expedia Dorchester travel package include?
You can select from any combination of rental cars, hotels and flights. Once you've made your booking, you can add some experiences and activities. Want to pick your fare class? That's also easy to do. The choice is yours when it comes to creating your ideal Dorchester escape.
What should I know before booking a Dorchester travel package?
Locking in all the parts of your holiday together is an excellent way to save. Bundle your car rentals, airfares and hotels into a convenient package. But it's not just hotels. Expedia features all sorts of properties, including holiday homes such as beachfront villas and serviced residences. You've got choices galore!
Can I choose my airline with a Dorchester Expedia holiday package?
You can, and with over 550 airlines to select from throughout the world, you have loads of choice. Search the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Dorchester holiday package?
Your situation can change unexpectedly, so yes. You may be able to cancel or amend your Dorchester holiday package at no cost within 24 hours of booking. For bookings older than that, you can still make the necessary changes, but your car rental company, hotel or airline may charge a fee. Need more information? Check out our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Dorchester

John F. Kennedy Presidential Library and Museum

John F. Kennedy Presidential Library and Museum

You can study the exhibits at John F. Kennedy Presidential Library and Museum, a museum with a storied past, during your trip to Boston. Experience the fascinating museums or attend a sporting event in this vibrant area.

John F. Kennedy Presidential Library and Museum

Activities

Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace

Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace

AU$15
per traveller
84% of travellers recommend
Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

AU$107
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
2-Day Secret Cavern+Niagara Falls Tou

Niagara Falls(US) 2-Day Tour from Boston

AU$75
per adult
Niagara Falls(US) 2-Day Tour from Boston
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.