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A forest with autumn foliage in various colors.

Chester Depot Vacations from $712

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The Latest Chester Depot Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Property entrance
    Sep 24 - Sep 28

    Jackson Gore Village, A Vail Resorts Property + Flight

    Jackson Gore Base Area
    4 nights
    3.0 star property
    8.6/10 - Excellent (870 reviews)
    "Great family friendly location!"
    Reviewed July 11, 2026
    Roundtrip • Denver (DEN) - Springfield (VSF)
    DEN - ALB • 1 stop ALB - DEN • Nonstop
    $832
    $712
    per traveler
    found 16 hours ago
    Jackson Gore Village, A Vail Resorts Property
  • Front of property
    Sep 24 - Sep 28

    Vikings Villages Resort + Flight

    Guilford
    4 nights
    2.0 star property
    10/10 - Exceptional (208 reviews)
    "Beautiful place, extraordinary, Christina was so kind and accommodating."
    Reviewed July 15, 2026
    Roundtrip • Denver (DEN) - Springfield (VSF)
    DEN - ALB • 1 stop ALB - DEN • Nonstop
    $1,067
    $833
    per traveler
    found 16 hours ago
    Vikings Villages Resort
  • Exterior
    Sep 24 - Sep 28

    Latchis Hotel + Flight

    Brattleboro
    4 nights
    2.5 star property
    8.6/10 - Excellent (931 reviews)
    "The uniqueness of the '30s/40's era vibe brought us back for another visit.It was like stepping back in time. The movie theaters are classic. Sages is the adjoining cocktail lounge complete with cosy,stuffed chairs,40's style decor.Again, we felt like we stepped back in time. The cocktails were quite unusual and thoughtful and we wish we could have tried them all. Tapas and waffles! So yummy. The staff at the hotel were gracious, friendly, helpful.And there was a never-ending supply of plain or..."
    Reviewed July 16, 2026
    Roundtrip • Denver (DEN) - Springfield (VSF)
    DEN - ALB • 1 stop ALB - DEN • Nonstop
    $911
    $755
    per traveler
    found 16 hours ago
    Latchis Hotel
  • Front of property
    Oct 1 - Oct 6

    Stone Hearth Inn and Eatery + Flight

    Chester
    5 nights
    3.0 star property
    9.2/10 - Wonderful (120 reviews)
    "Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
    Reviewed June 14, 2026
    Roundtrip • Houston (HOU) - Springfield (VSF)
    IAH - RUT • 2 stops RUT - IAH • 2 stops
    $1,457
    $1,239
    per traveler
    found 14 hours ago
    Stone Hearth Inn and Eatery
  • Exterior
    Oct 1 - Oct 6

    Mount Snow Lodging by Vail Resorts + Flight

    West Dover
    5 nights
    3.0 star property
    7.8/10 - Good (23 reviews)
    "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 October 20, 2025
    Roundtrip • Houston (HOU) - Springfield (VSF)
    IAH - RUT • 2 stops RUT - IAH • 2 stops
    $1,258
    $1,098
    per traveler
    found 14 hours ago
    Mount Snow Lodging by Vail Resorts

Chester Depot Hotel Deals

Garden

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (441 reviews)
"The building was very quaint and had a historical vibe."
$159 nightly
The price is $173
Jul 18 - Jul 19
Total with taxes and fees
Fullerton Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Chester Depot
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.