Name: Jackson Gore Village
Price range: $213 total
Rating: 8.4

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.

Colonial Motel And Spa

$724

per person

Nov 26 - Nov 30

found 4 hours ago

Roundtrip flight included

Orlando (MCO) to Springfield (VSF)

6.8/10 (1,004 reviews)

Location and parking are perfect for us. Also the price for the size of the room that we get is definitely fair. We stay here every time I come visit my family.

Reviewed on Oct 6, 2025

The Covered Bridge Inn

$817

per person

Nov 26 - Nov 30

found 4 hours ago

Roundtrip flight included

Orlando (MCO) to Springfield (VSF)

7.8/10 Good! (1,003 reviews)

Very clean besides mold on shower, just needs to be scrubbed with bleach.

Reviewed on Oct 12, 2025

Mount Snow Grand Summit Resort

$1,329

per person

Dec 26 - Dec 29

found 14 hours ago

Roundtrip non-stop flight included

Miami (MIA) to Springfield (VSF)

8.8/10 Excellent! (223 reviews)

The staff were all very friendly and nice, especially the lady who helped us at the s’mores station! The room was very clean. The ski left was under maintenance which was disappointing but otherwise this was an amazing place to stay.

Reviewed on Oct 12, 2025

Deerfield Valley Inn

$1,011

per person

Nov 28 - Nov 30

found 1 day ago

Roundtrip flight included

New York (JFK) to Springfield (VSF)

9.6/10 Exceptional! (64 reviews)

We loved our stay in Deerfield Valley Inn. One of the best inns in Southern Vermont that we stayed in. The room was spacious, cozy, clean and elegantly decorated with a fireplace. The staff were super friendly and accommodating. The inn was right in the middle of the town so everything was walking distance. Definitely going back and highly recommend for a relaxing getaway.

Reviewed on Sep 25, 2025

Latchis Hotel

$754

per person

Nov 26 - Nov 30

found 4 hours ago

Roundtrip flight included

Orlando (MCO) to Springfield (VSF)

8.4/10 Very Good! (789 reviews)

Convenient to the Latchis Theatre, however the downtown area around the hotel has many vacant storefronts, so not really many things to do close by. We didnt feel safe going out after dark. Perhaps those are just first impressions of an out of towner, who with time could have grown to find it quaint. The staff was friendly at both the hotel and the restaurant we found a couple of blocks away.

Reviewed on Oct 7, 2025

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

8/10 Very Good! (383 reviews)

"The Fullerton Inn was perfect for our visit to the area. The Inn was quaint, room comfortable, dinner was great and the staff were friendly and helpful."

Reviewed on Oct 5, 2025

Pointe at Castle Hill Resort

2940 State Route 103, Cavendish, VT

$136 nightly

$148 total

Oct 19 - Oct 20

Total with taxes and fees

8.6/10 Excellent! (901 reviews)

"Gorgeous suite, staff was so nice and helpful."

Reviewed on Oct 7, 2025

Jackson Gore Village

111 Jackson Gore Road, Ludlow, VT

Fully refundableReserve now, pay when you stay

$193 nightly

$213 total

Nov 12 - Nov 13

Total with taxes and fees

8.4/10 Very Good! (785 reviews)

"good stay"

Reviewed on Oct 7, 2025

See all 1,573 properties in Chester Depot

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.