Brattleboro Vacations from $1,035
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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!
The Latest Brattleboro vacation packages
Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock
$1,043
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (978 reviews)
We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along.
The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the
view although this wasn't a game changer.
Reviewed on Aug 27, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
$1,078
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on Jun 26, 2025
Mountain Lodge at Okemo, A Vail Resorts Property
Clock Tower Base Area
$1,045
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8/10 Very Good! (225 reviews)
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall
Reviewed on Jul 19, 2026
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See all available trips from Columbus to Brattleboro
View all tripsStay near popular Brattleboro attractions
The Stone Church
8.6/10 (39 reviews)
This Gothic Revival church turned music venue captivates with stained glass windows and a stage built from pews. Experience intimate performances with exceptional acoustics in this distinctive Vermont listening room.
Vermont Marketplace
10.0/10 (1 review)
Vermont Marketplace showcases local artisans and Vermont specialty products in a charming country store setting. Browse handcrafted items and gourmet foods, then unwind at the cozy tavern with regional craft beers.
Brattleboro Common
8.6/10 (43 reviews)
This historic town green features a charming bandstand and solemn memorials honoring local veterans. Take a peaceful break beneath mature trees while experiencing a slice of authentic Vermont community life.
Latchis Theatre
9.0/10 (12 reviews)
This historic Art Deco venue features Greek-inspired murals and a zodiac ceiling in its grand theatre. Experience mainstream films and art house cinema while surrounded by the Latchis family's cultural legacy.
Hogback Mountain Conservation Area
Hogback Mountain offers a breathtaking 100-mile panoramic view spanning three New England states. Hike through its 600-acre preserve to spot native wildlife from black bears to neotropical warblers.
Brattleboro Farmers' Market
8.8/10 (75 reviews)
Southern Vermont's premier market brings together 50+ vendors selling fresh produce, international cuisine, and artisan crafts. Enjoy live music while sampling local delights at picnic tables beside a babbling brook.
New England Center for Circus Arts
10.0/10 (1 review)
At NECCA, America's premier circus training school, learn to soar on trapeze or master aerial silks. Take a beginner workshop or attend a student showcase in their custom-designed Trapezium facility.
Scott Farm Orchard
This historic orchard cultivates over 130 heirloom apple varieties using ecological practices since 1791. Wander through grounds, sample rare fruits at the Farm Market, and enjoy seasonal events like Heirloom Apple Days.
What to do in Brattleboro
Vermont RT 100 App-Guided Driving Audio Tour
$17
per traveler
Mindful Forest Escape: Rebalance, reflect and connect
$95
per adult
Brattleboro Hotel Deals
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$83 nightly
$91 total
Sep 9 - Sep 10
Total with taxes and fees
6.8/10 (46 reviews)
"It was dirty. The sink, bathroom, tub, floors. All dead bugs all over. TV was great. But a very musty smell in room. My sheets were not dry when we went to bed."
Reviewed on Aug 26, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$152 nightly
$167 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (969 reviews)
"Great stay! Very clean."
Reviewed on Aug 28, 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$116 nightly
$127 total
Sep 9 - Sep 10
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
"Very clean. Good full breakfast."
Reviewed on Aug 26, 2026
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.
Find the Best Brattleboro Vacation Packages
Brattleboro Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 7,400 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Brattleboro Museum & Art Center, Brattleboro Bowl and Fort Dummer State Park |
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Frequently asked questions
How much does a Brattleboro vacation package cost?
Offering great value package deals from $1,035 on Expedia, you'll be thrilled with how little a vacation to Brattleboro costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Brattleboro?
March, June and November are the best times to look for cheap Brattleboro vacation packages. Opting to travel in quieter periods means you can typically find reduced prices on flights and accommodations.
How many days is enough for Brattleboro?
For your Brattleboro vacation, a handful of days will be enough to tour the best spots. Be sure to visit Fort Dummer State Park — it's one of the leading sights in this destination. If you're looking for more adventure, think about basing yourself here and heading off on some day 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 entertained. Whether you're heading away with the family or getting away with friends, a Brattleboro vacation promises fun for everyone.
How to find the best Brattleboro package deals?
Use Expedia's handy filters to help you find some tempting Brattleboro package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Brattleboro package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Brattleboro vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging accommodations and flights separately. Better still, you can customize your Brattleboro getaway 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 Brattleboro?
If you've got your Brattleboro travel dates confirmed, book as early as you can to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Brattleboro?
- Pick your dates: The things you'd like to do in Brattleboro and your favorite season will help you decide when to travel.
- Work out your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your accommodations will probably be the largest expense during your trip to Brattleboro.
- Organize your Brattleboro escape with our trip planning tool: Search for and book accommodations and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Brattleboro together.
- Work out your trip length: Think about how much time you want to spend exploring Brattleboro. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Combine your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Brattleboro vacation package for you.
- Book any activities or excursions: Here's the fun part — organizing everything you want to do and see. Browse some of the incredible things to do in Brattleboro and reserve your tickets in advance to save time (and maybe some spending money too!).
Does Expedia offer Book Now, Pay Later Brattleboro vacation packages?
If you're anything like us, you love traveling but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Brattleboro break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
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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.
