West Brattleboro Vacations from $585

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Your West Brattleboro Vacation

With one of our vacation packages to West Brattleboro, you'll have countless opportunities for fun and excitement. There's a lot to enjoy, including its rich history and spectacular views. The Stone Church, Brattleboro Common and Tasha Tudor Museum are just some of the sights worth visiting during your trip to West Brattleboro. A couple of clicks is all it takes to build the ultimate West Brattleboro vacation on Expedia.

The Latest West Brattleboro vacation packages

Price found within the past 48 hours. Click for updated prices.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $652, price is now $585 per person
$585
per person
Oct 17 - Oct 19
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
8.8/10 Excellent! (503 reviews)
Easy in and out. All transactions with this property are handled online; there was no person-to-person interaction while on the site. The rooms and bathrooms were clean, and the beds were comfortable. We'd consider this again in the future.

Reviewed on Aug 23, 2025

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $791, price is now $667 per person
$667
per person
Oct 20 - Oct 24
found 15 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Springfield (VSF)
8.4/10 Very Good! (780 reviews)
Lovely réception but the hôtel is dated. 8.5/10

Reviewed on Sep 3, 2025

Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was $962, price is now $839 per person
$839
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.8/10 Excellent! (23 reviews)
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Price was $933, price is now $816 per person
$816
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8/10 Very Good! (26 reviews)
Very friendly costumer service, we arrived late and we're greated with kindness.

Reviewed on Sep 16, 2024

Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
Price was $760, price is now $682 per person
$682
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8/10 Very Good! (208 reviews)
Loved the location for this ski in ski out. Nice to look out the balcony and be right in the middle of the action. The sofa bed was uncomfortable with springs popping up all over. The back door didn't lock and the window handle was broken . There was a light bulb that was out and not all the outlets worked. The tv situation was a nightmare with one tv all snowy and the other one whose remote was missing the select button and could not choose a channel. The location was great but would not choose this room again .

Reviewed on Feb 19, 2025

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Discover the most popular places to visit in West 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 West 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 West Brattleboro

West Brattleboro Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $136 total per night from Sep 14 to Sep 15
$136 total
Sep 14 - Sep 15
Total with taxes and fees
Keene Elm City Hotel, Ascend Hotel Collection
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 Sep 14 to Sep 15
$139 total
Sep 14 - Sep 15
Total with taxes and fees
Hampton Inn Brattleboro
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $173 total per night from Sep 7 to Sep 8
$173 total
Sep 7 - Sep 8
Total with taxes and fees
Best Western Plus Keene Hotel
See all 1,158 properties in West 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 West Brattleboro vacation package cost?
Offering great value package deals from $585 on Expedia, you'll be thrilled with how little a vacation to West Brattleboro costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to West Brattleboro?
March, June and November are great times to look for cheap West Brattleboro vacation packages. Choosing to travel in quieter months means you'll typically find reduced prices on flights and accommodations.
How many days is enough for West Brattleboro?
Typically, a handful of days is enough to visit the major attractions during your West Brattleboro vacation. But if you prefer to have more time to chill out or take day trips, think about extending your itinerary.
How to find the best West Brattleboro package deals?
Start your search for a West Brattleboro package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal West Brattleboro package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your West Brattleboro adventure off to a flying start.
Is it cheaper to book a West Brattleboro vacation as a package?
You can enjoy significant savings on your next West Brattleboro retreat by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to West Brattleboro?
If you've got your West Brattleboro vacation dates locked in, book as soon as you can to score some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later West Brattleboro vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your West Brattleboro vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.