Chester Depot Vacations from $674
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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.
Jackson Gore Village
Jackson Gore Base Area
Save 100% on your flight
Price was $2,067, price is now $1,569 per person
$1,569
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good.
Reviewed on Nov 30, 2025
Okemo Mountain Lodging
Clock Tower Base Area
Save 100% on your flight
Price was $3,663, price is now $2,822 per person
$2,822
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
7.8/10 Good! (28 reviews)
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
Mountain Lodge at Okemo
Clock Tower Base Area
Save 100% on your flight
Price was $1,843, price is now $1,458 per person
$1,458
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8/10 Very Good! (219 reviews)
We really enjoyed our stay at the Mountain Lodge at Okemo, it was clean and our room was newly renovated and very cute. Would definitely recommend!!
Reviewed on Oct 6, 2025
Chester Depot Hotel Deals
Fullerton Inn
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $141 total per night from Dec 2 to Dec 3
$141 total
Dec 2 - Dec 3
Total with taxes and fees
8/10 Very Good! (402 reviews)
quaint.
Reviewed on Oct 24, 2025
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$146 nightly
The price is $159 total per night from Dec 7 to Dec 8
$159 total
Dec 7 - Dec 8
Total with taxes and fees
8.6/10 Excellent! (920 reviews)
Loved our room. Very clean and enjoyed fireplace. Only thing we were bothered by was noise outside our room probably connected to pool heater or filter.
Reviewed on Nov 11, 2025
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road Brownsville VT
Fully refundable
$106 nightly
The price is $115 total per night from Dec 8 to Dec 9
$115 total
Dec 8 - Dec 9
Total with taxes and fees
8.8/10 Excellent! (775 reviews)
Very welcoming, spacious, clean. Perfect for a family of 4.
Reviewed on Nov 18, 2025
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.
Discover the most popular places to visit in Chester Depot
Bonnie's Bundles Dolls
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
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.