Title: Top Winchester Cabin Rentals | 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 # Find Cabins in Winchester for Rent from CA $295 ![](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 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=CABIN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=CABIN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=CABIN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=CABIN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Cabin Rentals ![Exterior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/6cd80eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/fc0d0a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/57ed5fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/w956h736x34y34-3e10a6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wellness Getaway with a Personal Sauna, and Private River Beach! Newfane 10/10 Exceptional (1) "The folks are SUPER and made me feel very welome" CA $189 CA $358 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Newfane-Hotels-Your-Comprehensive-Wellness-Escape-Sauna-And-Private-Beach.h106418444.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74980000/74973500/74973482/e470a325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74980000/74973500/74973482/ed434051.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/75000000/74980000/74973500/74973482/5c20f721.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74980000/74973500/74973482/w3964h3024x0y0-3525ed3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna Fitzwilliam 10/10 Exceptional (13) "Loved the area" CA $178 CA $295 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Fitzwilliam-Hotels-Romantic.h74973482.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=2025-10-26&endDate=2025-10-27®ionId=3000447144&adults=2&lodging=CABIN&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-Cabins.d3000447144-aaCabins.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cabins.d3000447144-aaCabins.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 "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) ![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 "Excellent staff at front desk and Lori who serves breakfast is wonderful " [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.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 Cabin Rentals information | Number of reviews | 13 | | --- | --- | | Accommodation | 23 Cabin Rentals | | Lowest Price | CA $295 | | Highest Price | CA $358 | ## Frequently asked questions ### What are the best cabins near Winchester? > Vacation in one of our 276 cabins in Winchester and be rewarded with striking scenery, outdoor adventure and long-lasting memories. [Private And Artistic Cabin, Pet Friendly](https://www.expedia.ca/West-Pawlet-Hotels-Private-And-Artistic-Cabin.h33668606.Hotel-Information) is the place to go for an unplugged getaway. [Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East](https://www.expedia.ca/Charlemont-Hotels-Sfa-Lodge-Log-Cabin-4-Bd-2-Ba-Nestled-In-The-Woods-5-Mins-From-Berkshire-East.h33693860.Hotel-Information) is another good choice if you'd love to spend time in Mother Nature. ### Are there cheap cabins in Winchester? > Whether you'd prefer to stay a hop and a skip from the water or on the top of a mountain, we have a fantastic variety of cheap cabins in Winchester to look into. Priced from CA $295 to CA $358 a night, your ideal cabin rental is waiting right here.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### What are the best mountain cabins near Winchester? > If you're craving crisp air and stunning views, escape the city and stay in a Winchester mountain cabin. Get your head in the clouds at [Cabin - Little House On The Lake In The Forest](https://www.expedia.ca/Andover-Hotels-Little-House-On-The-Lake-In-The-Forest.h58316771.Hotel-Information). This lofty rental has all the ingredients for a fantastic escape, including a wood stove and a microwave oven. Alternatively, experience a taste of the mountain lifestyle at [This Is It Fabulous Vermont Cabin W](https://www.expedia.ca/West-Halifax-Hotels-This-Is-It-Stunning-Vermont-Views-W-25-Acres-To-Explore-Its-Almost-Heaven.h18993521.Hotel-Information). It offers a wood stove, winery tours and more. ### What are the best river cabins near Winchester? > If you're looking for a comfy escape by the water, a Winchester river cabin will be just the thing. Put your feet up at [Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet](https://www.expedia.ca/West-Dover-Hotels-Secluded-Log-Home-13-Mi-From-Liftslodge-Waterfalls.h32545319.Hotel-Information) and let any worries drift downstream. Handy amenities here include a wood stove and snowsport activities. Another superb riverside retreat is [Warm And Inviting Jamaica Cabin W](https://www.expedia.ca/Jamaica-Hotels-NEW-Warm-Inviting-Jamaica-Cabin-Ski-Hike.h57568037.Hotel-Information). It offers a wood stove, a firepit and more. ### What are the best cabins with pools near Winchester? > If you love the thought of every day being a pool day, make a break for [Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna](https://www.expedia.ca/Wardsboro-Hotels-Charming-Traditional-Log-Cabin-In-Between-Mt-Snow-And-Stratton-With-Saunawifi.h33563397.Hotel-Information). It's one of our top cabin rentals with a pool near Winchester and offers amenities like a swimming pool and a porch. [Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet](https://www.expedia.ca/West-Dover-Hotels-Secluded-Log-Home-13-Mi-From-Liftslodge-Waterfalls.h32545319.Hotel-Information) is another superb place to spend lazy days poolside. A porch, a patio and fun times are up for grabs here. ### Can I find beach cabins near Winchester? > Wake up and be moments from a beautiful shoreline when you lock in a stay at a Winchester beach cabin rental. Sun, fun and family time should be your main priorities at [Cabin - Relax, Reconnect And Enjoy](https://www.expedia.ca/Sand-Lake-Hotels-Lakeside-Cabin-Pumpkin-Carving.h57343854.Hotel-Information). It offers on-site watersports and children's activities. Or, throw your bag down and spend a few nights at [Cabin - Lakefront - King - Petsok - W And D](https://www.expedia.ca/Ashford-Hotels-Lakefront-Cabin-W-KING-Bed-Amazing-Lake-Views.h89789856.Hotel-Information). Handy amenities here include on-site watersports and clothes washing facilities. ### What are the best weekend cabin rentals in Winchester? > Whether you're planning a mini break with your beau or the entire family, we'll help you find your dream weekend cabin getaway. One superb example? [Cabin - Little House On The Lake In The Forest](https://www.expedia.ca/Andover-Hotels-Little-House-On-The-Lake-In-The-Forest.h58316771.Hotel-Information). Featuring on-site watersports and a patio, you'll adore the natural surroundings here. [This Is It Fabulous Vermont Cabin W](https://www.expedia.ca/West-Halifax-Hotels-This-Is-It-Stunning-Vermont-Views-W-25-Acres-To-Explore-Its-Almost-Heaven.h18993521.Hotel-Information) is another good place where you can hit pause. Book a couple of nights at this retreat which offers a patio and a firepit. ### What are the best cabin prices in Winchester? > Whether you're on a budget or want to splurge on your next trip, you'll find what you're after on Expedia. At the moment, you can get a Winchester cabin from only CA $295 per night. ### Can I find log cabins in Winchester? > If you're longing for a quieter pace of life, you'll discover it at one of our log cabins in Winchester. For example, [Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna](https://www.expedia.ca/Wardsboro-Hotels-Charming-Traditional-Log-Cabin-In-Between-Mt-Snow-And-Stratton-With-Saunawifi.h33563397.Hotel-Information). Spend your days here snow shoeing and tubing and then return home to its many comforts. Time also seems to go slower at [Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet](https://www.expedia.ca/West-Dover-Hotels-Secluded-Log-Home-13-Mi-From-Liftslodge-Waterfalls.h32545319.Hotel-Information). When you're in the mood to explore beyond your cozy digs, snow shoeing and canoeing opportunities are close by. ### What are the highest-rated cabins in Winchester? > There are some properties that are hard to fault. [Cabin: Private Hot Tub, Walk To Pats Peak Ski Area](https://www.expedia.ca/Manchester-Hotels-New-Cabin-W-Private-Hot-Tub-Walk-To-Pats-Peak.h46550649.Hotel-Information) is a great example. With such an impressive rating, it comes with handy amenities like a patio and a fireplace. Another excellent option is [Brook Road Cabin](https://www.expedia.ca/Goshen-Hotels-Brook-Road-Cabin.h46558945.Hotel-Information). A barbecue grill and a kitchen are a couple of the conveniences you'll appreciate here. ### Why should I book a cabin in Winchester? > Affordability, rustic charm, nature-filled surroundings — there are loads of reasons for you to choose a Winchester cabin. Leave behind the noise of the concrete jungle and rise with the sound of songbirds and wildlife. There's ample adventure just around the corner too. Whether you're on vacation with family members, friends or your partner, you'll locate the ideal cabin on Expedia. ### What are the top nature cabins in Winchester? > Our nature cabins in Winchester come in plenty of styles, shapes and budgets, but there's one thing they have in common — excellent access to the great outdoors. [Warm And Inviting Jamaica Cabin W](https://www.expedia.ca/Jamaica-Hotels-NEW-Warm-Inviting-Jamaica-Cabin-Ski-Hike.h57568037.Hotel-Information) is a magnet for nature buffs. Amenities such as a fireplace and a firepit only make it better. Whether you want to slip your feet into hiking boots or just put them up, you can do it at [Cabin - Beautiful Mt Area With Beautiful Scenic Views](https://www.expedia.ca/West-Dover-Hotels-Beautiful-Mt-Area-With-Beautiful-Scenic-Views-Close-To-Mount-Snow-Ski-Resort.h70405007.Hotel-Information). Another top pick, it offers a patio and a barbecue grill. ### What are some of the best cabins near Vermont Country Store in Winchester? > [](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information)[Cabin - Charming Fully Renovated One - Room Schoolhouse On 22+ Acres](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information) is one of the most popular cabins in Vermont Country Store. Thoughtful amenities, a beautiful backdrop and activities such as ice skating nearby and hiking make it the perfect escape. [Log Cabin - Cozy, Quaint And Scenic And Ready For Your Enjoyment](https://www.expedia.ca/Chester-Hotels-Log-Cabin-Cozy.h30594857.Hotel-Information) is another place where nature and adventure combine. 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