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.
The Hartness House
CA $1,029
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Springfield (VSF)
8.2/10 Very good! (349 reviews)
Beautiful grounds and common areas. Room was plain which was fine but a/c was inefficient and the bed was just ok. K-cups are not coffee in my book, and we had better pastry elsewhere. The location was great for us, the town is cute. Everything was closed on Sunday so we headed to Chester which is close and adorable too. All the towns shut down early so plan accordingly even restaurants and ice cream places. Vermont is gorgeous and friendly. If you get a chance, do go.
Reviewed on Aug 4, 2026
Hideaway Inn Mt. Snow
CA $1,599
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Springfield (VSF)
8.6/10 Excellent! (121 reviews)
Weird robot-like hotel with no staff on site when we arrived. Check-in was online, a bit confusing (even for the young people in our party), and cameras in common areas monitoring everyone felt dystopian. Rooms were tiny, but well-appointed. Strange stay.
Reviewed on Aug 4, 2026
Deerfield Valley Inn
CA $1,649
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Springfield (VSF)
9.4/10 Exceptional! (128 reviews)
Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place
Reviewed on Jul 25, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
CA $1,199
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Vancouver (YVR) 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
Ready to book your vacation to Chester?
Chester Hotel Deals
Fullerton Inn
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
CA $194
CA $211 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very good! (446 reviews)
"The rooms are very clean. I had no problem with any of that. We went downstairs and told the manager that the bathroom sink was not draining and he said he would take care of it and he did we got back from where we had gone for the day it was working. We had our breakfast between eight and 11 is ..."
Reviewed on Aug 3, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
CA $570
CA $688 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (598 reviews)
"Amazing! Will visit again."
Reviewed on Aug 7, 2026
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
CA $160
CA $173 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"Breakfast offered a lot of good choices from eggs to cereal to fresh fruit. The room was clean throughout and the AC quiet and efficient. The staff was excellent in providing information and Dillan's recommendation for dinner was "spot on". The room price was very reasonable, and the indoor heated ..."
Reviewed on Aug 7, 2026
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.
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.
Bonnie's Bundles Dolls
7.6/10 (4 reviews)
Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views, or seek out its ski slopes.
Frequently asked questions
How much does a Chester vacation package cost?
You'll find cheap prices from CA $1,029 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?
- 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.
- 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.
- 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.
- 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.
