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Stockbridge Vacation Packages

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Stockbridge Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,022, price is now $820 per person
$820
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Lebanon (LEB)
Stay at this 3-star resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,135, price is now $886 per person
$886
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 3-star 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.
Hanover Inn Dartmouth

Hanover Inn Dartmouth

4 out of 5
Price was $1,134, price is now $896 per person
$896
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Lebanon (LEB)
Stay at this 4-star luxury hotel in Hanover. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Hopkins Center for the Arts and Left Bank Books are located nearby.
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Price was $1,586, price is now $1,260 per person
$1,260
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Price was $1,319, price is now $1,072 per person
$1,072
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Price was $1,301, price is now $1,057 per person
$1,057
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Price was $1,252, price is now $1,025 per person
$1,025
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 3.5-star vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Price was $1,180, price is now $974 per person
$974
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 3-star ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.

Stockbridge Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $649, price is now $574 per person
$574
per person
Dec 4 - Dec 7
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,085, price is now $903 per person
$903
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $905, price is now $775 per person
$775
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Lebanon (LEB)
Brook Road Cabin

Brook Road Cabin

3.5 out of 5
Price was $673, price is now $599 per person
$599
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Lebanon (LEB)

Stockbridge Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,022, price is now $820 per person
$820
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Lebanon (LEB)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,135, price is now $886 per person
$886
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Hanover Inn Dartmouth

Hanover Inn Dartmouth

4 out of 5
Price was $1,134, price is now $896 per person
$896
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Lebanon (LEB)
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was $1,586, price is now $1,260 per person
$1,260
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Tue, Oct 7 - Tue, Oct 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$156 Roundtrip, found 1 day ago
$156
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Oct 7 from Logan Intl. to Lebanon Municipal, returning Tue, Oct 7, priced at $156 found 1 day ago
JetBlue Airways
Sat, Oct 18 - Tue, Oct 28
RDU
Raleigh - Durham Intl.
LEB
Lebanon Municipal
$345 Roundtrip, found 1 day ago
$345
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Oct 18 from Raleigh - Durham Intl. to Lebanon Municipal, returning Tue, Oct 28, priced at $345 found 1 day ago
JetBlue Airways
Mon, Oct 20 - Fri, Oct 24
RDU
Raleigh - Durham Intl.
LEB
Lebanon Municipal
$351 Roundtrip, found 4 days ago
$351
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Oct 20 from Raleigh - Durham Intl. to Lebanon Municipal, returning Fri, Oct 24, priced at $351 found 4 days ago
Delta
Tue, Oct 21 - Tue, Oct 28
SAN
San Diego Intl.
LEB
Lebanon Municipal
$448 Roundtrip, found 1 day ago
$448
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 21 from San Diego Intl. to Lebanon Municipal, returning Tue, Oct 28, priced at $448 found 1 day ago