Chester Vacations

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Find the Best Chester Vacation Packages

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 NT$4,196 per night from Apr 26 to Apr 27
NT$4,196
NT$4,574 total
includes taxes & fees
Apr 26 - Apr 27
8/10 Very Good! (347 reviews)
"Excellent service to help resolve reservation mix up. Small but serviceable room. Very limited breakfast. On premises restaurant was excellent for dinner"

Reviewed on 2025/3/22

Fullerton Inn
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NT$9,726 per night from May 26 to May 27
NT$9,726
NT$12,130 total
includes taxes & fees
May 26 - May 27
9.2/10 Wonderful! (512 reviews)
"The Woodstock Inn is beautiful. Nice having access to the Athletic Club and a shuttle."

Reviewed on 2025/4/22

Woodstock Inn & Resort
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 NT$4,195 per night from Apr 27 to Apr 28
NT$4,195
NT$5,015 total
includes taxes & fees
Apr 27 - Apr 28
8.8/10 Excellent! (692 reviews)
Great value
"Beautiful property at Mt. Asutney. Tons of space. Nice restaurant. Looks as good in real lfe as it does in the pictures."

Reviewed on 2025/4/21

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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.

Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this destination on Expedia. However, how much your vacation 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 vacation package, consider planning a trip in March, May and June. You’ll generally find better rates on accommodations 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 vacation. 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,” “Traveler 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 vacation as a package?
You can enjoy significant savings on your Chester escape by booking a customized vacation 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 vacation 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 traveling on a whim.
How to plan a trip to Chester?

  1. 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.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodations will probably be the biggest expense during your trip to Chester.
  3. 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.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Chester vacation package.

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