Title: Winchester Apartment Rentals from CA $215 | 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 Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Apartments ![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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/5cd29bde.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 (27) "My stay was what I wanted – quiet and time to study and pray. The town has many beautiful brick buildings and quaint shops for shopping. I thoroughly enjoyed my stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Betty D. CA $101 CA $215 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Peterborough-Hotels-Studio-Apt-With-Full-Kitchen-1-Minute-Stroll-Over-Picturesque-Bridge-Into-Town.h102238328.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/c9f7c522.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) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/b0dd8181.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) ### 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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy C. CA $119 CA $288 total includes taxes & fees Nov 30 - Dec 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) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/5e42b791.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) ### 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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anicia K. CA $196 CA $426 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Jacksonville-Hotels-Lake-Whitingham-Mount-Snow-Area-Village-Garden-Apartment-2-BR.h108320042.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) ![Living area](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/6d6cf781.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 $91 CA $291 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Greenfield-Hotels-Charming-Country-Chic-1BR-In-Greenfield-King-Bed.h120530639.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/475f2a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/9832d1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/76bef906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/6d3522c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Twin beds on 1st floor with En-suite bathroom. Shelburne Falls CA $123 CA $245 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Shelburne-Falls-Hotels-2-Twin-Beds-On-1st-Floor-With-En-Suite-Bathroom.h120039334.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) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/4f40d5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/724bdf50.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 $617 total includes taxes & fees Nov 4 - Nov 5 [](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/121000000/120040000/120039400/120039328/b2692a7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039328/0077e74f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039328/c36ab3a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039328/f24c9d86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rose room Victorian home queen bed private bath Shelburne Falls CA $159 CA $289 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Shelburne-Falls-Hotels-Rose-Room-Victorian-Home-Queen-Bed-Private-Bath.h120039328.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/06c02e86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/5bbd846e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/d791261d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/4aa8f6ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rose wisteria 4 guests 2 bedrooms-full+queen beds Shelburne Falls CA $192 CA $369 total includes taxes & fees Nov 3 - Nov 4 [](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=2025-11-15&endDate=2025-11-16®ionId=3000447144&adults=2&lodging=APARTMENT&sort=RECOMMENDED&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 ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "YES, the room was SPOTLESS!!! An indoor Pool, Sauna & Continental Breakfast made this stay a PLUS!!! (Waffles, Toast, Coffee, Bagels, Cereal & Fresh Fruit). A definite choice for another visit!!!" [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![The Inn At Crumpin Fox](//images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/b4ead30a_y.jpg) ### The Inn At Crumpin Fox 10/10 Excellent "Great place along our travels! Friendly customer service at check in and a clean and comfortable room. " [](https://expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.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 "Best value in New England! Staff is supportive and site is super clean. Decor is nice. Comfy beds. Subpar breakfast but who cares?! Free coffee, and the food is a bonus... and again, you can't beat the value!" [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![The Colonial Hotel](//images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "N/A" [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Great hotel with comfortable and clean rooms and a great bar and cinema downstairs. The historical fixtures and fittings make it a special and interesting place. Staff are very helpful and fixed a problem with a TV within an hour." [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.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 "This was one of my better hotel stays in the area - bed was very comfortable, nice bathroom, quiet space at a reasonable price." [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![The Putney Inn](//images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "The Putney Inn is a great place to stay!! The people who work there are very nice and the location is great!" [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Riverside Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg) ### Riverside Hotel, an Ascend Collection Hotel 10/10 Excellent "Perfect and peaceful! It surpassed my expectations. Would love to come back and stay again." [](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![Courtyard by Marriott Keene Downtown](//images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/7bc7321f_y.jpg) ### Courtyard by Marriott Keene Downtown 10/10 Excellent "Appreciated the location convenient" [](https://expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) ## Find out more about Winchester ## Winchester Apartments information | Number of reviews | 30 | | --- | --- | | Accommodation | 35 Apartments | | Lowest Price | CA $215 | | Highest Price | CA $617 | ## 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: [Riverside Retreat – Cozy 2-Story Getaway!](https://www.expedia.ca/Montague-Hotels-Cozy-2-Bedroom-Unit-With-Private-Backyard.h90172818.Hotel-Information): Located 14.5 mi/23.3 km away in Montague. Free WiFi, private patios, and Smart TVs are included. [Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires](https://www.expedia.ca/Greenfield-Hotels-Charming-Country-Chic-1BR-In-Greenfield-King-Bed.h120530639.Hotel-Information): 16.6 mi/26.7 km away in Greenfield. ### 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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