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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.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $584, price is now $521 per person
$521
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.
proche des pentes

Reviewed on Aug 6, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,062, price is now $786 per person
$786
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.
Giid hotel with several fire pits to sit by the river

Reviewed on Aug 6, 2026

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $737, price is now $631 per person
$631
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Lebanon (LEB)
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.
I feel at home here

Reviewed on Aug 6, 2026

Brook Road Inn

Brook Road Inn

3 out of 5
Price was $702, price is now $605 per person
$605
per person
Oct 10 - Oct 16
found 13 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Lebanon (LEB)
Stay at this guesthouse in Goshen. Enjoy free WiFi, free parking, and air conditioning. Popular attractions Lake Sunapee and Gunnison Lake are located nearby.
The room was very clean and our bathroom was amazing! You cannot have food in your room and there isn’t a tv or anything in there. I didn’t see any staff at the place. It wasn’t explained to me how to get into the place very well at all so it took us a few minutes to figure it out and we felt kind of foolish. It was fine if you just wanted a place to sleep for the night but we probably wouldn’t go back.

Reviewed on Jun 15, 2026

Deer Brook Inn

Deer Brook Inn

3 out of 5
Price was $900, price is now $791 per person
$791
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and climate control. Popular attractions Ottaquechee River and Union Arena Community Center are located nearby.

The Inn at Weathersfield

The Inn at Weathersfield

4 out of 5
Price was $700, price is now $617 per person
$617
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Lebanon (LEB)
Stay at this inn in Perkinsville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions North Springfield Lake Recreation Area and Stoughton Pond Recreation Area are located nearby.

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
Price was $880, price is now $775 per person
$775
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.
Building is of historical interest, clean, comfortable, simple rooms, friendly staff.

Reviewed on Jul 31, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $623, price is now $550 per person
$550
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.
Beautiful resort. I love it!

Reviewed on Aug 4, 2026

Stockbridge Vacation Packages 3-4 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 $723, price is now $613 per person
$613
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Lebanon (LEB)
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,471, price is now $1,210 per person
$1,210
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $854, price is now $711 per person
$711
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Lebanon (LEB)
The Inn at Weathersfield

The Inn at Weathersfield

4 out of 5
Price was $842, price is now $719 per person
$719
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Lebanon (LEB)

Stockbridge Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Brook Road Inn

Brook Road Inn

3 out of 5
Price was $702, price is now $605 per person
$605
per person
Oct 10 - Oct 16
found 13 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Lebanon (LEB)

Top Flight Deals

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

United
Wed, Oct 14 - Tue, Oct 20
IAD
Washington Dulles Intl.
LEB
Lebanon Municipal
$364 Roundtrip, found 4 days ago
$364
Roundtrip
found 4 days ago
Select United flight, departing Wed, Oct 14 from Washington Dulles Intl. to Lebanon Municipal, returning Tue, Oct 20, priced at $364 found 4 days ago
Delta
Tue, Oct 13 - Tue, Oct 20
BWI
Baltimore Washington Intl. Thurgood Marshall
RUT
Rutland Southern Vermont Regional
$368 Roundtrip, found 2 days ago
$368
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 13 from Baltimore Washington Intl. Thurgood Marshall to Rutland Southern Vermont Regional, returning Tue, Oct 20, priced at $368 found 2 days ago
American Airlines
Tue, Sep 22 - Tue, Oct 6
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$474 Roundtrip, found 5 days ago
$474
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Oct 6, priced at $474 found 5 days ago
American Airlines
Sun, Sep 13 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$660 Roundtrip, found 3 days ago
$660
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Sep 13 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $660 found 3 days ago