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Brattleboro Vacation Packages

A river with a bridge, a town, and surrounding hills.

Brattleboro Flight + Hotel Packages

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

Jackson Gore Village, A Vail Resorts Property

$550

per person

Oct 30 - Nov 1

found 17 hours ago

Roundtrip non-stop flight included

San Diego (SAN) to Springfield (VSF)

Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.

Beautiful resort. I love it!

Reviewed on Aug 4, 2026

Latchis Hotel

$621

per person

Sep 5 - Sep 8

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Springfield (VSF)

Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.

Main Street Brattleboro so great, near Restaurants and entertainment. We saw a film downstairs, LPs and are Record player in Rooms!

Reviewed on Aug 3, 2026

Deer Brook Inn

$791

per person

Oct 30 - Nov 1

found 17 hours ago

Roundtrip non-stop flight included

San Diego (SAN) to Springfield (VSF)

Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and climate control. Popular attractions Ottaquechee River and Union Arena Community Center are located nearby.

Okemo Mountain Lodging by Vail Resorts

$666

per person

Oct 30 - Nov 1

found 17 hours ago

Roundtrip non-stop flight included

San Diego (SAN) to Springfield (VSF)

Stay at this vacation home in Ludlow. Enjoy free parking, laundry facilities, and cable TV channels. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.

Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.

Reviewed on Jun 26, 2025

Stay At Jimmy's

$680

per person

Oct 30 - Nov 1

found 17 hours ago

Roundtrip non-stop flight included

San Diego (SAN) to Springfield (VSF)

Stay at this B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Quechee Gorge Bridge and Billings Park and Trail are located nearby.

The room and amenities exceeded our expectations. It was the best B & B we ever stayed in. The location was near shopping, restaurants and hiking trails. I highly recommend. You will not be disappointed.

Reviewed on Jul 29, 2026

Winterplace at Okemo, A Vail Resorts Property

$639

per person

Oct 30 - Nov 1

found 17 hours ago

Roundtrip non-stop flight included

San Diego (SAN) to Springfield (VSF)

Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.

Enjoyable and beautiful place. Ann

Reviewed on Jul 20, 2026

Chalet 239

$574

per person

Sep 5 - Sep 8

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Springfield (VSF)

Stay at this motel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.

The room was small. But very new, modern and clean. I’d stay again.

Reviewed on Aug 1, 2026

Solitude Village at Okemo by Vail Resorts

$598

per person

Oct 30 - Nov 1

found 17 hours ago

Roundtrip non-stop flight included

San Diego (SAN) to Springfield (VSF)

Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.