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.
Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Clock Tower Base Area
Price was CA $1,244, price is now CA $1,085 per person
CA $1,085
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
8/10 Very Good! (222 reviews)
Great location. Staff slow to respond.

Reviewed on Feb 21, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was CA $1,362, price is now CA $1,144 per person
CA $1,144
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
8.6/10 Excellent! (851 reviews)
No inflatable mattress offered anymore.

Reviewed on Mar 18, 2026

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was CA $1,500, price is now CA $1,275 per person
CA $1,275
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts

4 out of 5
Clock Tower Base Area
Price was CA $1,364, price is now CA $1,174 per person
CA $1,174
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
7.8/10 Good! (35 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.

Reviewed on Oct 8, 2025

Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
Clock Tower Base Area
Price was CA $1,281, price is now CA $1,112 per person
CA $1,112
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) 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

Chester Depot Hotel Deals

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
The price is CA $179 per night from Apr 28 to Apr 29
CA $179
CA $195 total
Apr 28 - Apr 29
includes taxes & fees
8.2/10 Very Good! (430 reviews)
The carpets could have been vacuumed and it was overpriced for what it was.

Reviewed on Apr 10, 2026

Fullerton Inn
Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included

Chester VT
The price is CA $187 per night from Apr 16 to Apr 17
CA $187
CA $589 total
Apr 16 - Apr 17
includes taxes & fees
9.8/10 Exceptional! (16 reviews)
We had a great (but short!) stay at the Farmhouse. We used this as our base to tour colleges in the greater area, and we wish we had more time to enjoy the home. It was great to be able to soak in the hot tub, cook dinner, and relax after days of walking and driving.The home had lots of charm, and ...

Reviewed on Apr 2, 2026

Historic 150-year-old farmhouse, Jacuzzi included
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 $220 per night from May 2 to May 3
CA $220
CA $251 total
May 2 - May 3
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Room was perfect (king bed), and big. Hot tub was wonderful after skiing all day and hot, but jets could have been stronger. Staff efficient and very friendly. Location great-10 minutes from Okemo. Will definitely come back!

Reviewed on Apr 10, 2026

Pointe at Castle Hill Resort
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Frequently asked questions

How much does a Chester Depot vacation package cost?
From as low as CA $1,085. 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.