Brookline Vacations from $378
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Your Brookline Vacation
Our vacation packages to Brookline allow you to create your own adventure. Tailor your getaway to suit your needs and interests and make every moment count in this fabulous city. Every trip to Brookline needs a well-crafted itinerary. Fill yours with leading attractions like Silver Lake State Park, Beaver Brook Reservation and Andres Institute of Art. Check out Expedia's wide range of travel options and book your perfect vacation to Brookline today.
The Latest Brookline vacation packages
Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College
Save 100% on your flight
Price was $585, price is now $378 per person
$378
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (1,169 reviews)
I requested a room with two beds. The second bed was a folding chair that, when unfolded, blocked access to the refrigerator and the side of the bed. The room is too small for 3 people.
Reviewed on Jul 6, 2026
The Coach House
Price was $1,816, price is now $982 per person
$982
per person
Sep 5 - Sep 8
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (182 reviews)
This was my first time staying at a boutique hotel and it was a great choice. Not only was the price great, but the room was a good size and I enjoyed the snacks and toiletries. It was also very quiet— I slept very well. The Coach House is about a 20 minute walk (5-10 minute Uber) into the town square. The weather was great so I enjoyed the walks. Water was hot and pressure good.
Reviewed on Jun 15, 2026
Boston Lodge and Suites
Dorchester
Save 100% on your flight
Price was $1,429, price is now $899 per person
$899
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Save 100% on your flight
Price was $5,601, price is now $3,666 per person
$3,666
per person
Aug 12 - Aug 17
found 23 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended.
Tim Lawler
Reviewed on Oct 8, 2025
Stay near popular Brookline attractions
Brookline Hotel Deals
Great Wolf Lodge Boston / Fitchburg, MA
150 Great Wolf Dr Fitchburg MA
$149 nightly
The price is $166 total per night from Jul 7 to Jul 8
$166 total
Jul 7 - Jul 8
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
"I bought hamburgers for the family at Buckets. The sandwiches arrived cold when I asked to exchange them. The employee mocked, smiled, and took 6 minutes to return the food. And when the snack arrived, he had burnt the bacon."
Reviewed on Jul 5, 2026
Comfort Inn Manchester Airport
298 Queen City Ave Manchester NH
Fully refundable
$110 nightly
The price is $119 total per night from Jul 13 to Jul 14
$119 total
Jul 13 - Jul 14
Total with taxes and fees
8.2/10 Very Good! (1,006 reviews)
"¥"
Reviewed on Jul 6, 2026
DoubleTree by Hilton Manchester Downtown
700 Elm St. Manchester NH
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $137 total per night from Jul 19 to Jul 20
$137 total
Jul 19 - Jul 20
Total with taxes and fees
9.2/10 Wonderful! (1,213 reviews)
"Great staff, great location, very nice property."
Reviewed on Jul 1, 2026
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.
Find the Best Brookline Vacation Packages
Brookline Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Manchester-Boston Regional Airport (MHT) |
Population | 4,700 |
Top Sights | Anheuser-Busch Brewery, LaBelle Winery and Fun World |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
