Dorchester Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Jul 15 - Jul 24

    Hotel Ivy Boston Common + Flight

    Bay Village
    9 nights
    2.5 star property
    8.4/10 - Very good (1,474 reviews)
    "My stay at Hotel Ivy was great! The staff was helpful and friendly, and my room was cozy and charming. The location of this hotel is great for walking around historic Boston. I would definitely stay again or recommend to others."
    Reviewed June 1, 2026
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    €2,772
    €1,736
    per traveller
    found 1 day ago
    Hotel Ivy Boston Common
  • Jul 15 - Jul 24

    Boston Harbor Hotel + Flight

    North End
    9 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "Wonderful classic harbor front hotel. Very nice front desk. Would stay again"
    Reviewed May 25, 2026
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    €5,172
    €2,931
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • Jul 15 - Jul 24

    Fairmont Copley Plaza, Boston + Flight

    Back Bay
    9 nights
    4.5 star property
    9.0/10 - Wonderful (1,245 reviews)
    "I recently stayed at the Fairmont Boston and unfortunately the property felt very outdated and not well maintained compared to what I expected from a Fairmont hotel. While the location is convenient and the staff were generally polite, the overall condition of the hotel needs significant updates. The rooms showed noticeable wear and tear, including older furniture, dated décor, and areas that did not feel particularly clean or refreshed. The hallways and common areas also felt tired and lacked..."
    Reviewed May 29, 2026
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    €3,638
    €2,389
    per traveller
    found 1 day ago
    Fairmont Copley Plaza, Boston
  • Jul 15 - Jul 24

    Raffles Boston + Flight

    Back Bay
    9 nights
    5.0 star property
    9.6/10 - Exceptional (268 reviews)
    "This was an interesting hotel and if you have any experience of the raffles brand elsewhere then I would recommend be prepared. The venue is central but overlooking an 8storey multi story car park and rather cramp rooms was not really value add. The suite on the other hand in higher floors were. A butler system which I must say working off some mediocre phone prompts just doesn’t cut it . One looses the will to live when saying I need a shaving kit and al you get back is “is there something else..."
    Reviewed May 28, 2026
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    €5,270
    €3,590
    per traveller
    found 1 day ago
    Raffles Boston
  • Jul 15 - Jul 24

    Eurostars The Boxer + Flight

    West End
    9 nights
    4.0 star property
    8.8/10 - Excellent (1,509 reviews)
    "For the price they charge, it’s not worth it"
    Reviewed June 1, 2026
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    €2,853
    €1,953
    per traveller
    found 1 day ago
    Eurostars The Boxer

Where to stay in Dorchester

Find the best Dorchester areas and neighborhoods for the activities you enjoy most. Learn more about Dorchester

Top hotels in Dorchester

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 €162 per night from 4 Jun to 5 Jun
€162
4 Jun - 5 Jun
includes taxes & fees
6.8/10 (1,747 reviews)
"Clean"

Reviewed on 1 Jun 2026

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 €183 per night from 4 Jun to 5 Jun
€183
4 Jun - 5 Jun
includes taxes & fees
8.4/10 Very Good! (1,482 reviews)
"The food at the bar was great!"

Reviewed on 1 Jun 2026

DoubleTree by Hilton Hotel Boston Bayside
Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston

2 out of 5
60 Ridgewood St Boston MA
The price is €107 per night from 7 Jun to 8 Jun
€107
7 Jun - 8 Jun
includes taxes & fees
8.2/10 Very Good! (50 reviews)
"I got as far as driving into the neighborhood and decided it did not feel safe and would not be comfortable parking my vehicle. I drove the 2.5 hours home rather than stay there"

Reviewed on 28 May 2026

Homestay In Fields Corner Area Boston
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 , 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 rentals 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.

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.