Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Chester Hotel Deals
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is CA $192 per night from Mar 9 to Mar 10
CA $192
CA $219 total
Mar 9 - Mar 10
includes taxes & fees
8.8/10 Excellent! (970 reviews)
Clean room! Great food!
Reviewed on Jan 30, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is CA $423 per night from Feb 22 to Feb 23
CA $423
CA $525 total
Feb 22 - Feb 23
includes taxes & fees
9.2/10 Wonderful! (562 reviews)
Excellent hotel, staff well trained.
Reviewed on Jan 21, 2026
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
7.2/10 Good! (594 reviews)
.
Reviewed on Feb 2, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
