Title: Winchester Apartment Rentals from CA $246 | 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) ![](https://mediaim.expedia.com/destination/2/ea42c861000f38e6206ed251ac7da597.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Donny Campos # Search Apartment Rentals in Winchester ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Apartments ![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/c9f7c522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/262afaed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/41130fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/27c20437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy apt in beautiful secluded spot 15 mins from Mt Snow Dover 10/10 Exceptional (4) "Catherine contacted me immediately that the studio I had rented was not available but that we could have the adjacent house instead. She moved heaven and earth to make sure we had a king bed ( which is what we wanted). She was very attentive and accommodating. " CA $119 CA $288 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/East-Dover-Hotels-Cozy-Apt-In-Beautiful-Secluded-Spot-15-Mins-From-Mt-Snow.h113155266.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/173c3a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/b0490e8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/b4e38c32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/9f760421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Whitingham & Mount Snow Area Village Apartment Whitingham 10/10 Exceptional (1) "This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home." CA $196 CA $427 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Jacksonville-Hotels-Lake-Whitingham-Mount-Snow-Area-Village-Garden-Apartment-2-BR.h108320042.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106850000/106848800/106848723/2e6ac870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/107000000/106850000/106848800/106848723/870206b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/107000000/106850000/106848800/106848723/5c7e01ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/107000000/106850000/106848800/106848723/32416b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious & Cozy Ground Floor 2/3 Bed private suite Shelburne Falls 10/10 Exceptional (3) "Great property and location for a visit to Shelburne Falls. " CA $223 CA $503 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Shelburne-Falls-Hotels-Spacious-Cozy-Ground-Floor-23-Bed-Private-Suite.h106848723.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/beaec720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/8c094e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/06a81bab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/57c0c927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town. Peterborough 9.8/10 Exceptional (25) "great location" CA $133 CA $251 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Peterborough-Hotels-Studio-Apt-With-Full-Kitchen-1-Minute-Stroll-Over-Picturesque-Bridge-Into-Town.h102238328.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/4d1d83e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/7a0cf170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/6767fc12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/721eacf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires Greenfield CA $115 CA $324 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Greenfield-Hotels-Charming-Country-Chic-1BR-In-Greenfield-King-Bed.h120530639.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/ec2105a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/1f82fc7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/4f40d5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/8031ab01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terrific 3-bedroom unit in charming Leverett with AC Leverett CA $280 CA $607 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Leverett-Hotels-Terrific-3-Bedroom-Unit-In-Charming-Leverett-With-AC.h120414848.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/e86ed09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rose wisteria 4 guests 2 bedrooms-full+queen beds Shelburne Falls CA $193 CA $364 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Shelburne-Falls-Hotels-Rose-Wisteria-4-Guests-2-Bedrooms-Fullqueen-Beds.h120039338.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28®ionId=3000447144&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Apartments.d3000447144-aaApartments.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Apartments.d3000447144-aaApartments.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Best Western Plus Keene Hotel](//images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "Was" [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Hampton Inn & Suites Greenfield](//images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg) ### Hampton Inn & Suites Greenfield 10/10 Excellent "Room was spacious and clean, breakfast had quite a few choices." [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "The staff was helpful and friendly. The breakfast was good with many choices available. The room was good and the bed was comfortable. My wife would have liked to have a hair dryer available." [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Excellent staff" [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](//images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 10/10 Excellent "Clean room" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Hampton Inn Brattleboro](//images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Staff was very helpful " [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Travelodge by Wyndham Brattleboro VT](//images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/19b6c01d_y.jpg) ### Travelodge by Wyndham Brattleboro VT 6/10 Okay "For the money during peep season it was ok. Otherwise it’s a low quality stay" [](https://expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.Hotel-Information) ![The Colonial Hotel](//images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "We always love staying at Colonial Inn when we visit family in the area. We informed the front desk concerning an issue with a stairwell door and it was fixed by end of day, on a Saturday!!" [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Riverhouse by Weekender (Formerly Jack Daniels Inn)](//images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/5d62062a_y.jpg) ### Riverhouse by Weekender (Formerly Jack Daniels Inn) 10/10 Excellent ".." [](https://expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information) ## Find out more about Winchester ## Winchester Apartments information | Number of reviews | 30 | | --- | --- | | Accommodation | 35 Apartments | | Lowest Price | CA $246 | | Highest Price | CA $607 | ## Frequently asked questions ### What's it like to stay at an apartment in Winchester? > You'll find 6 hotels and other accommodations in Winchester. Though there aren't many apartments, we can help you find accommodations with similar amenities. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. You can also search for similar property types like condos, vacation homes, or cottages. Why not take time to appreciate the lakeside during your visit? ### How do you know if an apartment is the right choice for you? > An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for solo travelers who want to stay in at night and plan out their next day, but also for families wanting the conveniences of home. ### What's a favorite apartment for a stay in Winchester? > Here are some of the top apartments in the area: [Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.](https://www.expedia.ca/Peterborough-Hotels-Studio-Apt-With-Full-Kitchen-1-Minute-Stroll-Over-Picturesque-Bridge-Into-Town.h102238328.Hotel-Information): Situated in Peterborough, 23.2 mi/37.4 km from the heart of Winchester. Includes free WiFi and Smart TVs. [Riverfront 2 Bedroom Unit 2](https://www.expedia.ca/Montague-Hotels-Riverfront-2-Bedroom-Unit-2.h90180457.Hotel-Information): Located 14.5 mi/23.3 km away in Montague. Amenities include Smart TVs. [Riverside Retreat – Cozy 2-Story Getaway!](https://www.expedia.ca/Montague-Hotels-Cozy-2-Bedroom-Unit-With-Private-Backyard.h90172818.Hotel-Information): 14.5 mi/23.3 km away in Montague. Free WiFi, private patios, and Smart TVs are included. ### What will the weather be like when I travel to Winchester? > Weather is only one factor, but it can really affect your travel plans, especially if you're planning an extended stay in Winchester. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall. ### What are the must-see places to visit in Winchester? > Winchester is known for its lakeside. Rhododendron State Park and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. 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