Title: Chester Vacation Packages & Trips 2026 from CA $2,679 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d183058.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d183058.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d183058.Travel-Guide-Flights)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d183058.Car-Rental-Guide) ![](https://images.trvl-media.com/place/183058/f457b867-7f08-4489-b983-3426d68ada3d.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 The best way to experience this vibrant city is with a custom-made Chester vacation package. Stay in the neighborhood of Essex Village, which is good for walking, hiking and views or choose someplace else — our packages are all about you. [Essex Steam Train](https://www.expedia.ca/Essex-Steam-Train-Essex.d6171206.Vacation-Attraction), [Goodspeed Opera House](https://www.expedia.ca/Goodspeed-Opera-House-East-Haddam.d6089799.Vacation-Attraction) and [Essex Island Marina](https://www.expedia.ca/Essex-Island-Marina-Essex.d6326375.Vacation-Attraction) are just some of the many sights you'll want to check out during your trip to Chester. Check out Expedia's extensive range of travel options and begin planning your perfect vacation to Chester now. ## Top Chester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Beechmont - Perfect for Family Retreat!](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/6e17e1d7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beechmont - Perfect for Family Retreat! North End CA $2,679 per person Apr 25 - Apr 29 found 19 hours ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) No reviews ## Ready to book your vacation to Chester? Choose your dates ## Chester Hotel Deals ![Hyatt Place Uncasville - Casino Area](https://images.trvl-media.com/lodging/3000000/2600000/2593900/2593874/46d6d7fc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place Uncasville - Casino Area 2049 Norwich Montville CT Fully refundableReserve now, pay when you stay CA $127 CA $146 total Feb 25 - Feb 26 includes taxes & fees 9/10 Wonderful! (2,613 reviews) good Reviewed on Feb 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&selected=2593874&PinnedHotelID=2593874&HadPinnedHotel=true®ionId=183058) ![Mohegan Sun](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/60dec0f3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Mohegan Sun 1 Mohegan Sun Boulevard Montville CT CA $296 CA $375 total Feb 25 - Feb 26 includes taxes & fees 9/10 Wonderful! (2,080 reviews) The room was fine but the thermostat was had to use. iI did feel cool in the room and it said it was 76 and it felt like 66. Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&selected=894248&PinnedHotelID=894248&HadPinnedHotel=true®ionId=183058) ![Holiday Inn Norwich by IHG](https://images.trvl-media.com/lodging/1000000/10000/1500/1450/d9b5e4b8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Norwich by IHG 10 Laura Blvd Norwich CT Fully refundable CA $133 CA $153 total Feb 15 - Feb 16 includes taxes & fees 7.4/10 Good! (1,003 reviews) Clean, nice amenities, quiet Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=1450&PinnedHotelID=1450&HadPinnedHotel=true®ionId=183058) [See all 1,073 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=183058) 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) ## 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. ![](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