Chester Depot Vacations from $955
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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.
Vikings Villages Resort
$955
per person
Dec 24 - Dec 29
found 16 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
10/10 Exceptional! (240 reviews)
Love our stay in Vikings. Staff was amazing and very attentive and helpful. The cabins were beautiful, clean and had everything we needed. Very recommended. Hope to go back in the future.
Reviewed on Oct 13, 2026
1846 Inn and Tavern
$1,162
per person
Dec 26 - Jan 2
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
10/10 Exceptional! (1 review)
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
Mountain Lodge at Okemo, A Vail Resorts Property
Clock Tower Base Area
$2,152
per person
Dec 25 - Dec 31
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8/10 Very Good! (225 reviews)
The condo we stay at was just okay. It could be a wonderful place, as the set up for two people was good, but is in desperate need of a thorough cleaning, painting, and general repair. Almost all the lights flickered off and on. The staff were wonderful. So nice and friendly and did respond to issues that developed (no heat in condo at first), extra towels, toilet paper … truly, the nicest staff at the front desk. We appreciated them so much
Reviewed on Oct 14, 2026
Chester Depot Hotel Deals
Fullerton Inn
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
$129 nightly
$141 total
Nov 10 - Nov 11
Total with taxes and fees
8.2/10 Very Good! (461 reviews)
"Stayed there 7yrs.ago and had another great experience this time, Cloe our waitress was excellent and made our dining alot of fun."
Reviewed on Oct 13, 2026
Jackson Gore Village, A Vail Resorts Property
111 Jackson Gore Road Ludlow VT
Fully refundableReserve now, pay when you stay
$199 nightly
$219 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (940 reviews)
"Beautiful place"
Reviewed on Oct 17, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$135 nightly
$146 total
Nov 16 - Nov 17
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
Bonnie's Bundles Dolls
7.6/10 (4 reviews)
Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views, or seek out its ski slopes.
DaVallia Art & Accents
10.0/10 (2 reviews)
Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.