Title: Chesterfield Vacation Packages & Trips 2026 from CA $989 | Expedia.ca [Hotels in Chesterfield](https://expedia.ca/Chesterfield-Hotels.d6052872.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.ca/Chesterfield-Vacation-Rentals.d6052872.Travel-Guide-VacationRentals)[Chesterfield Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterfield.d6052872.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6052872/fc91b262-156e-463c-9b9c-bb779209c85d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chesterfield 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 Chesterfield Vacation When a city escape is calling, answer it with a vacation package to Chesterfield. With all your travel arrangements in order before you go, all you need to do here is focus on having the time of your life. Fill your free time with tours of [Spofford Lake](https://www.expedia.ca/Spofford-Lake-Spofford.d6265753.Vacation-Attraction), [Asbury United Methodist Church](https://www.expedia.ca/Asbury-United-Methodist-Church-Chesterfield.d6265749.Vacation-Attraction) and [Madame Sherris Castle Ruins](https://www.expedia.ca/Madame-Sherris-Castle-Ruins-West-Chesterfield.d6273836.Vacation-Attraction), some of the top attractions you really should see during your trip to Chesterfield. Whoever you're taking a break with and whatever the size of your budget, your ultimate Chesterfield vacation is just a few clicks away with Expedia. ## Top Chesterfield Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Green Granite Inn, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/2000000/1220000/1220000/1219930/84e2004b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Green Granite Inn, an Ascend Collection Hotel Settlers Green CA $989 per person Apr 3 - Apr 6 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Manchester (MHT) 6.8/10 (1,234 reviews) Nice stay at the Green Granite. Super close to all the action.The hot tub was perfect after a day of sub zero shredding the gnar. The toilet was fierce! It could easily eliminate an entire loaf of bologna. After the flush, it made a mega thump as if to open a portal to another dimension. Emily checked us in and couldn't have been nicer. She also tended a mean fire in the lobby! Reviewed on Feb 8, 2026 ![The Inn at Thorn Hill & Spa](https://images.trvl-media.com/lodging/8000000/7480000/7475900/7475891/2030cf4f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Thorn Hill & Spa CA $1,134 per person Apr 3 - Apr 6 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Manchester (MHT) 9.8/10 Exceptional! (1,001 reviews) Our visit to the Thorn Hill INn couldn't have been better. Our room was meticulous and comfortable. The view from the room was an expansive view of the mountains. We dined at the inn both nights and our meals were top notch. James and Ed our bartender were pleasant and the mixed drink James made me was outstanding. The staff was attentive and friendly. We will be back soon! Reviewed on Jan 29, 2026 ![Eastern Slope Inn Resort](https://images.trvl-media.com/lodging/1000000/900000/893400/893382/577db6c4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eastern Slope Inn Resort North Conway Village CA $1,218 per person Apr 3 - Apr 6 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Manchester (MHT) 8.8/10 Excellent! (444 reviews) Great place great atmosphere Reviewed on Jan 6, 2026 ![Cranmore Mountain Lodge Bed & Breakfast](https://images.trvl-media.com/lodging/1000000/180000/179500/179410/a41f71e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cranmore Mountain Lodge Bed & Breakfast Kearsarge CA $1,157 per person Apr 3 - Apr 6 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Manchester (MHT) 8.8/10 Excellent! (244 reviews) everything was great Reviewed on Jan 1, 2026 ![Attitash Mountain Village](https://images.trvl-media.com/lodging/1000000/900000/893400/893392/991e7096_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Attitash Mountain Village CA $1,087 per person Apr 3 - Apr 6 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Manchester (MHT) 8.6/10 Excellent! (542 reviews) very comfortable for attitash skiing Reviewed on Jan 20, 2026 ## Ready to book your vacation to Chesterfield? Choose your dates ## Chesterfield Hotel Deals ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Brattleboro 1378 Putney Road Brattleboro VT Fully refundableReserve now, pay when you stay CA $156 CA $171 total Mar 1 - Mar 2 includes taxes & fees 8.2/10 Very Good! (940 reviews) Recently renovated room Reviewed on Jan 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=1158047&PinnedHotelID=1158047&HadPinnedHotel=true®ionId=6052872) ![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Brattleboro I-91 1186 Putney Road Brattleboro VT Fully refundableReserve now, pay when you stay CA $168 CA $185 total Mar 5 - Mar 6 includes taxes & fees 8.4/10 Very Good! (760 reviews) Nice location… clean room! Breakfast was not appetizing… Reviewed on Jan 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F03%2F2026&endDate=06%2F03%2F2026&selected=8784377&PinnedHotelID=8784377&HadPinnedHotel=true®ionId=6052872) ![The White House Inn](https://images.trvl-media.com/lodging/3000000/2940000/2937400/2937372/fe9c2db1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The White House Inn 178 Route 9 East Wilmington VT CA $214 CA $236 total Mar 11 - Mar 12 includes taxes & fees 9/10 Wonderful! (283 reviews) It was quiet and beautiful. Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=2937372&PinnedHotelID=2937372&HadPinnedHotel=true®ionId=6052872) [See all 535 properties in Chesterfield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F02%2F2026&endDate=11%2F02%2F2026®ionId=6052872) 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