Chester Depot Vacations from $535
Book a Hotel + Flight or Car together to unlock savings
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.
Mountaineer Inn
Price was $641, price is now $535 per person
$535
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Springfield (VSF)
8.8/10 Excellent! (501 reviews)
Easy in and out. All transactions with this property are handled online; there was no person-to-person interaction while on the site. The rooms and bathrooms were clean, and the beds were comfortable. We'd consider this again in the future.
Reviewed on Aug 23, 2025
The Shire Woodstock
Save 100% on your flight
Price was $2,017, price is now $1,471 per person
$1,471
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Springfield (VSF)
8.8/10 Excellent! (811 reviews)
Comfortable bed, linens, fridge. Beautiful views of the river. Wonderful staff. Truly is one of our happy places.
Reviewed on Sep 2, 2025
Chester Depot Hotel Deals
Fullerton Inn
40 The Common, Chester, VT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $152 total per night from Sep 4 to Sep 5
$152 total
Sep 4 - Sep 5
Total with taxes and fees
Pointe at Castle Hill Resort
2940 State Route 103, Cavendish, VT
$129 nightly
The price is $140 total per night from Sep 16 to Sep 17
$140 total
Sep 16 - Sep 17
Total with taxes and fees
Jackson Gore Village
111 Jackson Gore Road, Ludlow, VT
Fully refundableReserve now, pay when you stay
$205 nightly
The price is $226 total per night from Sep 4 to Sep 5
$226 total
Sep 4 - Sep 5
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.
Discover the most popular places to visit in Chester Depot
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.