Brattleboro Vacations from $784
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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.
Vikings Villages Resort
$1,097
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
10/10 Exceptional! (240 reviews)
Love our stay in Vikings. Staff was amazing and very attentive and helpful. The cabins were beautiful, clean and had everything we needed. Very recommended. Hope to go back in the future.
Reviewed on Oct 13, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
$2,619
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
8.6/10 Excellent! (908 reviews)
I can’t say enough about how enjoyable it was! Will be back!
Reviewed on Oct 13, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
$6,910
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
7.8/10 Good! (28 reviews)
The unit was very clean. However, there was a distinct musty/moldy smell throughout the unit as if had been sitting for quite sometime. We did bring a scented candle to help and was able to use the fireplace which also helped with the smell. All and all, for an older unit, the stay was not bad, the neighbors were great and it was peaceful aling with a beautiful view. We would like to stay there again.
Reviewed on Oct 12, 2026
Lincoln Inn & Gallery
$1,097
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (98 reviews)
Lincoln Inn looks charming, especially at the height of leaf-peeping season. However, there are three things that are subpar. No breakfast. No television (which isn't a problem unless there is an important sporting event you are following). Weak and volatile Wi-Fi. If none of those things is important to you, then Lincoln Inn is perfectly fine. Otherwise, you will leave frustrated.
Reviewed on Oct 12, 2026
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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 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.
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 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.
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.
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.
River Gallery School
Explore the campus of River Gallery School during your stay in Brattleboro. While you're here, you can savor the top-notch restaurants.
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
$99 nightly
$109 total
Nov 1 - Nov 2
Total with taxes and fees
6.2/10 (89 reviews)
"Lovely visit. Friendly staff."
Reviewed on Oct 12, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$140 nightly
$154 total
Nov 2 - Nov 3
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
1186 Putney Road Brattleboro VT
Fully refundable
$111 nightly
$122 total
Nov 8 - Nov 9
Total with taxes and fees
8.6/10 Excellent! (882 reviews)
"Clean room, staff were polite and friendly"
Reviewed on Oct 13, 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 $784 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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- Visit Brattleboro
- The Stone Church
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- Mount Snow
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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.