Title: Visit Winchester: Best of Winchester Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000447144.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000447144.Destination-Travel-Guides) # Winchester ## Travel Guide ![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![covered bridge in winter -Ashuelot Covered Bridge, Winchester, New Hampshire ](https://images.trvl-media.com/place/3000447144/a4923834-5259-4cab-a093-d05a4fb5d95d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Black and white Lattice work detail on The Ashuelot Covered Bridge crosses the Ashuelot River and Bolton Road in Winchester New Hampshire](https://images.trvl-media.com/place/3000447144/e01c36c6-26e4-4e34-acfd-f05d6b9e1aec.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Winchester](https://images.trvl-media.com/place/3000447144/529ffd18-db0c-4d9e-8844-fe610e44574f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Winchester Things to do - Winchester Hotel Deals - Vacation Rentals in Winchester ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/ad889baf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Colonial Hotel 625 Betty Spring Road Gardner MA CA $200 CA $223 total Apr 12 - Apr 13 includes taxes & fees Book a stay at this business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ... 8.8/10 Excellent! (1,004 reviews) Bathroom should have a safety grab bar in the shower as well as hooks for towels. Reviewed on Apr 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=40458&PinnedHotelID=40458&HadPinnedHotel=true®ionId=3000447144) ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Colonial Motel And Spa 889 Putney Rd Brattleboro VT CA $127 CA $139 total Apr 16 - Apr 17 includes taxes & fees Book a stay at this spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ... 6.8/10 (1,002 reviews) Older motel style not fancy. Good hot tub in pool area. Ok for overnight on a budget. Reviewed on Apr 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=1070729&PinnedHotelID=1070729&HadPinnedHotel=true®ionId=3000447144) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Brattleboro 1378 Putney Road Brattleboro VT CA $181 CA $199 total Apr 22 - Apr 23 includes taxes & fees Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ... 8.2/10 Very Good! (956 reviews) Nice Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=1158047&PinnedHotelID=1158047&HadPinnedHotel=true®ionId=3000447144) [See all 470 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=09%2F04%2F2026&endDate=10%2F04%2F2026®ionId=3000447144) 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. ![Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly](https://images.trvl-media.com/lodging/92000000/91080000/91076100/91076053/9fe7ea33_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly Wilmington VT Stay at this cottage in Wilmington. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Lake Raponda and Molly Stark State Park ... 8.6/10 Excellent! (66 reviews) Cozy and peaceful, just with they had turned the heat up before u got there. It was like 45-50 when I arrived and had to figure out the heating and wait for it to warm up for the first few hours. Reviewed on Feb 19, 2026 [](https://expedia.ca/Wilmington-Hotels-Cottage-In-The-Woods-With-A-Firepit.h91076053.Hotel-Information) ![Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min](https://images.trvl-media.com/lodging/84000000/83630000/83628700/83628695/3c563e55_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min Rindge NH Stay at this cottage in Rindge. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pearly Lake and Jowder's Cove Beach are located ... 10/10 Exceptional! (17 reviews) This place was great. We stayed a week in winter and it was super pretty and was a great house. We loved the fireplace and hot tub and even did some ice fishing. House was super clean and we really appreciated that. Would definitely come back! Reviewed on Jan 2, 2026 [](https://expedia.ca/Rindge-Hotels-Beautiful-Waterfront-Cottage-With-A-HOT-TUB-For-Your-Family-Getaway.h83628695.Hotel-Information) ![Lovely 2nd Floor Apartment](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/01ff54d0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lovely 2nd Floor Apartment Greenfield MA Book a stay at this family-friendly vacation home in Greenfield. Enjoy a garden, an in-room coffeemaker, and housekeeping. Popular attractions Poet's Seat Tower ... 10/10 Exceptional! (52 reviews) Beautiful, thoughtful space on a gorgeous piece of property. Reviewed on Apr 1, 2026 [](https://expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information) [See all properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=3000447144&sort=VACATION_RENTAL) 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. ## Check Winchester hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000447144&startDate=2026-04-08&endDate=2026-04-09)[Apr 8 - Apr 9](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000447144&startDate=2026-04-08&endDate=2026-04-09) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000447144&startDate=2026-04-09&endDate=2026-04-10)[Apr 9 - Apr 10](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000447144&startDate=2026-04-09&endDate=2026-04-10) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000447144&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026)[Apr 10 - Apr 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000447144&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000447144&startDate=17%2F04%2F2026&endDate=19%2F04%2F2026)[Apr 17 - Apr 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000447144&startDate=17%2F04%2F2026&endDate=19%2F04%2F2026) ### Popular places to visit #### Winchester Speedpark You can take time to visit Winchester Speedpark during your travels to Winchester. While you're in the area, stroll along the lakeside. [](https://expedia.ca/Winchester-Speedpark-Winchester.d934550877316976640.Vacation-Attraction) #### Cass Pond Commune with nature and explore the great outdoors at Cass Pond during your travels in Richmond. [](https://expedia.ca/Cass-Pond-Winchester.d934550841938022400.Vacation-Attraction) #### New England Sweetwater Farm & Distillery You can take time to visit New England Sweetwater Farm & Distillery during your travels to Winchester. While you're in the area, stroll along the lakeside. [](https://expedia.ca/New-England-Sweetwater-Farm-Distillery-Winchester.d934551452230144000.Vacation-Attraction) #### Richmond Town Hall After visiting Richmond Town Hall, make a plan to see the other sights and activities in Richmond. [](https://expedia.ca/Richmond-Town-Hall-Winchester.d934551059299713024.Vacation-Attraction) #### Loring Field Explore the great outdoors at Loring Field, a lovely green space in Winchester. While you're in the area, stroll along the lakeside. [](https://expedia.ca/Loring-Field-Winchester.d934551530481532928.Vacation-Attraction) #### Richmond Wildlife Manangement Area Explore the great outdoors at Richmond Wildlife Manangement Area, a lovely green space in Richmond. [](https://expedia.ca/Richmond-Wildlife-Manangement-Area-Winchester.d934551484100616192.Vacation-Attraction) - Cities near Winchester - Places of interest - [Green Mountain National Forest ](https://expedia.ca/Green-Mountain-National-Forest-Vermont.d6115904.Vacation-Attraction) - [Landmark College ](https://expedia.ca/Landmark-College-Putney.d553248635937215663.Vacation-Attraction) - [Monadnock State Park ](https://expedia.ca/Monadnock-State-Park-Jaffrey.d553248621532666842.Vacation-Attraction) ![](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