South Brookline Holidays

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Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
30 Aug - 1 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (2,977 reviews)
Be mindful of what time you are checking in, it can get busy. Other than that it’s EXCELLENT!

Reviewed on 19 Jun 2025

Centerboard

Centerboard

2 out of 5
Nantucket Town
Save 100% on your flight
per person
30 Aug - 4 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (66 reviews)
We loved everything about Centerboard--the silence, the comfort of the room, the large shower (don't forget to sing in the shower), the short distance to everything, including the Steamship Authority. It was simple to move in and out and had the room key waiting for us. We will definitely return on our next trip to Nantucket. Can't wait!!

Reviewed on 31 May 2025

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
per person
30 Aug - 4 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (167 reviews)
Really enjoyed our "By the Sea". Our room, one of the less expensive rooms with a view of the parking lot and another building was, nevertheless, very comfortable. Excellent king bed was, efficient, quiet AC, large enough to move around. The location -right on the beach with a sea-view breakfast room.Breakfast was terrific - freshly made muffins, eggs, meats, fresh fruit. A good value.

Reviewed on 15 Jun 2025

Life House, Nantucket

Life House, Nantucket

3.5 out of 5
Nantucket Town
Save 100% on your flight
per person
30 Aug - 4 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.2/10 Very Good! (51 reviews)
Nice hotel but rooms are very small and our bathroom was not attached to room so hard if you get up a lot at night to go to the restroom.

Reviewed on 17 Sep 2024

Chatham Tides

Chatham Tides

2.5 out of 5
per person
30 Aug - 4 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (586 reviews)
Beautiful spot, instantly made me feel relaxed. Staff was wonderful & tje room was adorable and very clean

Reviewed on 10 Jun 2025

Where to stay in South Brookline

Find the best South Brookline areas and neighborhoods for the activities you enjoy most. Learn more about South Brookline
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)

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Harbor and Boston Massacre Site, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotels in Downtown Boston

Top hotels in South Brookline

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €229 per night from 19 Jul to 20 Jul
€229
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (3,562 reviews)
Doesn’t get better!
"Beautiful hotel with awesome amenities from the pool to restaurants and great location! Only down side is small rooms."

Reviewed on 17 Jun 2025

Omni Boston Hotel at the Seaport
Hilton Boston Back Bay
Hilton Boston Back Bay
4 out of 5
40 Dalton St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €224 per night from 29 Jun to 30 Jun
€224
29 Jun - 30 Jun
includes taxes & fees
8.4/10 Very Good! (1,118 reviews)
"Everything was excellent. The breakfast buffet was fresh and delicious with a wide variety of options. I especially enjoyed the made-to-order omelets. I would definitely stay here again and highly recommend it to anyone visiting the area."

Reviewed on 14 Jun 2025

Hilton Boston Back Bay
Copley Square Hotel, a FOUND Hotel
Copley Square Hotel, a FOUND Hotel
4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €144 per night from 2 Jul to 3 Jul
€144
2 Jul - 3 Jul
includes taxes & fees
8.4/10 Very Good! (3,700 reviews)
"The hotel staff was very accommodating, wouldn’t recommend for family to stay here, but probably as a business trip or a couple visiting the city."

Reviewed on 16 Jun 2025

Copley Square Hotel, a FOUND Hotel
See all 3,490 properties in South Brookline
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 South Brookline holiday package cost?
The most affordable South Brookline holiday package is €708, so your dream holiday can become a reality --- without spending an arm and a leg. Combine flights, hotels and car rentals to tailor a package that suits you.
How do I get a cheap travel package to South Brookline?
Our South Brookline holiday packages mean plenty of savings for the savvy explorer. For the best deals, simply combine your flights, hotels and extras (including tours) into an affordable package. But bargain prices are just the beginning of your next big adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 hotel options around the world to select from. Whatever your budget or style, there's a package here just for you.
Where should I stay in South Brookline?
There's so much to see in South Brookline, so spend your evenings close to its top attractions and spend more time sightseeing. Osher Clinical Centre is one spot that should be on your itinerary.
How far in advance should I book my South Brookline holiday?
It's hard to pick the ideal time for airfares, but we generally say the earlier, the better. Plenty of international flights on Expedia become available up to 12 months in advance. If you're booking last minute, don't fret. Discounted prices appear from time to time within a few weeks of departure dates.
What does an Expedia South Brookline travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your perfect South Brookline trip. You can also add on tours and activities once you've made your booking. You're in charge! When you bundle your bookings with Expedia, you'll get access to discounts you won't find elsewhere.
What should I know before booking a South Brookline travel package?
When you book your flights, hotels and car rentals together, you'll nab fantastic discounts. Whether you're planning a beach break in a villa or want to stay in a comfortable hotel in the city, Expedia can help make it happen.
Can I choose my airline with a South Brookline Expedia holiday package?
Yes --- and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our holiday packages give you the flexibility to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my South Brookline holiday package?
Your situation can change unexpectedly, so yes. You may be able to cancel or alter your South Brookline holiday package at no cost if you've booked in the last 24 hours. For bookings older than that, you can still make changes, but your car rental company, hotel or airline may charge a fee. Need more information? Have a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Popular places to visit

Fenway Park showing night scenes and a sporting event as well as a large group of people

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
Harvard University which includes heritage architecture and a city

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
Copley Square

Copley Square

4/5(16 reviews)

Explore some of Boston’s finest buildings, educational and arts institutions, and shopping, or simply find a patch of grass and relax.

Copley Square

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

€70
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

€48
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

€24
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.