Chester Holidays

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Top hotels in Chester

Fullerton Inn
Fullerton Inn
2.5 out of 5
40 The Common, Chester, VT
Fully refundableReserve now, pay when you stay
The price is €140 per night from 29 Jun to 30 Jun
€140
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (361 reviews)
"Very cute hotel, friendly staff, charming location. The bed was a little saggy, but otherwise my room was great."

Reviewed on 21 Jun 2025

Fullerton Inn
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Chester
9.8/10 Exceptional! (23 reviews)
Hidden gem!
"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"

Reviewed on 24 Feb 2025

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Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is €445 per night from 6 Jul to 7 Jul
€445
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."

Reviewed on 20 Jun 2025

Woodstock Inn & Resort
See all 2,982 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.

Frequently asked questions

How much does a Chester holiday package cost?
You can grab a holiday package to this destination 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?

  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 accommodation 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 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.