Brattleboro Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Brattleboro Vacation

Enjoy unforgettable adventures when you reserve a Brattleboro vacation package. Whether you're a history buff, foodie or just a traveler who loves to experience new places, there's something for everyone in this exciting city. A trip to Brattleboro is a great opportunity to do a bit of sightseeing. Check out popular attractions like The Stone Church, Brattleboro Common and Tasha Tudor Museum. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Brattleboro vacation plans into gear!

Top Brattleboro Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Chalet 239

Chalet 239

2 out of 5
Price was CA $1,000, price is now CA $959 per person
CA $959
per person
Aug 27 - Aug 30
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
9.4/10 Exceptional! (129 reviews)
Very clean and cute hotel. Will stay there again.

Reviewed on Jul 1, 2026

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was CA $1,458, price is now CA $1,177 per person
CA $1,177
per person
Aug 27 - Aug 30
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
10/10 Exceptional! (199 reviews)
Fantastic, beautiful property. We definitely want to visit again. Great for families.

Reviewed on Jul 4, 2026

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,214, price is now CA $1,028 per person
CA $1,028
per person
Aug 27 - Aug 30
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (907 reviews)
Love ithis hotel's industrial urban feel and proximity to shops and restaurants. Parking is close and included. The sheets and pillows are heaven. No kidding. I am not a Keurig coffee fan for a number of reasons: single use plastic and flavor among them and that is their lobby offering. But the staff are authentic, friendly, and just awesome. Interior room quietest option. This was a return stay.

Reviewed on Jul 4, 2026

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was CA $1,110, price is now CA $1,015 per person
CA $1,015
per person
Aug 27 - Aug 30
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (278 reviews)
The pool is unavailable until October! Doesn’t say that on Expedia

Reviewed on Jul 4, 2026

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was CA $1,242, price is now CA $1,186 per person
CA $1,186
per person
Sep 5 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
10/10 Exceptional! (114 reviews)
Holy and Kyle were awesome! Such wonderful breakfasts each day we were there, delicious! So close to everything we wanted to see. We look forward to coming back for our next Vermont getaway!

Reviewed on Jun 19, 2026

Ready to book your vacation to Brattleboro?

 

Choose your dates

Brattleboro Hotel Deals

Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jul 6 to Jul 7
CA $147
CA $161 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (919 reviews)
"Love ithis hotel's industrial urban feel and proximity to shops and restaurants. Parking is close and included. The sheets and pillows are heaven. No kidding. I am not a Keurig coffee fan for a number of reasons: single use plastic and flavor among them and that is their lobby offering. But the staff ..."

Reviewed on Jul 4, 2026

Latchis Hotel
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from Aug 2 to Aug 3
CA $109
CA $120 total
Aug 2 - Aug 3
includes taxes & fees
5.2/10 (11 reviews)
"Awful!"

Reviewed on Jul 3, 2026

Colonial Motel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jul 12 to Jul 13
CA $174
CA $191 total
Jul 12 - Jul 13
includes taxes & fees
8.2/10 Very good! (1,002 reviews)
"Really great spot for the price, very happy with our short stay."

Reviewed on Jul 4, 2026

Hampton Inn Brattleboro
See all 1,761 properties in Brattleboro
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

Stay near popular Brattleboro attractions

The Stone Church

8.6/10 (39 reviews)
After visiting The Stone Church, make a plan to see the other sights and activities in Brattleboro. While you're here, you can savor the top-notch restaurants.
See properties

What to do in Brattleboro

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 Brattleboro

Frequently asked questions

How much does a Brattleboro vacation package cost?
Offering excellent value package deals from CA $959 on Expedia, you'll be thrilled with how little a vacation to Brattleboro costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Brattleboro?
If you're looking to snag a cheap Brattleboro vacation package, consider visiting in January, April and November. You'll generally find better rates on airfares and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Brattleboro?
For a Brattleboro vacation, a handful of days will be enough to tour all the highlights. Be sure to visit Latchis Theatre — it's one of the major attractions in this destination. If you want more adventure, think about basing yourself here and going on some trips from Brattleboro.
Is it worth booking a vacation package to Brattleboro?
Brattleboro is a good vacation destination with attractions like The Stone Church among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Brattleboro vacation promises a good time for everyone.
How to find the best Brattleboro package deals?
Finding a cheap Brattleboro package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Brattleboro package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Brattleboro vacation as a package?
You can enjoy significant savings on your next Brattleboro retreat by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
How to plan a trip to Brattleboro?

  1. Pick your dates: The things you'd like to do in Brattleboro and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: On top of the cost of your accommodations, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may come up during your trip to Brattleboro.
  3. Decide your trip length: Think about how long you want to spend exploring Brattleboro. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Brattleboro 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.