Search Deals on
Woodstock Vacation Packages

Build your package with 2 more options

Woodstock Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Price was $710, price is now $623 per person
$623
per person
Oct 29 - 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 a free area shuttle. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall

Reviewed on Jul 19, 2026

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)
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Middle Covered Bridge are located nearby.
Amazing! Will visit again.

Reviewed on Aug 7, 2026

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Price was $859, price is now $734 per person
$734
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) 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.
Enjoyable and beautiful place. Ann

Reviewed on Jul 20, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $731, price is now $625 per person
$625
per person
Oct 29 - 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

Deer Brook Inn

Deer Brook Inn

3 out of 5
Price was $1,161, price is now $994 per person
$994
per person
Oct 29 - 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.

Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts

4 out of 5
Price was $783, price is now $678 per person
$678
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.

Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
Price was $735, price is now $642 per person
$642
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)
Stay at this vacation home in Ludlow. Enjoy free parking, laundry facilities, and cable TV channels. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.

Reviewed on Jun 26, 2025

Stay At Jimmy's

Stay At Jimmy's

3 out of 5
Price was $922, price is now $806 per person
$806
per person
Oct 29 - 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 breakfast, free WiFi, and free parking. Popular attractions Quechee Gorge Bridge and Billings Park and Trail are located nearby.
The room and amenities exceeded our expectations. It was the best B & B we ever stayed in. The location was near shopping, restaurants and hiking trails. I highly recommend. You will not be disappointed.

Reviewed on Jul 29, 2026

Woodstock Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $731, price is now $625 per person
$625
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)
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)
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $859, price is now $734 per person
$734
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)
Deer Brook Inn

Deer Brook Inn

3 out of 5
Price was $1,161, price is now $994 per person
$994
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)

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 3 days ago
$368
Roundtrip
found 3 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 3 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