Chester Depot Vacation Packages
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Top Holiday Package Deals in Chester Depot
Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn
CA $1,414
per person
Oct 14 - Oct 21
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.4/10 Exceptional! (132 reviews)
We returned to this place on a quick 2-day/last minute get away. Owner is new from last time. Nice people; helpful and made a very good breakfast. Only issue we really had was the plumbing. Our room had some kind of venting issue with the sink/toilet/shower. Toilet bubbled and would go down at times; sink would go slow/stop at times; shower also stopped up and went down very slow. Told the owner about it and hopefully they can get it fixed. But overall, pleasant stay.
Reviewed on Aug 17, 2026
Woodstock Inn & Resort
CA $2,339
per person
Oct 23 - Oct 26
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
9.4/10 Exceptional! (599 reviews)
Our room was beautiful, clean, and quiet. The bed was comfortable, and the amenities in the bathroom were a real indulgence.
Reviewed on Sep 1, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
CA $1,521
per person
Oct 14 - Oct 21
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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, A Vail Resorts Property
Clock Tower Base Area
CA $1,473
per person
Oct 14 - Oct 21
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8/10 Very good! (225 reviews)
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall
Reviewed on Jul 19, 2026
Chester Depot Hotel Deals
Fullerton Inn
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
CA $193
CA $210 total
Sep 8 - Sep 9
includes taxes & fees
8.2/10 Very good! (451 reviews)
"No elevator. I’m too old to drag my luggage up 3 flights of stairs. And it was hot up there. There isn’t much in this small town to eat, and they all open late & close early. Dinner at the hotel was pricey, but I had the best cheeseburger I’ve had in quite some time."
Reviewed on Sep 1, 2026
Historic 150-year-old farmhouse, Jacuzzi included
Chester VT
CA $188
CA $591 total
Sep 8 - Sep 9
includes taxes & fees
9.6/10 Exceptional! (20 reviews)
"Great place for a large group hot tub and fire pit were fun."
Reviewed on Aug 29, 2026
Jackson Gore Village, A Vail Resorts Property
111 Jackson Gore Road Ludlow VT
Fully refundableReserve now, pay when you stay
CA $242
CA $294 total
Sep 30 - Oct 1
includes taxes & 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.
Frequently asked questions
How much does a Chester Depot vacation package cost?
From as low as CA $1,414. Yes, you read that correctly. Our Chester Depot vacation packages are a simple way to make your dollar go further. Combine your hotels, flights and rental car and get to know this fabulous destination.
How do I get a cheap travel package to Chester Depot?
Just imagine all the amazing things you could do in Chester Depot with a pile of extra cash in your pocket. Watch your savings stack up when you combine your travel bookings into a Chester Depot vacation package. You have plenty of choice when you book your trip with Expedia too. In fact, you can select from more than 550 air carriers and 1,000,000 properties throughout the world. Whether you're taking a break with the family or surprising your special someone, planning a trip to Chester Depot is better with a package.
Where should I stay in Chester Depot?
Chester Depot features several popular places to discover, including DaVallia Art & Accents. Stay somewhere close by and make sightseeing simple.
What are the top hotels in Chester Depot?
Fullerton Inn and Spacious 1 - Level Ranch, Mtn. Views are a couple of the most popular properties in Chester Depot. Why not have a look at the amenities and rates at each and then make a decision?
How far in advance should I book my Chester Depot vacation?
It's tricky picking the ideal time for airfares, but we generally say the earlier, the better. Most international flights on Expedia become available up to 12 months in advance. If you're unable to do so, don't despair. Cheap prices appear from time to time just weeks before departure dates.
What does an Expedia Chester Depot travel package include?
Hotels, flights and rental cars, or any combination of them — the choice is all yours! Whether you're venturing to Chester Depot with the kids or adventuring with your friends, there's a bundle to match your style and budget. Once you've made your booking, why not add on some tours or activities?
What should I know before booking a Chester Depot travel package?
Tailor deals that fit your budget with an Expedia package. Airfares, hotels, rental cars — we have them all. You'll save precious cash just for combining your bookings. Whether you're embarking on a skiing adventure or venturing someplace warm, your dream vacation is only a few clicks away.
Can I choose my airline with a Chester Depot Expedia vacation package?
With a vacation package, you're the boss. Whether you'd like to fly to Chester Depot in economy or first class, simply select from the available airline options. Expedia has access to more than 550 partner airlines all over the world.
If I'm not able to travel, can I cancel my Chester Depot vacation package?
Whether it's your flight or hotel, you can cancel or amend it. Booked your Chester Depot vacation package in the last 24 hours? You may be able to make any changes for free. For bookings made more than 24 hours ago, you may be charged a fee by your hotel, airline or car rental company. For more details, take a look at our Customer Service Portal. We're here to help you every step of the way.
Stay near popular Chester Depot attractions
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.