Title: Chester Center Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $614 Expedia.ca [Hotels in Chester Center](https://expedia.ca/Chester-Center-Chester-Hotels.0-n553248635976479536-0.Travel-Guide-Filter-Hotels)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d183058.Travel-Guide-Flights)[Chester Center Car Rentals](https://expedia.ca/Car-Rentals-In-Chester-Center.d553248635976479536.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester Center 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 Center Price found within the past 48 hours. Click for updated prices. ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/5cb2e3e0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pier Blue Inn Old Saybrook - Essex Saybrook Manor CA $614 per person May 15 - May 18 found 1 day ago Roundtrip flight included Toronto (YYZ) to New Haven (HVN) 8/10 Very Good! (1,004 reviews) Room could have been cleaner. The floor was dirty. The room also looked worn and in need of updating. The tub faucet dripped constantly, but the shower was nice. Staff was friendly. I was surprised they don’t offer daily housekeeping. Bed was comfortable. It was great that the room had a microwave and a fridge. It was not warm and inviting at all. Definitely wouldn’t stay more than one night. Reviewed on Mar 30, 2026 ![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 $2,654 per person Jun 8 - Jun 13 found 13 hours ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) No reviews ![The Surfside Hotel](https://images.trvl-media.com/lodging/91000000/90180000/90178600/90178584/44f176e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Surfside Hotel Lordship CA $963 per person Jun 2 - Jun 5 found 12 hours ago Roundtrip flight included Calgary (YYC) to New Haven (HVN) 9.4/10 Exceptional! (179 reviews) Lovely stay on the beach! Reviewed on Mar 26, 2026 ![James Pharmacy Bed & Breakfast](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### James Pharmacy Bed & Breakfast Old Saybrook Center CA $966 per person May 15 - May 18 found 1 day ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) 9/10 Wonderful! (23 reviews) Room was pleasant and clean, although small. Bathroom fixtures all new and very clean and functional. Firm bed, which I appreciated. The stairs are steep though there is a firm railing. I didn't realize that we would get a breakfast voucher as opposed to a true B&B experience. The restaurant provided was friendly and the food all looked great but unfortunately didn't have much flavor. The Paperback Cafe nearby had tastier choices. Make sure that you get their email about how to get in because there is no one on site and when we arrived after dark, the front of the building wasn't lit because the entry is in the back. On our first morning, we got a text about our credit card payment not going through. The owner and manager were both responsive but given that they weren't on site, a friendlier tone (i.e., assuming that there might've been a mistake in their information, which there was!) would've been appreciated. It's a lovely place in an excellent location but perhaps slightly expensive given that they are not providing a full B&B experience. Reviewed on Oct 6, 2025 ![Holiday Inn Express Branford-New Haven by IHG](https://images.trvl-media.com/lodging/1000000/130000/124400/124313/908bc53f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Branford-New Haven by IHG CA $995 per person May 21 - May 25 found 14 hours ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) 8.8/10 Excellent! (1,002 reviews) Excellent hotel. Very clean, convenient and the staff is just amazing. Helpful and courteous. Definitely will stay there again Reviewed on Mar 29, 2026 ## Chester Center Hotel Deals ![Hyatt Place Uncasville - Casino Area](https://images.trvl-media.com/lodging/3000000/2600000/2593900/2593874/a4b45014_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 $136 CA $157 total Apr 14 - Apr 15 includes taxes & fees 9.2/10 Wonderful! (2,663 reviews) I was very surprised at the upkeep off the property and room, it was poor condition. Furniture of the room was not appealing at all, heavily damaged tables, the condition of the bathroom tub was horrible and looked dirty, I barely wanted to shower. There was hair that did not even belong to me on ... Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=2593874&PinnedHotelID=2593874&HadPinnedHotel=true®ionId=553248635976479536) ![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/3f0d6a31_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel 6 New Haven - Branford, CT 320 E Main St Branford CT Fully refundable CA $99 CA $115 total Apr 6 - Apr 7 includes taxes & fees 7.2/10 Good! (1,010 reviews) Man checking me in said it was policy to copy ID when I said I didn’t like that and didn’t want him to. He showed me all the copies of everyone else’s IDs and said I had to. I think it’s poor business practice, especially when someone tells you they’re uncomfortable with it. No other hotels did this. ... Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=50320&PinnedHotelID=50320&HadPinnedHotel=true®ionId=553248635976479536) ![Mohegan Sun](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/37130fc3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Mohegan Sun 1 Mohegan Sun Boulevard Montville CT 9.2/10 Wonderful! (2,043 reviews) Clean room, very nice staff Reviewed on Mar 30, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=894248&PinnedHotelID=894248&HadPinnedHotel=true®ionId=553248635976479536) [](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=894248&PinnedHotelID=894248&HadPinnedHotel=true®ionId=553248635976479536) [See all 940 properties in Chester Center](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F04%2F2026&endDate=03%2F04%2F2026®ionId=553248635976479536) 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 Center vacation package cost? ### How do I get a cheap travel package to Chester Center? ### Where should I stay in Chester Center? ### What are the top hotels in Chester Center? ### How far in advance should I book my Chester Center vacation? ### What does an Expedia Chester Center travel package include? ### What should I know before booking a Chester Center travel package? ### Can I choose my airline with a Chester Center Expedia vacation package? ### If I'm not able to travel, can I cancel my Chester Center vacation package? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.