Brookline Vacation Packages

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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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Top Brookline Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was CA $832, price is now CA $793 per person
CA $793
per person
Dec 4 - Dec 6
found 13 hours ago
Roundtrip flight included
Detroit (DTT) to Rutland (RUT)
10/10 Exceptional! (38 reviews)

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was CA $875, price is now CA $806 per person
CA $806
per person
Dec 4 - Dec 6
found 13 hours ago
Roundtrip flight included
Detroit (DTT) to Rutland (RUT)
9.4/10 Exceptional! (1,005 reviews)
Lovely staff, great views

Reviewed on Nov 1, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was CA $835, price is now CA $811 per person
CA $811
per person
Dec 4 - Dec 6
found 13 hours ago
Roundtrip flight included
Detroit (DTT) to Rutland (RUT)
9/10 Wonderful! (890 reviews)

Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was CA $988, price is now CA $988 per person
CA $988
per person
Dec 4 - Dec 6
found 13 hours ago
Roundtrip flight included
Detroit (DTT) to Rutland (RUT)
9/10 Wonderful! (127 reviews)
I promise, especially if you’re staying in the condo buildings you will love it

Reviewed on Sep 23, 2026

Ready to book your vacation to Brookline?

 

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Brookline Hotel Deals

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 $222 per night from Nov 23 to Nov 24
CA $222
CA $266 total
Nov 23 - Nov 24
includes taxes & fees
Grand Summit Resort, A Vail Resorts Property
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Nov 12 to Nov 13
CA $120
CA $132 total
Nov 12 - Nov 13
includes taxes & fees
6.4/10 (113 reviews)
"First room was awful and smelled very smokey despite being a non smoking room. Second room was much better."

Reviewed on Nov 3, 2026

Colonial Motel
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Nov 8 to Nov 9
CA $136
CA $147 total
Nov 8 - Nov 9
includes taxes & fees
Days Inn by Wyndham Keene NH
See all 1,754 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Brookline

Vermont RT 100 App-Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

CA $24
per traveller
80% of travellers recommend
Vermont RT 100 App-Guided Driving Audio Tour
Mindful Forest Escape: Rebalance, reflect and connect

Mindful Forest Escape: Rebalance, reflect and connect

CA $134
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 $793 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.

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