Chester Depot Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • Property amenity
    Jul 6 - Jul 10

    Hideaway Inn Mt. Snow + Flight

    West Dover
    4 nights
    3.0 star property
    8.8/10 - Excellent (101 reviews)
    "There is no staff at the facility but someone is available by text The common areas were great. I can see how this would be a good communal area to meet others in the busy months or go with a big group of friends. I loved the work from home room. The outdoor areas were really nice too. Unfortunately the entry keypad into my room was very finicky. It would take me multiple tries each time entering my room to hit the numbers just right. My toilet seat in the bathroom was also completely broken..."
    Reviewed May 22, 2026
    Roundtrip • Toronto (YYZ) - Albany (ALB)
    YYZ - ALB • 1 stop ALB - YYZ • 1 stop
    CA $1,052
    CA $973
    per traveller
    found 20 hours ago
    Hideaway Inn Mt. Snow
  • Property entrance
    Jul 20 - Jul 25

    Jackson Gore Village, A Vail Resorts Property + Flight

    Jackson Gore Base Area
    5 nights
    3.0 star property
    8.6/10 - Excellent (854 reviews)
    "I’ve stayed here with my two daughters multiple times and it’s always incredible."
    Reviewed May 17, 2026
    Roundtrip • Calgary (YYC) - Albany (ALB)
    YYC - ALB • 1 stop ALB - YYC • 1 stop
    CA $1,618
    CA $1,356
    per traveller
    found 1 day ago
    Jackson Gore Village, A Vail Resorts Property
  • Exterior
    Jul 6 - Jul 10

    Latchis Hotel + Flight

    Brattleboro
    4 nights
    2.5 star property
    8.6/10 - Excellent (893 reviews)
    "The front desk staff was courteous and the cheese platter at Sage was excellent."
    Reviewed June 3, 2026
    Roundtrip • Toronto (YYZ) - Albany (ALB)
    YYZ - ALB • 1 stop ALB - YYZ • 1 stop
    CA $1,193
    CA $1,068
    per traveller
    found 20 hours ago
    Latchis Hotel
  • Lobby
    Jul 20 - Jul 25

    Holiday Inn Express Hotel & Suites Brattleboro by IHG + Flight

    Brattleboro
    5 nights
    2.5 star property
    8.8/10 - Excellent (1,001 reviews)
    "Very clean and helpful staff. Breakfast was pretty good"
    Reviewed May 23, 2026
    Roundtrip • Calgary (YYC) - Albany (ALB)
    YYC - ALB • 1 stop ALB - YYC • 1 stop
    CA $1,829
    CA $1,654
    per traveller
    found 1 day ago
    Holiday Inn Express Hotel & Suites Brattleboro by IHG
  • Exterior
    Jul 6 - Jul 10

    Grand Summit Resort, A Vail Resorts Property + Flight

    West Dover
    4 nights
    3.0 star property
    8.6/10 - Excellent (270 reviews)
    "It’s a nice resort"
    Reviewed June 1, 2026
    Roundtrip • Toronto (YYZ) - Albany (ALB)
    YYZ - ALB • 1 stop ALB - YYZ • 1 stop
    CA $1,168
    CA $1,080
    per traveller
    found 20 hours ago
    Grand Summit Resort, A Vail Resorts Property

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 $193 per night from Jun 11 to Jun 12
CA $193
CA $210 total
Jun 11 - Jun 12
includes taxes & fees
8.2/10 Very Good! (435 reviews)
"Very nice older Inn with on-site tavern in a classic Vermont town. Quite and comfortable stay."

Reviewed on May 22, 2026

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

Historic 150-year-old farmhouse, Jacuzzi included

Chester VT
The price is CA $238 per night from Jun 9 to Jun 10
CA $238
CA $656 total
Jun 9 - Jun 10
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
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
Fully refundable
The price is CA $207 per night from Jun 7 to Jun 8
CA $207
CA $249 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (836 reviews)
"Just perfect!"

Reviewed on Jun 3, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
See all 1,471 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 . 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.