Brattleboro Vacations from $645

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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 Vesper

The Vesper

3 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
9.4/10 Exceptional! (27 reviews)
Charming quaint place with artistic decor. Care was taken with the breakfast - delicious, homemade and wonderful presentation. It felt very homey. Prompt response to my texts; excellent communication. Welcoming and friendly. I would definitely stay here again and recommend the Vesper highly.

Reviewed on Jul 17, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Oct 20 - Oct 24
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (796 reviews)
I liked the outdoor seating and the location along with the view. The comfort of the beds doesn’t match the price you have to pay and our room had ants in it.

Reviewed on Aug 17, 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
per person
Oct 5 - Oct 8
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
9.6/10 Exceptional! (54 reviews)
This is such a charming, historic New England bed and breakfast. The quintessential Vermont experience right in the heart of the quaint village of West Dover. The Innkeeper knows all the people & places around. Homemade breakfast options are delicious, I had the local blueerry waffles. The Blueberry Festival parade passed right in front of the inn. I drank the Inn's coffee in the morning outside on their lawn, on one of the oversized stone seats around the firepit. There are books on the shelves and games in the living room. The Inn is in a perfect location, walking distance - with sidewalks - to multiple restaurants. And just 10 minutes to the town of Wilmington and the GORGEOUS water at Harriman Reservoir or Lake Raponda. There's 2 golf courses a few minutes away. And 2 ski mountains too! This place is super quiet, but close to whatever you might need. The Inn is filled with cozy furnishings, antiques, fireplaces, etc. Lovely lovely, so New England, so Vermont.

Reviewed on Aug 8, 2025

Mountaineer Inn

Mountaineer Inn

2 out of 5
per person
Oct 5 - Oct 8
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (495 reviews)
It was a beautiful location...so quiet and peaceful The rooms to sit and enjoy were wonderful

Reviewed on Aug 9, 2025

Chalet 239

Chalet 239

2 out of 5
per person
Oct 5 - Oct 8
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
9.4/10 Exceptional! (70 reviews)
Teh staff were friendly and helpful. Immediately upon booking I received a text message from the staff letting me know someone was there to help with any questions. checking in was easy and the hotel was very clean. The room, beds and bathroom were all clean and well kept. The free breakfast was a plus.

Reviewed on Aug 12, 2025

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Discover the most popular places to visit in Brattleboro

The Stone Church

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

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
$140 nightly
The price is $154 total per night from Aug 19 to Aug 20
$154 total
Aug 19 - Aug 20
Total includes taxes and fees
6.6/10 (1,006 reviews)
"Staff was helpful. Quiet area"

Reviewed on Aug 17, 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
$122 nightly
The price is $135 total per night from Sep 2 to Sep 3
$135 total
Sep 2 - Sep 3
Total includes taxes and fees
8/10 Very Good! (866 reviews)
"Great beach and nice rooms Breakfast can improve and pool is small"

Reviewed on Aug 17, 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
$140 nightly
The price is $153 total per night from Sep 7 to Sep 8
$153 total
Sep 7 - Sep 8
Total includes taxes and fees
8.4/10 Very Good! (773 reviews)
"I loved everything about this place. I will be back!"

Reviewed on Aug 14, 2025

Latchis Hotel
See all 1,659 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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Frequently asked questions

How much does a Brattleboro vacation package cost?
Offering great value package deals from $645 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.