Search Deals onStockbridge Vacation Packages
Stockbridge Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
Price was $852, price is now $764 per person
$764
per person
Sep 10 - Sep 14
found 12 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 Mills Riverside Park and Waters Memorial Library are located nearby.
Holy and Kyle were awesome! Such wonderful breakfasts each day we were there, delicious! So close to everything we wanted to see. We look forward to coming back for our next Vermont getaway!
Reviewed on Jun 19, 2026
The Shire Woodstock
Price was $1,782, price is now $1,451 per person
$1,451
per person
Aug 20 - Aug 24
found 7 hours 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 Quechee Gorge Bridge and Billings Park and Trail are located nearby.
Very nice property. Would be great to have coffee in the rooms. Also very limited hot water. Ran out a few times even after a quick shower.
Reviewed on Jul 12, 2026
Greenbrier Inn
Price was $954, price is now $835 per person
$835
per person
Aug 20 - Aug 24
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington Resort and Fire Tower are located nearby.
The hotel was very nice, quaint and clean. It is in a great location just prior to the entry of the access road. Large room. Small hotel with only about 20 rooms. Breakfast included. I would recommend a stay.
Reviewed on Jul 16, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was $969, price is now $856 per person
$856
per person
Aug 20 - Aug 24
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Lebanon (LEB)
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 Mount Ascutney and Mt Ascutney State Park are located nearby.
Nice staff, fun activities
Reviewed on Jul 12, 2026
The Mountain Inn at Killington
Price was $922, price is now $835 per person
$835
per person
Aug 20 - Aug 24
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Good location. Small pool and no chairs around pool
Reviewed on Jul 16, 2026
Jackson Gore Village, A Vail Resorts Property
Price was $978, price is now $888 per person
$888
per person
Aug 20 - Aug 24
found 7 hours 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.
Great family friendly location!
Reviewed on Jul 11, 2026
Bentley House Bed and Breakfast
Price was $898, price is now $820 per person
$820
per person
Aug 20 - Aug 24
found 7 hours ago
Roundtrip non-stop 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.
Great place, friendly owners. I will be coming back.
Reviewed on Jul 11, 2026
Winterplace at Okemo, A Vail Resorts Property
Price was $1,149, price is now $1,051 per person
$1,051
per person
Aug 20 - Aug 24
found 7 hours 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.
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty
Reviewed on Dec 1, 2025
Stockbridge Vacation Packages 3-4 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.
Tue, Oct 6 - Tue, Oct 13
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$330 Roundtrip, found 22 hours ago
$330
Roundtrip
found 22 hours ago
Tue, Oct 6 - Wed, Oct 14
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$340 Roundtrip, found 22 hours ago
$340
Roundtrip
found 22 hours ago
Sat, Oct 10 - Mon, Oct 12
IAD
Washington Dulles Intl.
LEB
Lebanon Municipal
$412 Roundtrip, found 22 hours ago
$412
Roundtrip
found 22 hours ago
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 17 hours ago
$513
Roundtrip
found 17 hours ago
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