Brattleboro Vacation Packages

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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.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was CA $1,141, price is now CA $1,050 per person
CA $1,050
per person
Aug 14 - Aug 17
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (284 reviews)
We were very disappointed upon arrival to hear that the pool was closed for the summer. It was 4th of July weekend and we were traveling with grandkids. We would not have booked there if we had known.

Reviewed on Jul 10, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $2,961, price is now CA $2,067 per person
CA $2,067
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Springfield (VSF)
8.8/10 Excellent! (954 reviews)
Absolutely beautiful setting! The room was better than expected-- spacious, clean and gorgeously decorated. The location was also great-- everything was walkable. Highly recommend.

Reviewed on Jul 5, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was CA $1,442, price is now CA $1,063 per person
CA $1,063
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (862 reviews)
great location but dated

Reviewed on Jul 10, 2026

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was CA $1,756, price is now CA $1,515 per person
CA $1,515
per person
Aug 15 - Aug 21
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,419, price is now CA $1,246 per person
CA $1,246
per person
Aug 14 - Aug 17
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (915 reviews)
We loved our stay at the Latchis! A gem, with great staff and unique character! Can't wait to return!

Reviewed on Jul 10, 2026

Ready to book your vacation to Brattleboro?

 

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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 $172 per night from Jul 12 to Jul 13
CA $172
CA $190 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (926 reviews)
"We loved our stay at the Latchis! A gem, with great staff and unique character! Can't wait to return!"

Reviewed on Jul 10, 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 $108 per night from Aug 2 to Aug 3
CA $108
CA $119 total
Aug 2 - Aug 3
includes taxes & fees
5.4/10 (13 reviews)
"The bed was hard to sleep on, the outdoor pool was filled with dirt, the indoor pool/spa/massage area is dilapidated, and the continental breakfast offered the bare minimum. When using the shower, switching from tub to shower was a task in itself while the water pressure was weak"

Reviewed on Jul 6, 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 $194 per night from Jul 19 to Jul 20
CA $194
CA $213 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (1,007 reviews)
"staff was nice room was clean bed was comfortable, pool was nice, breakfast was good"

Reviewed on Jul 10, 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.
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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 $135
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 $1,050 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.