Chester Holidays
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Top Flight + Hotel Deals in Chester
Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo, A Vail Resorts Property
Clock Tower Base Area
€577
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Springfield (VSF)
8/10 Very good! (225 reviews)
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall
Reviewed on 19 Jul 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
€736
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) 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 26 Jun 2025
Top hotels in Chester
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
€423
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (599 reviews)
"Amazing! Will visit again."
Reviewed on 7 Aug 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
€242
9 Sept - 10 Sept
includes taxes & fees
9.4/10 Exceptional! (864 reviews)
"Rooms were clean and comfortable ,staff was pleasant. Love the Manchester such a beautiful town."
Reviewed on 27 Aug 2026
On The River Inn
1653 West Woodstock Road Woodstock VT
€235
8 Sept - 9 Sept
includes taxes & fees
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
Bonnie's Bundles Dolls
7.6/10 (4 reviews)
This historic Vermont studio showcased handcrafted cloth dolls with embroidered faces and calico clothing. Visitors treasured personal interactions with artist Bonnie Watters and stories behind her creations.
DaVallia Art & Accents
10.0/10 (2 reviews)
This Vermont art haven showcases fine local art and handcrafted furniture in thoughtfully designed spaces. Browse both the Art Boutique and 39 North Gallery to experience indoor exhibits and outdoor sculpture gardens.
What to do in Chester
Colonial Flintlock Musket Experience
€111
per adult
100% of travellers recommend
Frequently asked questions
How much does a Chester holiday package cost?
You can grab a holiday package to this destination from €577 on Expedia. However, how much your holiday to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
If you'd like to snag a cheap Chester holiday package, consider planning a trip in March, May and June. You'll generally find better rates on accommodation and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Chester?
Usually, a handful of days is enough to see the major sights during your Chester holiday. However, if you want to have more time to chill out or take day trips, consider extending your itinerary.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most affordable 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 holiday as a package?
You can enjoy significant savings on your Chester escape by booking a customised holiday package. Click on the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Chester?
If you have your Chester travel dates finalized, book early to score some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Chester?
- Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the activities available will also help you decide when to visit Chester.
- Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodation will probably be the biggest expense during your trip to Chester.
- Decide how long to go for: Now that you're more familiar with Chester, you can work out the right length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customised Chester holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
