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 ₩221,053 per night from Aug 3 to Aug 4
₩221,053
₩240,948 total
Aug 3 - Aug 4
includes taxes & fees
8/10 Very Good! (369 reviews)
"It’s not like anyplace I have stayed before. It’s so homey and very comfortable. The staff is very friendly and it’s clean as a whistle."

Reviewed on Jul 25, 2025

Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is ₩624,231 per night from Aug 17 to Aug 18
₩624,231
₩747,826 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (528 reviews)
"Really enjoyed our stay."

Reviewed on Jul 18, 2025

Woodstock Inn & Resort
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is ₩136,385 per night from Aug 3 to Aug 4
₩136,385
₩150,024 total
Aug 3 - Aug 4
includes taxes & fees
6.6/10 (1,001 reviews)
"Always a pleasure to stay at the Colonial"

Reviewed on Jul 28, 2025

Colonial Motel And Spa
See all 2,967 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 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.