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A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Chester
Vermont
United States of America
North America
Hotwire.com

Chester Flight + Hotel Packages

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

Deerfield Valley Inn

2 out of 5

Price was $491, price is now $442 per person

$442

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

New York (LGA) to Springfield (VSF)

Stay at this B&B in West Dover. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.

Vikings Villages Resort

2 out of 5

Price was $703, price is now $555 per person

$555

per person

Dec 11 - Dec 13

found 6 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Springfield (VSF)

Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Keets Brook Road Conservation Area are located nearby.

Chalet 239

2 out of 5

Price was $703, price is now $598 per person

$598

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

New York (LGA) to Springfield (VSF)

Stay at this motel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.

We loved how the room's and lobby were decorated, very cool.

Reviewed on Oct 13, 2026

Latchis Hotel

2.5 out of 5

Price was $795, price is now $686 per person

$686

per person

Dec 30 - Jan 2

found 6 hours ago

Roundtrip non-stop flight included

Miami (MIA) to Springfield (VSF)

Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.

Jackson Gore Village, A Vail Resorts Property

3 out of 5

Price was $966, price is now $871 per person

$871

per person

Nov 25 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) 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.

Everything met our expectations and we had a nice , relaxing time at the resort . We hiked up to the fire tower and was rewarded with spectacular views!

Reviewed on Oct 25, 2026

Woodstock Inn & Resort

4.5 out of 5

Price was $2,184, price is now $1,987 per person

$1,987

per person

Dec 30 - Jan 2

found 6 hours ago

Roundtrip non-stop flight included

Miami (MIA) 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 venue for our wedding!

Reviewed on Oct 25, 2026

Mount Snow Lodging by Vail Resorts

3 out of 5

Price was $928, price is now $845 per person

$845

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

New York (LGA) to Springfield (VSF)

Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and ski-in/ski-out access. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.

The bar tender in the lounge on Saturday 10/18 was not friendly. Seemed like he didn’t like his job. He was the only one working and there were not many customers at the bar. Dining room had no one in it. He just was not attentive to me party of 3 who just wanted to order a drink. Fitness center at the Season was very nice but hours were not very accommodating

Reviewed on Oct 20, 2025

1846 Inn and Tavern

3 out of 5

Price was $946, price is now $863 per person

$863

per person

Dec 30 - Jan 2

found 6 hours ago

Roundtrip non-stop flight included

Miami (MIA) to Springfield (VSF)

Stay at this inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.

The Inn also has an adjacent nice food tavern and music this weekend. Friendly host - embodied the helpful spirit of old inns. Helped with allowing a late dinner due to late arrival. Adjusted the heat for us and allowed us to set a bit extra in their library. Very welcoming. A ++ for hospitality and making us welcome!

Reviewed on Oct 12, 2026

Chester Vacation Packages 3-4 Night Stays

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

The Covered Bridge Inn

2.5 out of 5

Price was $476, price is now $409 per person

$409

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

New York (LGA) to Springfield (VSF)

The Shire Woodstock

3 out of 5

Price was $805, price is now $649 per person

$649

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Springfield (VSF)