Search Deals onBrattleboro Vacation Packages
Brattleboro Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
Price was $751, price is now $699 per person
$699
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.
Friendly owners and the property was amazing Beautiful garden, even in the fall Breakfast was delicious
Reviewed on Sep 25, 2026
The Shire Woodstock
Price was $1,653, price is now $1,380 per person
$1,380
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Great views
Reviewed on Sep 25, 2026
Jackson Gore Village, A Vail Resorts Property
Price was $933, price is now $859 per person
$859
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Nice hot tubs
Reviewed on Sep 25, 2026
Winterplace at Okemo, A Vail Resorts Property
Price was $852, price is now $793 per person
$793
per person
Oct 28 - Oct 31
found 1 hour ago
Roundtrip non-stop flight included
Orlando (MCO) 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
Solitude Village at Okemo by Vail Resorts
Price was $1,005, price is now $942 per person
$942
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Okemo Mountain Lodging by Vail Resorts
Price was $938, price is now $884 per person
$884
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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
Mountain Lodge at Okemo, A Vail Resorts Property
Price was $910, price is now $858 per person
$858
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall
Reviewed on Jul 19, 2026
Lincoln Inn & Gallery
Price was $1,095, price is now $1,034 per person
$1,034
per person
Oct 28 - Oct 31
found 4 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this guesthouse in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.
Beautiful property! Our room was clean and beautiful! Wasn’t crazy about the room overlooking the road and not having dinner or bfast at the resort. Staff was very nice and super accommodating!!!! The hot chocolate bar is a major plus
Reviewed on Sep 23, 2026
Brattleboro Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
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