Title: Chester Vacation Packages & Trips 2026 from CA $907 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Things to do in Chester](https://expedia.ca/Things-To-Do-In-Chester.d89014.Travel-Guide-Activities)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester 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 #### 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](https://www.expedia.ca/DaVallia-Art-Accents-Chester-Depot.d553248621532666916.Vacation-Attraction). 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. ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Latchis Hotel CA $907 per person May 21 - May 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Springfield (VSF) 8.6/10 Excellent! (853 reviews) If you love retro/vintage/history/ quiet and pet friendly this place is wonderful for a short stay and lowkey weekend. So many cool local businesses and delicious food. We went for a show at the stone church- walking distance from hotel! And everything we could have needed was easily accessible. They have a bar downstairs and a movie theatre in the hotel! All rooms have record players and vinyls to play with more available. Big rooms. “Dated” but it’s keeping with the retro style- very clean and neat. Only negatives were the parking lot (really small but we got a spot! There’s plenty of on street parking and a nearby parking garage as well). Staff was so friendly and helpful! This would be a great “staycation” or mom night away as well. Stop at some of the amazing thrift/vintage/2nd hand stores for books, music, clothes and more. If you’re a crafter, Bobbins’and Skeins and Beadnik are great places to take a look at. I’d definitely come back! Reviewed on Mar 30, 2026 ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/c3cb22fe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shire Woodstock CA $1,021 per person May 21 - May 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Springfield (VSF) 8.8/10 Excellent! (914 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 ![Grand Summit Resort, A Vail Resorts Property](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/7d1f7aea_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Summit Resort, A Vail Resorts Property CA $908 per person May 21 - May 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Springfield (VSF) 8.6/10 Excellent! (262 reviews) Great place to stay for ski trip Reviewed on Mar 14, 2026 ![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/50bc8764_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG CA $1,342 per person May 21 - May 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Springfield (VSF) 8.8/10 Excellent! (1,002 reviews) Staff was very courteous. The hot soup in the lobby was a nice touch! Loved the breakfast selections. Reviewed on Mar 1, 2026 ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn Brattleboro CA $1,004 per person May 21 - May 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Springfield (VSF) 8.2/10 Very Good! (950 reviews) I wish I could have stayed longer. Very nice hotel Reviewed on Mar 10, 2026 ## Ready to book your vacation to Chester? Choose your dates ## Chester 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 $179 CA $195 total Apr 16 - Apr 17 includes taxes & fees 8/10 Very Good! (424 reviews) Yes, little guests easy parking spaces. Restaurant staff were pleasant. Heat didn’t appear until 11PM. A tad chilly. Room was clean. Reviewed on Mar 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=15845368&PinnedHotelID=15845368&HadPinnedHotel=true®ionId=89014) ![Stone Hearth Inn and Eatery](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Stone Hearth Inn and Eatery 698 VT-11 Chester VT Fully refundableReserve now, pay when you stay CA $287 CA $313 total Apr 2 - Apr 3 includes taxes & fees 9.2/10 Wonderful! (117 reviews) Fantastic breakfast in this quaint inn. Right in the road so very easy to find. Wonderful meal in the attached restaurant. Friendly staff. Easy parking. Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%2F04%2F2026&selected=87486236&PinnedHotelID=87486236&HadPinnedHotel=true®ionId=89014) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pointe at Castle Hill Resort 2940 State Route 103 Cavendish VT CA $200 CA $228 total Apr 14 - Apr 15 includes taxes & fees 8.8/10 Excellent! (1,008 reviews) Have stayed here many times. Close to town and Okemo. Very convenient. Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=1823093&PinnedHotelID=1823093&HadPinnedHotel=true®ionId=89014) [See all 3,120 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F04%2F2026&endDate=02%2F04%2F2026®ionId=89014) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app