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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was CA $1,381, price is now CA $1,221 per person
CA $1,221
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Calgary (YYC) 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

The Shire Woodstock

3 out of 5
Price was CA $3,248, price is now CA $2,507 per person
CA $2,507
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (811 reviews)
This is a perfect family oriented spot for visiting downtown Woodstock. We stayed in one of their family suites. It was spacious and comfortable without being ostentatious. Loved the details in the outdoor space--well tended plants and flowers, as well as, fire pits and Adirondack chairs to hang out by the river.

Reviewed on Aug. 18, 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was CA $2,911, price is now CA $2,356 per person
CA $2,356
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
9.6/10 Exceptional! (62 reviews)
Very authentic and comfortable.

Reviewed on Aug. 22, 2025

Chalet 239

Chalet 239

2 out of 5
Price was CA $1,600, price is now CA $1,384 per person
CA $1,384
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
9.4/10 Exceptional! (74 reviews)
Teh staff were friendly and helpful. Immediately upon booking I received a text message from the staff letting me know someone was there to help with any questions. checking in was easy and the hotel was very clean. The room, beds and bathroom were all clean and well kept. The free breakfast was a plus.

Reviewed on Aug. 12, 2025

Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was CA $1,579, price is now CA $1,457 per person
CA $1,457
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (23 reviews)

Chester Depot Hotel Deals

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common, Chester, VT
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Sep 1 to Sep 2
CA $191
CA $208 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (371 reviews)
Great Inn in a quaint town.
"A wonderful little Inn with such a pleasant owner and just a great vibe there. Would absolutely recommend for a summer or winter stay. Can imagine it is beautiful in the winter."

Reviewed on Aug. 3, 2025

Fullerton Inn
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road, Brownsville, VT
The price is CA $178 per night from Sep 14 to Sep 15
CA $178
CA $213 total
Sep 14 - Sep 15
includes taxes & fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103, Cavendish, VT
The price is CA $177 per night from Sep 1 to Sep 2
CA $177
CA $202 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (870 reviews)
"Friendly staff"

Reviewed on Aug. 25, 2025

Pointe at Castle Hill Resort
See all 1,575 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.
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Frequently asked questions

How much does a Chester Depot vacation package cost?
From as low as CA $1,221. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.