Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NZ$616 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Chester Holiday

Our pick of the best 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 NZ$255 per night from 7 Sept to 8 Sept
NZ$255
7 Sept - 8 Sept
includes taxes & fees
8/10 Very Good! (370 reviews)
Great Inn in a quaint town.
"A wonderful little Inn with such a pleasant owner and just a great vibe there. Would absolutely recommend for a summer or winter stay. Can imagine it is beautiful in the winter."

Reviewed on 3 Aug. 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

Get rates
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 NZ$832 per night from 2 Sept to 3 Sept
NZ$832
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (530 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on 30 Jul. 2025

Woodstock Inn & Resort
See all 2,972 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.