Brookline Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.

Top Brookline Vacation Deals

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
Price was CA $1,217, price is now CA $854 per person
CA $854
per person
Aug 18 - Aug 21
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (1,254 reviews)
The staff were all super kind and helpful. I really enjoyed the old school and glam aspect of the hotel but did lead to a few things. For example a gap under the door meant a bright light in the room which hinder sleep, room had slight smell of smoke and sound of water dripping. Great location, safe and clean.

Reviewed on Jul 12, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,482, price is now CA $1,929 per person
CA $1,929
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,377, price is now CA $1,445 per person
CA $1,445
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great 👍

Reviewed on Jul 11, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Price was CA $10,261, price is now CA $6,763 per person
CA $6,763
per person
Aug 17 - Aug 24
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
10/10 Exceptional! (9 reviews)
It was an amazing relaxing place. Very family friendly

Reviewed on Jul 12, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $1,674, price is now CA $1,136 per person
CA $1,136
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

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Brookline Hotel Deals

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
The price is CA $232 per night from Jul 14 to Jul 15
CA $232
CA $259 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (1,023 reviews)
"Clean room fun for kids"

Reviewed on Jul 13, 2026

Great Wolf Lodge Boston / Fitchburg, MA
Comfort Inn Manchester Airport

Comfort Inn Manchester Airport

2.5 out of 5
298 Queen City Ave Manchester NH
Fully refundable
The price is CA $166 per night from Jul 23 to Jul 24
CA $166
CA $180 total
Jul 23 - Jul 24
includes taxes & fees
8.2/10 Very good! (1,016 reviews)
"Staff was helpful and providing some fruit and yogurt before I left at 3 AM for the airport"

Reviewed on Jul 12, 2026

Comfort Inn Manchester Airport
Best Western Plus Executive Court Inn & Conference Center

Best Western Plus Executive Court Inn & Conference Center

3 out of 5
13500 S Willow St Manchester NH
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Jul 19 to Jul 20
CA $142
CA $154 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (1,407 reviews)
"Waited almost 15 minutes to check in because the front desk staff were not present. Also, the floor in the room as dirty because my white socks are black on the bottom. The sink drained super slow, lightbulb above the hot tub in the room was flickering bad and the room is overdue for a face lift. ..."

Reviewed on Jul 12, 2026

Best Western Plus Executive Court Inn & Conference Center
See all 394 properties in 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.
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Stay near popular Brookline attractions

Andres Institute of Art

You can spend an afternoon exploring the galleries in Andres Institute of Art during your travels in Brookline. You can attend a sporting event while in the area.
See properties

Frequently asked questions

How much does a Brookline vacation package cost?
You'll find cheap prices from CA $854 on Expedia for your Brookline break. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Brookline costs.
What are the cheapest months to go to Brookline?
January, February and March are the best times to search for cheap Brookline vacation packages. Choosing to travel in quieter months means you'll typically find lower prices on flights and hotels.
How many days is enough for Brookline?
With a well-organized schedule, you can easily hit the most popular Brookline attractions in a handful of days. But if you want to discover hidden gems or go on day tours, think about booking your Brookline vacation for longer.
How to find the best Brookline package deals?
Bagging a cheap Brookline package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, add a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Brookline package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Brookline vacation as a package?
You can enjoy significant savings on your next Brookline getaway by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Brookline?
If you have your Brookline vacation dates confirmed, book as soon as you can to grab some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Brookline?

  1. Choose when to go: Check your diary and get packing. Your preferred time of year and the activities on offer will also help you decide when to vacation in Brookline.
  2. Set a budget: Consider expenses such as flights, transportation and food when working out how much to set aside for your trip to Brookline. Then, pick a property that works with your budget, whether that's an economical stay or a more upscale retreat.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to experience in Brookline. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Brookline vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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