Chester Vacation Packages

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Your Chester Vacation

Excellent adventures await when you reserve a Chester vacation package. Whether you're a history buff, art enthusiast or just a traveler who loves to experience new places, there's something for everyone in this lively city. Need some ideas on what to see or do first during your trip to Chester? Don't miss leading attractions like DaVallia Art & Accents. Your ultimate Chester vacation is just clicks away. Search flights, accommodations and more on Expedia for a trip that's tailored to suit your travel style.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was CA $818, price is now CA $785 per person
CA $785
per person
Oct 3 - Oct 5
found 4 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Springfield (VSF)
8.6/10 Excellent! (751 reviews)
Electric car chargers are not in the buildings anymore. Inconvenient.

Reviewed on Aug. 21, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,958, price is now CA $1,528 per person
CA $1,528
per person
Oct 3 - Oct 5
found 4 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Springfield (VSF)
8.8/10 Excellent! (806 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

Inn At Mount Snow

Inn At Mount Snow

2 out of 5
Price was CA $1,109, price is now CA $1,049 per person
CA $1,049
per person
Oct 3 - Oct 5
found 4 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Springfield (VSF)
10/10 Exceptional! (21 reviews)
Staff was so knowledgeable and welcoming. A great stay!

Reviewed on Aug. 18, 2025

Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was CA $858, price is now CA $820 per person
CA $820
per person
Oct 3 - Oct 5
found 4 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Springfield (VSF)
8.8/10 Excellent! (23 reviews)
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was CA $937, price is now CA $899 per person
CA $899
per person
Oct 3 - Oct 5
found 4 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Springfield (VSF)
8.6/10 Excellent! (214 reviews)
The hotel has a 4:00 check-in which is later than most. We called a week in advance to request an early check-in as we were attending a local wedding that was called for 4:15 and we wanted to be able to get in our room to get ready as we were coming from out of state. They said they couldn’t guarantee anything, but to call back the day before. We did as they suggested and not only would they still not guarantee our request, the man at the front desk could not be less accommodating. As it turns out, we did get into our room at 3:00, but at that point we had already prepared for being unable to get into a room. The room itself was uncomfortable, and uninviting. The sheets weren’t soft or tucked fully under the mattress. Lamps and the alarm clock were left unplugged requiring us to move furniture to plug them in and a bottle of disinfectant was left in our bathroom. Needless to say we won’t be back.

Reviewed on Aug. 18, 2025

Ready to book your vacation to Chester?

 

Choose your dates

Chester 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 $192 per night from Sep 1 to Sep 2
CA $192
CA $209 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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $565 per night from Sep 1 to Sep 2
CA $565
CA $683 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (532 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul. 30, 2025

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Aug 26 to Aug 27
CA $165
CA $192 total
Aug 26 - Aug 27
includes taxes & fees
8.6/10 Excellent! (807 reviews)
"Forth time at The Shire, everything was wonderful!!"

Reviewed on Aug. 21, 2025

The Shire Woodstock
See all 2,951 properties in Chester
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 vacation package cost?
You'll find cheap prices from CA $785 on Expedia for your Chester escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
You can usually find reduced prices and better availability in March, May and June. Take a look at our cheap Chester vacation packages and you could score some great off-season discounts.
How many days is enough for Chester?
The ideal length of your Chester vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to check out all the top attractions and discover some hidden gems along the way.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most economical Chester package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and accommodations separately. Better still, you can customize your Chester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Chester?
If you're planning a spontaneous Chester getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Chester?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Chester.
  2. Set a budget: Consider costs like flights, food and transportation when working out how much to set aside for your trip to Chester. Then, pick a property that works with your budget, whether that's a wallet-friendly option or a swankier getaway.
  3. Decide your trip length: Think about how much time you want to spend discovering Chester. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Chester vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.