Name: Pointe at Castle Hill Resort
Price range: CA $185
Rating: 8.8

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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

40 The Common Chester VT

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

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

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

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT

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

See all 3,116 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.