Title: Winchester Vacation Home Rentals from CA $285: Search Top Private Vacation Homes for Rent | 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 # Winchester Vacation Rentals ![](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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Vacation Homes ![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/79a253e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/d695e72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, offices](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/512b2604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/01ff54d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely 2nd Floor Apartment Greenfield 10/10 Exceptional (41) "Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shanyn CA $162 CA $285 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/a4ec6964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/48ea3a3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w2207h1242x0y0-824667c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/3315ad26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly Hilltop House In Putney Vermont Putney 9.4/10 Exceptional (56) "The property was beautiful--great views, super peaceful, and fabulous hosts. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Louis T. CA $175 CA $356 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/d9a32dde.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/112000000/111140000/111133500/111133438/16a722ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/17e097bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/ab251044.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Glass House nestled in the Vermont wilderness! Guilford 10/10 Exceptional (1) "The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Grant D. CA $309 CA $727 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Brattleboro-Hotels-Stunning-Glass-House-Nestled-In-The-Vermont-Wilderness.h111133438.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/78692cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/4702110d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/fd35a312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/f112c530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Couples 2 Bedroom Retreat-Close to Shelburne Falls Colrain 10/10 Exceptional (4) "This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KayKay S. CA $238 CA $520 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Colrain-Hotels-Couples-2-Bedroom-Retreat-Hot-Tub-Air-Hockey-Close-To-ShelburneFalls.h113519074.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/ae0971bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/4e846ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/f38617c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/bf6afd61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Home Walk to Downtown! Keene 10/10 Exceptional (1) "Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Xilin J. CA $400 CA $974 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/a9ea01f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/fc7ddd03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/8ebf8854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/b4c71f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Hot Tub Escape Keene 9.6/10 Exceptional (21) "Nice house in a nice location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rob B. CA $280 CA $511 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/7d6a1254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/bf925c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/314d0c95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/0226cb00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MtSnow\* HotTub\* Pool \* AirHockey\*PingPong \* Darts Wilmington CA $302 CA $906 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Wilmington-Hotels-MtSnow-HotTub-Pool-AirHockeyPingPong-Darts.h119097866.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/458d1d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/eb8c4f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/aef5544c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/8fcd0ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FaLL Western Mass Getaway-Airhockey-Firepit Colrain 9.8/10 Exceptional (37) "Great place and convenient to get to and from Berkshire East." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey B. CA $409 CA $911 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/4f8e6e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/482b0eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/fa175e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/1343f198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region Dublin 10/10 Exceptional (25) "Good place to stay during a wedding week" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronique S. CA $588 CA $1,007 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Dublin-Hotels-5-Bedroom-Cozy-New-England-Home-Cobb-Meadow-House.h74153605.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/25afdf4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/7d3e26e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/a5533dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109200000/109193700/109193661/b09ae2c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Beautiful Finnish Cabins with Sauna on Lake Monomonac Rindge CA $1,006 CA $1,660 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Rindge-Hotels-3-Beautiful-Finnish-Cabins-With-Sauna-On-Lake-Monomonac.h109193661.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=2025-11-08&endDate=2025-11-09®ionId=3000447144&adults=2&lodging=VACATION_HOME&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-Private-Vacation-Homes.d3000447144-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Private-Vacation-Homes.d3000447144-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Hampton Inn & Suites Greenfield](//images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg) ### Hampton Inn & Suites Greenfield 10/10 Excellent "Clean, well appointed, very nice staff." [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![The Colonial Hotel](//images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "The property is beautiful!" [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.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 friendly and the hotel was clean" [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![The Putney Inn](//images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Parking lot was being sealed but smoke area to park close by. Bed was very comfortable and area was quiet even though close to freeway. " [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Vikings Villages Resort](//images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 10/10 Excellent "Unique, well executed hotel concept in an unbelievably beautiful area. Easy drive to restaurants. Clean room, friendly staff, easy access. We loved it!" [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.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 "Convenient, great location. We will be back again. Thank you Crumpin Fox." [](https://expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Very nice " [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.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 "Super cute place! Would stay here again" [](https://expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.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 "Was a great place my mom and I stayed. Very clean and the staff were great!! " [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ## Find out more about Winchester ## Winchester Vacation Homes information | Number of reviews | 177 | | --- | --- | | Accommodation | 110 Vacation Homes | | Lowest Price | CA $285 | | Highest Price | CA $1,660 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Monadnock Region](https://www.expedia.ca/3Star-Monadnock-Region-Hotels.s30-0-d553248635975749761.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Keene](https://www.expedia.ca/4Star-Keene-Hotels.s40-0-d6057413.Travel-Guide-Filter-Hotels) - [Hotels near Asbury United Methodist Church](https://www.expedia.ca/Asbury-United-Methodist-Church-Hotels.0-l6265749-0.Travel-Guide-Filter-Hotels) - [Castles in Cheshire County](https://www.expedia.ca/Cheshire-County-Castles.d553248635976430851-aaCastles.Travel-Guide-Accommodation) - [B&B in Chesterfield](https://www.expedia.ca/Chesterfield-Bed-And-Breakfast.d6052872-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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