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.
Latchis Hotel
CA $971
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (992 reviews)
Had a wonderful stay. Great room with a beautiful view of the mountains. And we absolutely loved that every room had a record player with historic records to play and enjoy - what a cool feature!
Reviewed on Oct 18, 2026
Sinclair Inn Bed and Breakfast
CA $1,104
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (127 reviews)
We had a wonderful stay at the Sinclair Inn Bed & Breakfast in Jericho, Vermont! The house is absolutely beautiful—a charming Queen Anne Victorian filled with character and historic charm. We stayed in Room 5 upstairs, which featured a comfortable king bed and a private bathroom. It was a lovely, comfortable place to relax and enjoy our visit.
Kyle, Holly, and their daughter Cassidy were amazing hosts! They went above and beyond to make us feel welcome. Earlier in our trip, before arriving at the Sinclair Inn, I had injured myself and was on crutches. When we arrived, Kyle graciously helped my wife carry our suitcases upstairs to our room. That thoughtful gesture meant so much to us and really showed the kindness and genuine hospitality of this wonderful family.
Breakfast was delicious, and one of the things we especially enjoyed was the opportunity to sit down, meet, and talk with the other guests. Those conversations added a personal touch to our stay and made the experience even more enjoyable.
Between the beautiful Victorian home, the comfortable accommodations, the delicious breakfast, and the outstanding hospitality, our stay was truly memorable. We highly recommend the Sinclair Inn to anyone visiting Vermont. If you're looking for a beautiful bed and breakfast with wonderful hosts who genuinely care about their guests, this is the place! We would absolutely love to stay here again.
Reviewed on Oct 18, 2026
1846 Inn and Tavern
CA $1,240
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Chester Depot Hotel Deals
Fullerton Inn
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
CA $182
CA $199 total
Nov 10 - Nov 11
includes taxes & 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
CA $261
CA $317 total
Nov 18 - Nov 19
includes taxes & fees
8.6/10 Excellent! (948 reviews)
"My husband and I went for weekend trip. Our stay couldn’t be more wonderful. The front desk was helpful. The rooms had toiletries and were clean. We didn’t expect a refrigerator in room, but was in room. Since off season, the garage parking was vey convenient and ample."
Reviewed on Oct 20, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
CA $215
CA $245 total
Oct 28 - Oct 29
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Rooms are clean and comfortable. The overall appearance is a little dated but didn’t take away from the experience. We were in the area for the fall leaves and enjoyed the proximity to many small towns and hiking areas."
Reviewed on Oct 20, 2026
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 $928. 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
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.