Search Deals onStockbridge Vacation Packages
Stockbridge Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

My Place Hotel-Randolph VT
Price was $767, price is now $595 per person
$595
per person
Jan 10 - Jan 17
found 9 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.

Vikings Villages Resort
Price was $1,020, price is now $763 per person
$763
per person
Dec 30 - Jan 3
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Keets Brook Road Conservation Area are located nearby.
Viking Village is perfect in every way! If you're looking for a relaxed retreat, trails, nature, and delightfully detailed cabins and buildings, this is your dream stay. As you drive up toward the gates a sense of anticipation builds until the stockade fence and gate comes into view. It truly looks like you've traveled back in time once you arrive. Every cabin is slightly different. A raised walkway was thoughtfully built along the fronts of the cabins so you can avoid any snow or dirt as you come and go. Check-in is quick and Christina also gave us recommendations of nearby places to see or dine. The kitchenette does have what you'd need to cook and eat with for 4 people. Cabins are immaculate. Beds were comfortable. We made it a point to go out for the morning and evening feeding of the sheep. They may have been my favorite part of the stay! especially the lambs! We stayed 2 nights and enjoyed chatting with other guests around the firepit in the evening. (Their kids absolutely LOVED this place.) My husband and I are in our sixties and found the trails a little challenging! Quite hilly, but well marked. A heartfelt thank you to the folks running the Village. You were gracious hosts and made this someplace that we want to return to again! (Easier to get to than Iceland!)
Reviewed on Nov 7, 2026

Latchis Hotel
Price was $716, price is now $604 per person
$604
per person
Dec 30 - Jan 3
found 11 hours ago
Roundtrip 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.

The Shire Woodstock
Price was $1,394, price is now $1,187 per person
$1,187
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) 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.

Mountain Green Resort
Price was $1,874, price is now $1,604 per person
$1,604
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) 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

Sinclair Inn Bed and Breakfast
Price was $1,103, price is now $951 per person
$951
per person
Jan 10 - Jan 17
found 9 hours 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.

The Suites at Killington Center
Price was $1,506, price is now $1,319 per person
$1,319
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) 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.

Bentley House Bed and Breakfast
Price was $682, price is now $600 per person
$600
per person
Dec 30 - Jan 3
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park are located nearby.
Clean, comfortable, convenient. We couldn't stay for breakfast.
Reviewed on Nov 8, 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
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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 1 day ago
$555
Roundtrip
found 1 day ago

Thu, Nov 19 - Sat, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$565 Roundtrip, found 3 days ago
$565
Roundtrip
found 3 days ago

Thu, Nov 19 - Sat, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$570 Roundtrip, found 3 days ago
$570
Roundtrip
found 3 days ago

Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$575 Roundtrip, found 1 day ago
$575
Roundtrip
found 1 day ago
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