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, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was CA $1,442, price is now CA $1,063 per person
CA $1,063
per person
Aug 18 - Aug 25
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (862 reviews)
Staff was super friendly at check-in. Room was very clean and quiet. The location was fantastic as we stayed on 4th of july weekend so fireworks were right down the road. Close to quite a few great things about the area. We had breakfast at the Tavern both mornings and it was quite good and not nearly as expensive as you might expect it to be in this type of resort.

Reviewed on Jul 7, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $2,961, price is now CA $2,067 per person
CA $2,067
per person
Aug 18 - Aug 25
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Springfield (VSF)
8.8/10 Excellent! (954 reviews)
Absolutely beautiful setting! The room was better than expected-- spacious, clean and gorgeously decorated. The location was also great-- everything was walkable. Highly recommend.

Reviewed on Jul 5, 2026

Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
Clock Tower Base Area
Price was CA $2,017, price is now CA $1,506 per person
CA $1,506
per person
Aug 18 - Aug 25
found 1 hour ago
Roundtrip flight included
Montreal (YUL) 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

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 $1,860, price is now CA $1,396 per person
CA $1,396
per person
Aug 18 - Aug 25
found 1 hour ago
Roundtrip flight included
Montreal (YUL) 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 $1,621, price is now CA $1,229 per person
CA $1,229
per person
Aug 18 - Aug 25
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Springfield (VSF)
7.8/10 Good! (35 reviews)

Ready to book your vacation to Chester?

 

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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 $225 per night from Jul 11 to Jul 12
CA $225
CA $246 total
Jul 11 - Jul 12
includes taxes & fees
8.2/10 Very good! (441 reviews)
"The building was very quaint and had a historical vibe."

Reviewed on Jul 7, 2026

Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $792 per night from Aug 5 to Aug 6
CA $792
CA $934 total
Aug 5 - Aug 6
includes taxes & fees
9.4/10 Exceptional! (589 reviews)
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."

Reviewed on Jun 25, 2026

Woodstock Inn & Resort
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Jul 12 to Jul 13
CA $169
CA $183 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
"Great place to stay while visiting Keene. This hotel is close to all the amenities Keene has to offer. Our room was spacious and clean. The hotel looks as though it’s been recently updated. The breakfast was very good with lots of variety. The staff was kind. Dillion was eager to help with anything ..."

Reviewed on Jul 9, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
See all 3,100 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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Stay near popular Chester attractions

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.
See properties

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $1,063 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.

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