Title: Chester Depot Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,740 Expedia.ca [Hotels in Chester Depot](https://expedia.ca/Chester-Depot-Chester-Hotels.0-n553248635976384383-0.Travel-Guide-Filter-Hotels)[Chester Depot Car Rentals](https://expedia.ca/Car-Rentals-In-Chester-Depot.d553248635976384383.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248635976384383/172b7db7-b524-4c32-84cc-eb436772ed39.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester Depot Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Holiday Package Deals in Chester Depot Price found within the past 48 hours. Click for updated prices. ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Woodstock Inn & Resort CA $1,740 per person Mar 18 - Mar 22 found 23 hours ago Roundtrip non-stop flight included Toronto (YTO) to Springfield (VSF) 9.2/10 Wonderful! (549 reviews) Excellent hotel, staff well trained. Reviewed on Jan 21, 2026 ## Chester Depot Hotel Deals ![Fullerton Inn](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fullerton Inn 40 The Common Chester VT Fully refundableReserve now, pay when you stay CA $176 CA $191 total Mar 1 - Mar 2 includes taxes & fees 8/10 Very Good! (416 reviews) Friendliness, ease of checkin and iut Reviewed on Feb 14, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=15845368&PinnedHotelID=15845368&HadPinnedHotel=true®ionId=553248635976384383) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pointe at Castle Hill Resort 2940 State Route 103 Cavendish VT CA $186 CA $213 total Mar 8 - Mar 9 includes taxes & fees 8.8/10 Excellent! (975 reviews) Nice & helpful staff, great location, clean Reviewed on Feb 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=1823093&PinnedHotelID=1823093&HadPinnedHotel=true®ionId=553248635976384383) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 485 Hotel Road Brownsville VT Fully refundable CA $176 CA $214 total Mar 9 - Mar 10 includes taxes & fees 8.8/10 Excellent! (793 reviews) Staff are so friendly ,great place very clean rooms a lot of activities Reviewed on Feb 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=425171&PinnedHotelID=425171&HadPinnedHotel=true®ionId=553248635976384383) [See all 1,640 properties in Chester Depot](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F02%2F2026&endDate=18%2F02%2F2026®ionId=553248635976384383) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Chester Depot vacation package cost? ### How do I get a cheap travel package to Chester Depot? ### Where should I stay in Chester Depot? ### What are the top hotels in Chester Depot? ### How far in advance should I book my Chester Depot vacation? ### What does an Expedia Chester Depot travel package include? ### What should I know before booking a Chester Depot travel package? ### Can I choose my airline with a Chester Depot Expedia vacation package? ### If I'm not able to travel, can I cancel my Chester Depot vacation package? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.