Dudley Square Holidays from £1,621

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Your Dudley Square Holiday

Reserving a Dudley Square holiday package is a superb way to become acquainted with this neighbourhood. From its must-visit places to its little-known secrets, you won't be short of new adventures. Start your trip to Dudley Square with a visit to nearby attractions such as Fenway Park, Boston Common and Faneuil Hall Marketplace. Whatever your dream Dudley Square holiday looks like, you can turn it into reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
2 Sep - 9 Sep
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
8.6/10 Excellent! (1,014 reviews)
Beautiful property and the staff always went above and beyond to accommodate our needs

Reviewed on 18 Jun 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
2 Sep - 9 Sep
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.4/10 Exceptional! (275 reviews)
EVERYTHING is thought out. Service is “old world”. Attention to details is magnificent. What’s there not to like.

Reviewed on 9 Jun 2024

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
2 Sep - 9 Sep
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.2/10 Wonderful! (263 reviews)
Have tried several Boston hotels over the years but after staying at the Newbury, it will be the only place I stay in Boston from now on.

Reviewed on 16 Jun 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
2 Sep - 9 Sep
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (283 reviews)
This was one of the best hotel experiences I've had. The staff goes above and beyond to make you feel welcomed. From the Tates cookies and sparkling water available, to the water bottles at the end of the night, they really pay attention to small details, making it a great experience. The rooms were clean and roomy. We ended up walking the entire time in Boston since the hotel was at a great location, but if you plan on driving, keep in mind that you have to call ahead of time to access your car. Would definitely stay again!

Reviewed on 28 May 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
2 Sep - 9 Sep
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.4/10 Exceptional! (36 reviews)
Beautiful hotel, flowers in All areas. Staff was superb. Two very minor issue - no fan for toilet area, hot water in shower takes a bit. Doesn’t distract from my overall rating. Easily a come back recommendation

Reviewed on 29 May 2024

Where to stay in Dudley Square

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

Downtown Boston

4.5/5(94 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

Top hotels in Dudley Square

The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA
The price is £155 per night from 30 Jun to 1 Jul
£155
per night
30 Jun - 1 Jul
8.6/10 Excellent! (1,553 reviews)
A great hotel experience at a fair price.
"I enjoyed my stay at the Revolution Hotel very much. It's located in a nice part of Boston where you can easily access public transportation or walk."

Reviewed on 17 Jun 2024

The Revolution Hotel
Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £212 per night from 3 Jul to 4 Jul
£212
per night
3 Jul - 4 Jul
9/10 Wonderful! (2,213 reviews)
Coffee stains
"Sheets looked like they had coffee stains. Otherwise room was in good condition"

Reviewed on 18 Jun 2024

Omni Boston Hotel at the Seaport
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £195 per night from 4 Jul to 5 Jul
£195
per night
4 Jul - 5 Jul
8.8/10 Excellent! (2,688 reviews)
"Great check in and helpful staff throughout our stay. This is one of the oldest hotels and must be appreciated for its storied history. Very convenient location for visiting downtown historical sites. We had a lovely time"

Reviewed on 19 Jun 2024

Omni Parker House
See all 3,197 properties in Dudley Square
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

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Dudley Square travel package cost?
Get set to book, because a getaway to Dudley Square starts from only £1,621. When you bundle your flights, hotels and car rentals into a package, you’ll score the best deals.
If I'm not able to travel, can I cancel my Dudley Square travel package?
Your situation can change in the blink of an eye, so yes. You may be able to change or cancel your Dudley Square travel package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make the necessary changes, but your airline, hotel or car rental company may impose a charge. Want more information? Look up our Customer Service Portal. We’re here to help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Dudley Square?
You’ll save loads of cash if you bundle your car rentals, flights and hotels into a Dudley Square travel package. Sometimes cheap means fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels across the globe, so you’ll always have plenty of variety to choose from. Want to save even more? Add some fun activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Dudley Square holidays?
Expedia has teamed up with online lender Klarna to make your next trip easier on your bank balance. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more cash to play with while you’re away. Klarna has several payment plans to pick from, so you’re sure to find something that works with your budget. Consider these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna’s monthly instalment plans. If paying bite-sized amounts each month sounds right for you, choose this option during the checkout process.
  • Pay in instalments holidays: If you’d like to pay off your getaway in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you spot an incredible deal but don’t have the full amount yet, Klarna’s low deposit holiday plan will help you lock in your getaway.

Where should I stay in Dudley Square?
Urban explorers come from all corners of the globe to experience Fenway Park and TD Garden in Dudley Square. Book a hotel within a stone’s throw of these awesome attractions to make sightseeing a breeze.
What are the top hotels in Dudley Square?
Boston Park Plaza and Embassy Suites Boston Logan Airport are two of the most well-known properties in Dudley Square. Why not have a look at the rates and facilities at each and then make up your mind?
How far in advance should I book my Dudley Square holiday?
While prices change frequently, we generally suggest booking your spot as soon as possible. Many international fares can be found on Expedia up to a year in advance. If you’re booking last minute, you might still be in luck. Cheap tickets to Dudley Square occasionally appear only weeks before departure.
What does an Expedia Dudley Square travel package include?
Flights, car rentals and hotels — we connect you to all the best deals. All you have to do is decide on your favourite combination. After you’ve made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it easy to craft an awesome Dudley Square holiday.
What should I know before booking a Dudley Square travel package?
You’ll land amazing savings when you bundle your hotels, flights and rental cars into a travel package. Not just that, booking everything in one place will make your trip planning easier. So why waste your time or money? Whether you’re putting together a fancy romantic getaway or a budget family adventure, explore our travel packages today.
Can I choose my airline with a Dudley Square Expedia travel package?
Yes, and with more than 550 airlines to pick from around the world, you’re spoiled for choice. Scroll through the available options and see which airline best fits your needs and budget.

Popular places to visit

Image for Fenway Park

Fenway Park

4.5/5(61 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Image for Harvard University

Harvard University

4.5/5(102 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Image for Gillette Stadium

Gillette Stadium

3/5(2 reviews)

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theatre scene and great live music.

Gillette Stadium

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£63
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

£24
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

£172
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Boston

More trip options

* 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.