Brattleboro Vacations from $553

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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.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $675, price is now $553 per person
$553
per person
Jan 21 - Jan 23
found 24 hours ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (242 reviews)
Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability

Reviewed on Oct 18, 2025

Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $10,811, price is now $8,597 per person
$8,597
per person
Jan 29 - Feb 2
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8/10 Very Good! (31 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.

Reviewed on Oct 8, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,566, price is now $1,276 per person
$1,276
per person
Jan 29 - Feb 2
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good.

Reviewed on Nov 30, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $775, price is now $643 per person
$643
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
Wonderful place to stay!

Reviewed on Dec 3, 2025

Windham Hill Inn

Windham Hill Inn

4 out of 5
Price was $721, price is now $621 per person
$621
per person
Jan 15 - Jan 19
found 3 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
8.6/10 Excellent! (37 reviews)
The Inn is situated near the top of a mountain and surrounded by other hilltops. There are trails that help you to reconnect with nature. Our room was lovely and comfortable. There is a attention to detail in the decor of this establishment which is both delightful and humorous.

Reviewed on Jul 11, 2025

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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

Vermont Marketplace

You can browse for the perfect souvenirs at Vermont Marketplace during your visit to Brattleboro. While you're here, you can savor the top-notch restaurants.

Vermont Marketplace

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

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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $158 total per night from Dec 10 to Dec 11
$158 total
Dec 10 - Dec 11
Total with taxes and fees
8.2/10 Very Good! (923 reviews)
Everything was very nice. I was checked in at the desk by "Jolene" who was cordial, friendly, and welcoming. The room was very clean and it was very quiet. The breakfast in the morning was excellent as was the coffee station. I do miss the little snack bag at the front desk where we could grab 'n ...

Reviewed on Nov 20, 2025

Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $127 total per night from Dec 18 to Dec 19
$127 total
Dec 18 - Dec 19
Total with taxes and fees
8.4/10 Very Good! (736 reviews)
Staff was friendly and pool was nice

Reviewed on Dec 1, 2025

Comfort Inn & Suites Brattleboro I-91
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $87 total per night from Dec 6 to Dec 7
$87 total
Dec 6 - Dec 7
Total with taxes and fees
7.6/10 Good! (1,007 reviews)
Room very nice, comfortable clean

Reviewed on Nov 29, 2025

The Covered Bridge Inn
See all 1,703 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 $553 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.

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.