Chester Flight + Hotel Packages

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

Mountain Lodge at Okemo, A Vail Resorts Property

$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

$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.

Winterplace at Okemo, A Vail Resorts Property

$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

$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

$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

$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

$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

$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

Chester Vacation Packages 3-4 Night Stays

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