Title: Chester Depot Vacation Packages 2026 from $696 | Expedia.com [Hotels in Chester Depot](https://expedia.com/Chester-Depot-Chester-Hotels.0-n553248635976384383-0.Travel-Guide-Filter-Hotels)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d89014.Travel-Guide-Flights)[Car Rentals in Chester Depot](https://expedia.com/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 Vacations from $696 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## Your Chester Depot Vacation Make planning your travels easy by creating a vacation package to Chester Depot. We'll handle the specifics, so you can concentrate on discovering everything this neighborhood has to offer. If you're in the mood to sightsee, no trip to Chester Depot is complete without a visit to nearby [DaVallia Art & Accents](https://www.expedia.com/DaVallia-Art-Accents-Chester-Depot.d553248621532666916.Vacation-Attraction). Don't just wish for it — take action! Lock in your perfect Chester Depot vacation with Expedia and enjoy traveling your way. ## The Latest Chester Depot Vacation Packages Price found within the past 48 hours. Click for updated prices. ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Covered Bridge Inn $696 per person Apr 10 - Apr 13 found 1 day ago Roundtrip flight included Fort Myers (RSW) to Springfield (VSF) 7.6/10 Good! (1,002 reviews) Easy check in and good parking Reviewed on Jan 9, 2026 ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shire Woodstock $839 per person Mar 17 - Mar 22 found 1 day ago Roundtrip flight included Tampa (TPA) to Springfield (VSF) 8.8/10 Excellent! (881 reviews) Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire! Reviewed on Jan 30, 2026 ![Stone Hearth Inn and Eatery](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/f814b3d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Stone Hearth Inn and Eatery $895 per person Apr 10 - Apr 13 found 1 day ago Roundtrip flight included Fort Myers (RSW) to Springfield (VSF) 9.2/10 Wonderful! (106 reviews) So great all around! Reviewed on Jan 4, 2026 ![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 $1,367 per person Mar 17 - Mar 22 found 1 day ago Roundtrip flight included Tampa (TPA) to Springfield (VSF) 9.2/10 Wonderful! (549 reviews) Excellent hotel, staff well trained. Reviewed on Jan 21, 2026 ![Mountain Lodge at Okemo](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417011/5263ccb3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mountain Lodge at Okemo Clock Tower Base Area $1,332 per person Mar 17 - Mar 22 found 1 day ago Roundtrip flight included Tampa (TPA) to Springfield (VSF) 8/10 Very Good! (219 reviews) We really enjoyed our stay at the Mountain Lodge at Okemo, it was clean and our room was newly renovated and very cute. Would definitely recommend!! Reviewed on Oct 6, 2025 ## 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 $129 nightly $141 total Mar 1 - Mar 2 Total with taxes and fees 8/10 Very Good! (414 reviews) The staff was great from the minute we checked in to the great service we received at the tavern Reviewed on Feb 8, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%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 $142 nightly $154 total Mar 3 - Mar 4 Total with taxes and fees 8.8/10 Excellent! (975 reviews) Nice & helpful staff, great location, clean Reviewed on Feb 10, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F3%2F2026&endDate=3%2F4%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 $154 nightly $168 total Mar 2 - Mar 3 Total with taxes and 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.com/Hotel-Search?startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&selected=425171&PinnedHotelID=425171&HadPinnedHotel=true®ionId=553248635976384383) [See all 1,635 properties in Chester Depot](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F12%2F2026&endDate=2%2F13%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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ### Discover the most popular places to visit in Chester Depot #### 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. [](https://expedia.com/Bonnies-Bundles-Dolls-Chester-Depot.d553248621561865050.Vacation-Attraction) #### 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. [](https://expedia.com/DaVallia-Art-Accents-Chester-Depot.d553248621532666916.Vacation-Attraction) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.