Brookline Vacation Packages

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Top Brookline Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was CA $1,531, price is now CA $1,331 per person
CA $1,331
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rutland (RUT)
No reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was CA $1,710, price is now CA $1,441 per person
CA $1,441
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rutland (RUT)
9.2/10 Wonderful! (1,002 reviews)
I really enjoyed the heated pool

Reviewed on Jun 29, 2026

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was CA $1,844, price is now CA $1,644 per person
CA $1,644
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rutland (RUT)
9/10 Wonderful! (99 reviews)
The lock situation on the door to my cabin was concerning. The key was required to lock it from both the inside and the outside (presenting a hazard if I needed to escape quickly), and there was no deadbolt. There was another lock that had a keyhole on both the inside and outside, but my key did not work on it. As a single woman staying on the property entirely alone in the off season, I felt the need to barricade my door each night to ensure nobody could get in, since I couldn't deadbolt it.

Reviewed on Jun 18, 2026

Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was CA $1,539, price is now CA $1,376 per person
CA $1,376
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rutland (RUT)
9.4/10 Exceptional! (681 reviews)

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
Price was CA $1,594, price is now CA $1,453 per person
CA $1,453
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rutland (RUT)
9.4/10 Exceptional! (1,226 reviews)
The staff was so helpful and friendly and the room was very cute. Breakfast was great and the property was quiet and well maintained. The only complaint I have was one of the mattresses in our room was very loud and uncomfortable. Overall a very pleasant stay.

Reviewed on Jul 1, 2026

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Brookline Hotel Deals

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jul 12 to Jul 13
CA $155
CA $168 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Rooms were clean and updated. Breakfast was very good. Will be back next year...."

Reviewed on Jul 2, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Jul 5 to Jul 6
CA $181
CA $196 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"It was average but not worth the cost"

Reviewed on Jun 30, 2026

Best Western Plus Keene Hotel
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Fully refundable
The price is CA $219 per night from Jul 6 to Jul 7
CA $219
CA $262 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (284 reviews)
"Lovely resort although the pool is closed until October. Beautiful, peaceful property. 300+ rooms! Music on patio with s’mores was fun. Karen was very nice and helpful. Only negative it is 15 miles from town and not a lot to do!"

Reviewed on Jun 29, 2026

Grand Summit Resort, A Vail Resorts Property
See all 1,758 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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What to do in Brookline

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

CA $24
per traveller
Vermont RT 100 App-Guided Driving Audio Tour
Mindful Forest Escape: Rebalance, reflect and connect

Mindful Forest Escape: Rebalance, reflect and connect

CA $131
per adult
Mindful Forest Escape: Rebalance, reflect and connect
See all activities in Brookline

Frequently asked questions

How much does a Brookline vacation package cost?
You'll find cheap prices from CA $1,331 on Expedia for your Brookline break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Brookline costs.
What are the cheapest months to go to Brookline?
Plan your trip for the off-peak season and you're likely to score cheap Brookline vacation packages. Keep in mind that school vacation periods and local events and festivals can have an impact on prices, so do some research before booking.
How many days is enough for Brookline?
Generally, a handful of days is enough to tick off the main sights during your Brookline vacation. However, if you prefer to have more time to rest or take day tours, consider extending your trip.
How to find the best Brookline package deals?
Finding a cheap Brookline package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Brookline package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Brookline vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights individually. Better still, you can tailor your Brookline escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Brookline?
If you're planning an impromptu Brookline trip, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Brookline?

  1. Choose when to get away: Check your diary and get packing. Your preferred time of year and the available activities will also help you decide when to vacation in Brookline.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and dining out to flights and experiences. Your accommodations will likely be the biggest expense during your trip to Brookline.
  3. Decide how long to go away for: Now that you know more about Brookline, you can work out the ideal length of your break. Put together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your accommodations and airfare: After you've settled on your dates and duration, book the right Brookline vacation package for you.

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