Chester Depot Vacations from $591
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Your Chester Depot Vacation
Make planning your travels easy by creating a vacation package to Chester Depot. We'll handle the specifics, so you can concentrate on discovering everything this neighborhood has to offer. If you're in the mood to sightsee, no trip to Chester Depot is complete without a visit to nearby DaVallia Art & Accents. Don't just wish for it — take action! Lock in your perfect Chester Depot vacation with Expedia and enjoy traveling your way.
The Latest Chester Depot Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
Price was $2,270, price is now $1,906 per person
$1,906
per person
Dec 19 - Dec 22
found 16 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Springfield (VSF)
7.6/10 Good! (31 reviews)
Don’t ever rent at this place for the condo rentals they sent us to the wrong address, I could not get in contact with the so-called property manager for over an hour or more. We had no toilet paper, we had no hairdryer, no paper towels, we didn’t even know where the keys were or shampoo or soap. Basically this was an utter disaster. I tried to work it out with resort management and they offered certain things and I countered and I got at that point what I wanted, but it just continued to spiral downhill and then when I communicate further issues, I had to be on the phone with them, trying to explain to them what the problem was up until 11 PM at night, that night was in the 30s and they left the air conditioner on in the house didn’t warm up until after 1 AM. This was by far the worst experience I’ve ever had with a supposedly high-end resort. I’m telling you do not rent from their condo selection. It’s terrible. It’s expensive and it is just a waste of time.
Reviewed on Oct 15, 2026
Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was $1,621, price is now $1,407 per person
$1,407
per person
Dec 19 - Dec 22
found 16 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Springfield (VSF)
8.8/10 Excellent! (28 reviews)
Large unit - well laid out for three generation visit. Comfortable beds. Kitchen well appointed.
Reviewed on Oct 20, 2026
Chester Depot Hotel Deals
Fullerton Inn
40 The Common Chester VT
$129 nightly
The price is $141 total per night from Nov 10 to Nov 11
$141 total
Nov 10 - Nov 11
Total with taxes and fees
Jackson Gore Village, A Vail Resorts Property
111 Jackson Gore Road Ludlow VT
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $222 total per night from Dec 7 to Dec 8
$222 total
Dec 7 - Dec 8
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
5 Village Lodge Road Stratton VT
$149 nightly
The price is $164 total per night from Nov 15 to Nov 16
$164 total
Nov 15 - Nov 16
Total with taxes and fees
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.
Stay near popular Chester Depot attractions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.