Search Deals onStockbridge Vacation Packages
Stockbridge Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
Price was $631, price is now $501 per person
$501
per person
Dec 17 - Dec 21
found 15 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Lincoln Inn & Gallery
Price was $1,686, price is now $1,068 per person
$1,068
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
The hotel was amazing and the staff was so kind. Luke was working the front desk and made sure we had everything we needed. The hotel and property are beautiful. We really enjoyed our time and can't wait to come back!
Reviewed on Nov 8, 2026
Mountain Green Resort
Price was $4,146, price is now $3,306 per person
$3,306
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Book a stay at this business-friendly apartment in Killington. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Killington Resort and Black Dog Sports are located nearby.
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was $1,204, price is now $961 per person
$961
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions T-Bar and Rope Tow are located nearby.
We were so happy with everything
Clean linens
Well stocked kitchen
Great grounds
Helpful staff
One minor issue--heat in halls too high, like uncomfortably warm
We had windows open at times in November
Reviewed on Nov 9, 2026
The Suites at Killington Center
Price was $3,601, price is now $2,890 per person
$2,890
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
The Shire Woodstock
Price was $1,940, price is now $1,646 per person
$1,646
per person
Dec 23 - Dec 27
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Quechee Gorge Bridge and Billings Park and Trail are located nearby.
Perfect stay in a beautiful town. Can't wait to come back.
Reviewed on Nov 11, 2026
My Place Hotel-Randolph VT
Price was $834, price is now $713 per person
$713
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.
1846 Inn and Tavern
Price was $935, price is now $810 per person
$810
per person
Dec 17 - Dec 21
found 15 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
The Inn also has an adjacent nice food tavern and music this weekend. Friendly host - embodied the helpful spirit of old inns. Helped with allowing a late dinner due to late arrival. Adjusted the heat for us and allowed us to set a bit extra in their library.
Very welcoming. A ++ for hospitality and making us welcome!
Reviewed on Oct 12, 2026
Stockbridge Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Stockbridge Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$555 Roundtrip, found 4 days ago
$555
Roundtrip
found 4 days ago
Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$575 Roundtrip, found 4 days ago
$575
Roundtrip
found 4 days ago
Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$581 Roundtrip, found 4 days ago
$581
Roundtrip
found 4 days ago
Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$594 Roundtrip, found 3 days ago
$594
Roundtrip
found 3 days ago
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