Brattleboro Vacations from $402

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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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Springfield (VSF)
8.8/10 Excellent! (472 reviews)
I had an excellent stay at the Mountaineer Inn. The Inn was very clean, quiet, and peaceful. I just wish the pool was available for use. I’m confident the I will stay at the Mountaineer Inn again in the future.

Reviewed on Jun 30, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Springfield (VSF)
8.8/10 Excellent! (762 reviews)
Great location!! Very accommodating and clean.

Reviewed on Jun 28, 2025

Latchis Hotel

Latchis Hotel

2.5 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
8.4/10 Very Good! (745 reviews)
This property, an old deco building and is in a great location for exploring downtown Brattleboro. The rooms themselves vary from pretty nice to quite dark and unwelcoming, the latter being those that face an air shaft instead of a proper exterior view. The staff are incredibly helpful and were able to get us upgraded to an outside room when we raised concerns about being in an air shaft room. The cleaning staff is extremely friendly and this is a pet friendly hotel and they were all very warm to our dog.

Reviewed on Jun 30, 2025

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
West Woodstock
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Springfield (VSF)
9.6/10 Exceptional! (10 reviews)
Nice view with spacious grounds. I see potential for lovely garden with a little help

Reviewed on Jun 25, 2025

Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Springfield (VSF)
8.8/10 Excellent! (23 reviews)
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Discover the most popular places to visit in Brattleboro

The Stone Church

4.5/5(9 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.

The Stone Church

Brattleboro Common

Explore the great outdoors at Brattleboro Common, a lovely green space in Brattleboro. Experience the area's entertainment venues and art scene.

Brattleboro Common

Brattleboro Farmers' Market

4/5(31 reviews)

You can enjoy retail therapy at Brattleboro Farmers' Market during your visit to West Brattleboro. Discover the area's entertainment venues, or seek out its ski slopes.

Brattleboro Farmers' Market

What to do in Brattleboro

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

$17
per traveler
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Brattleboro

Brattleboro Hotel Deals

Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $120 total per night from Jul 6 to Jul 7
$120 total
Jul 6 - Jul 7
Total includes taxes and fees
6.6/10 (1,002 reviews)
"We like the room. Nice and spacious. Er"

Reviewed on Jul 2, 2025

Colonial Motel And Spa
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $139 total per night from Jul 13 to Jul 14
$139 total
Jul 13 - Jul 14
Total includes taxes and fees
8/10 Very Good! (840 reviews)
"Great for the price"

Reviewed on Jun 28, 2025

Hampton Inn Brattleboro
Latchis Hotel
Latchis Hotel
2.5 out of 5
50 Main Street, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $144 total per night from Jul 14 to Jul 15
$144 total
Jul 14 - Jul 15
Total includes taxes and fees
8.4/10 Very Good! (751 reviews)
"This property, an old deco building and is in a great location for exploring downtown Brattleboro. The rooms themselves vary from pretty nice to quite dark and unwelcoming, the latter being those that face an air shaft instead of a proper exterior view. The staff are incredibly helpful and were able ..."

Reviewed on Jun 30, 2025

Latchis Hotel
See all 1,676 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.

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 $402 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?

  1. Pick your dates: The things you'd like to do in Brattleboro and your favorite season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.
  5. Combine your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Brattleboro vacation package for you.
  6. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.