Chester Vacation Packages

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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.

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Chester Hotel Deals

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
The price is CA $176 per night from May 12 to May 13
CA $176
CA $192 total
May 12 - May 13
includes taxes & fees
8.2/10 Very Good! (433 reviews)
The staff were incredible and the property have the perfect vibes for a ski trip. The food was great and everything was very clean and comfy.

Reviewed on Apr 16, 2026

Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $436 per night from May 25 to May 26
CA $436
CA $540 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (576 reviews)
Everything was excellent

Reviewed on May 5, 2026

Woodstock Inn & Resort
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
The price is CA $185 per night from May 27 to May 28
CA $185
CA $211 total
May 27 - May 28
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Staff was amazing. I didnt catch her name, but she was wonderful

Reviewed on May 3, 2026

Pointe at Castle Hill Resort
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.