Chester Vacations from $640
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Your Chester Vacation
Excellent adventures await when you reserve a Chester vacation package. Whether you're a history buff, art enthusiast or just a traveler who loves to experience new places, there's something for everyone in this lively city. Need some ideas on what to see or do first during your trip to Chester? Don't miss leading attractions like DaVallia Art & Accents. Your ultimate Chester vacation is just clicks away. Search flights, accommodations and more on Expedia for a trip that's tailored to suit your travel style.
The Latest Chester vacation packages
Price found within the past 48 hours. Click for updated prices.
Discover the most popular places to visit in Chester
DaVallia Art & Accents
Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.
Bonnie's Bundles Dolls
Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views, or seek out its ski slopes.
Chester Hotel Deals
Fullerton Inn
40 The Common, Chester, VT
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $162 total per night from Jul 3 to Jul 4
$162 total
Jul 3 - Jul 4
Total includes taxes and fees
8/10 Very Good! (362 reviews)
"Very cute hotel, friendly staff, charming location. The bed was a little saggy, but otherwise my room was great."
Reviewed on Jun 21, 2025
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 Feb 24, 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$469 nightly
The price is $516 total per night from Jul 6 to Jul 7
$516 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (521 reviews)
"Relaxing"
Reviewed on Jun 25, 2025
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.
Find the Best Chester Vacation Packages
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Lebanon Municipal Airport (LEB) |
Population | 3,000 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Weston Playhouse, Weston Priory and Fox Run Golf Course |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.