Chester Vacations from $255
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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.
Deerfield Valley Inn
Save 100% on your flight
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
9.6/10 Exceptional! (54 reviews)
This is such a charming, historic New England bed and breakfast. The quintessential Vermont experience right in the heart of the quaint village of West Dover. The Innkeeper knows all the people & places around. Homemade breakfast options are delicious, I had the local blueerry waffles. The Blueberry Festival parade passed right in front of the inn. I drank the Inn's coffee in the morning outside on their lawn, on one of the oversized stone seats around the firepit. There are books on the shelves and games in the living room. The Inn is in a perfect location, walking distance - with sidewalks - to multiple restaurants. And just 10 minutes to the town of Wilmington and the GORGEOUS water at Harriman Reservoir or Lake Raponda. There's 2 golf courses a few minutes away. And 2 ski mountains too! This place is super quiet, but close to whatever you might need. The Inn is filled with cozy furnishings, antiques, fireplaces, etc. Lovely lovely, so New England, so Vermont.
Reviewed on Aug 8, 2025
Chalet 239
Save 100% on your flight
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
9.4/10 Exceptional! (70 reviews)
Teh staff were friendly and helpful. Immediately upon booking I received a text message from the staff letting me know someone was there to help with any questions. checking in was easy and the hotel was very clean. The room, beds and bathroom were all clean and well kept.
The free breakfast was a plus.
Reviewed on Aug 12, 2025
Mount Snow Lodging
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8/10 Very Good! (22 reviews)
The room hotel was very nice. The parking lot was very icy and snowy and the indoor hot tub had a lot of chlorine odor coming from it so we couldn't use that because we had a baby and it was too much smelling like chlorine. Great location though to go skiing
Reviewed on Apr 9, 2025
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
$139 nightly
The price is $152 total per night from Sep 1 to Sep 2
$152 total
Sep 1 - Sep 2
Total includes taxes and fees
8/10 Very Good! (371 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 Aug 3, 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
$449 nightly
The price is $494 total per night from Sep 1 to Sep 2
$494 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (531 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 Jul 30, 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.
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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.