Dorchester Holidays from NZ$3,222

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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
per person
29 Oct - 1 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul. 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
29 Oct - 1 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on 5 Aug. 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
29 Oct - 1 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Very convenient boutique hotel

Reviewed on 5 Aug. 2025

The Hotel Salem

The Hotel Salem

3 out of 5
per person
29 Oct - 1 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.2/10 Wonderful! (1,013 reviews)
Check in was friendly and quick, staff.was helpful with transportation options and suggestions for activities, dining and shopping. The hotel is literally next to shopping, dining and short walking distance to popular attractions.

Reviewed on 7 Aug. 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
29 Oct - 1 Nov
found 5 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.6/10 Exceptional! (428 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.

Reviewed on 25 Jul. 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)

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

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 NZ$222 per night from 4 Sept to 5 Sept
NZ$222
4 Sept - 5 Sept
includes taxes & fees
6.6/10 (1,311 reviews)
"Nice hoter"

Reviewed on 6 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 NZ$281 per night from 17 Aug to 18 Aug
NZ$281
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,354 reviews)
"The staff was all very friendly awesome transport to local restaurants with their shuttle driver Sammy. let us check in early.will definitely be coming back next time we go to Boston. the bartender was good made me a drink they don't normally do."

Reviewed on 5 Aug. 2025

DoubleTree by Hilton Hotel Boston Bayside
Courtyard by Marriott Boston-South Boston

Courtyard by Marriott Boston-South Boston

3 out of 5
63 R Boston St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NZ$311 per night from 1 Sept to 2 Sept
NZ$311
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Our room had apparently been recently refurbished. Comfortable and clean and everything worked (though the lights took a little figuring out). The elevator was a little slow i think because it was the only one, and swiping the room card was a pain. But overall very good."

Reviewed on 5 Aug. 2025

Courtyard by Marriott Boston-South Boston
See all 3,871 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.

Frequently asked questions

How much does a Dorchester holiday package cost?
Maybe less than you might think — from only NZ$3,222, 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

University of Massachusetts Boston

Enjoy the student vibe when you visit University of Massachusetts Boston during your trip to Boston. Experience the fascinating museums or attend a sporting event in this walkable area.

University of Massachusetts Boston

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

NZ$17
per traveller
84% of travellers recommend
Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

NZ$131
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

NZ$117
per adult
86% 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.