Title: Top Winchester Cabin Rentals | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975869849.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975869849.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975869849.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248635975869849.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Cabins in Winchester for Rent from CA $961 ![](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=553248635975869849&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=CABIN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=CABIN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=CABIN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=CABIN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Cabin Rentals ![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/edf60411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/565807cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guesthouse Cabin vacation rentals in Berkshire County Sheffield 10/10 Exceptional (9) "Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom S. CA $544 CA $961 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.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=2025-11-12&endDate=2025-11-13®ionId=553248635975869849&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.d553248635975869849-aaCabins.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cabins.d553248635975869849-aaCabins.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Delamar West Hartford](//images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg) ### Delamar West Hartford 10/10 Excellent "Valet+Welcome Proseccos & Bottled Water=👍" [](https://expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information) ![Avon Old Farms Hotel](//images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg) ### Avon Old Farms Hotel 10/10 Excellent "We did not have breakfast. The staff was friendly. However, they should stock more complimentary items such as hot tea and not just say "oh, we are out". " [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Days Inn by Wyndham Torrington](//images.trvl-media.com/lodging/1000000/50000/50000/49932/dd052437_y.jpg) ### Days Inn by Wyndham Torrington 10/10 Excellent "Very simple, clean comfortable room" [](https://expedia.ca/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.Hotel-Information) ![Home2 Suites by Hilton Bristol](//images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/74bd7e00_y.jpg) ### Home2 Suites by Hilton Bristol 10/10 Excellent "Room was immaculate. Nice spacious lobby with plenty of areas to sit. Nice outdoor enclosed patio in the back to hang out. Breakfast was very good, egg bites, turkey bacon, waffle machine, yogurt and many more options. " [](https://expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Blackberry River Inn](//images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd_y.jpg) ### Blackberry River Inn 10/10 Excellent "Charming place. No tv. Small room. Good breakfast. " [](https://expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information) ![Extended Stay America Suites Hartford Farmington](//images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg) ### Extended Stay America Suites Hartford Farmington 10/10 Excellent "Thank Staff was Great! Very very nice and attentive. Room very clean, Quiet we rested well! The Great was awesome and exit was wonderful. Parking was smoothe. We’ll return to enjoy another quiet night get away. " [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![The Farmington Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 10/10 Excellent "Good location. Staff was very friendly and helpful. " [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![Sheraton Hartford Hotel at Bradley Airport](//images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg) ### Sheraton Hartford Hotel at Bradley Airport 10/10 Excellent "Airport. " [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ![Americas Best Value Inn Torrington CT](//images.trvl-media.com/lodging/1000000/10000/5800/5738/a9b48332_y.jpg) ### Americas Best Value Inn Torrington CT 10/10 Excellent "Excellent parking." [](https://expedia.ca/Torrington-Hotels-Americas-Best-Value-Inn-Torrington-CT.h5738.Hotel-Information) ## Find out more about Winchester ## Winchester Cabin Rentals information | Number of reviews | 9 | | --- | --- | | Accommodation | 13 Cabin Rentals | | Lowest Price | CA $961 | | Highest Price | CA $961 | ## Frequently asked questions ### What are the best cabins near Winchester? > From cute and cozy to big and luxurious, there are 247 cabins on offer in and around Winchester. Some popular options include [Log Cabin On A Lake With Private Dock And Beach One Hour From Nyc](https://www.expedia.ca/Holmes-Hotels-Log-Cabin-On-A-Lake-With-Private-Dock-Beach-One-Hour-From-NYC.h34011469.Hotel-Information) and [Log Cabin Living On The Esopus Creek](https://www.expedia.ca/Saugerties-Hotels-Log-Cabin-Living-On-The-Esopus-Creek.h33507304.Hotel-Information). ### Are there cheap cabins near Winchester? > Priced from CA $961 to CA $961 per night, getting away with loved ones has never been easier or cheaper. Book one of our cheap cabins near Winchester and enjoy plenty of outdoor fun without emptying your bank account.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? > Choose a mountain cabin near Winchester and be rewarded with dramatic views, outdoor adventure and an experience that's hard to forget. [1890's Log Cabin ~ 230 Acre Private Reserve](https://www.expedia.ca/Wallkill-Hotels-1890s-Mountain-Lodge-In-The-Gunks-W-AMAZING-150-Waterfall-On-Private-Reserve.h55511765.Hotel-Information) is a tough act to beat. Located high in the hills, you'll find useful amenities like winery tours and a microwave oven here. [The Luxury Lodge - Ski, Ride, Golf](https://www.expedia.ca/Hunter-Hotels-THE-LUXURY-LODGE-SKI.h57226527.Hotel-Information) is another ideal property. It comes with nearby hunting activities, a microwave oven and natural surroundings that'll make you swoon. ### What are the best river cabins near Winchester? > If you're searching for a homely hideout by the water, a Winchester river cabin is an excellent choice. Stay at [Cabin - Charming, Quiet, River Front](https://www.expedia.ca/Hillsdale-Hotels-Charming.h22161514.Hotel-Information) and let all your troubles drift downstream. Handy amenities here include snowsport activities and skiing facilities. Another leading riverside retreat is [Cabin - Romantic Retreat](https://www.expedia.ca/Kingston-Hotels-Romantic-Lakefront-Retreat.h27263490.Hotel-Information). Guests have use of on-site watersports, snowsport activities and more. ### What are the best cabins with pools near Winchester? > If you like the idea of every day being a pool day, make your way to [Cabin - Romantic Retreat](https://www.expedia.ca/Kingston-Hotels-Romantic-Lakefront-Retreat.h27263490.Hotel-Information). It's one of our most popular cabin rentals with a pool near Winchester and comes with useful amenities like on-site watersports and a swimming pool. [Country Cabin In Woodstock, Ny](https://www.expedia.ca/Woodstock-Hotels-Country-Cabin-In-Woodstock.h38372371.Hotel-Information) is another place to spend your days splashing around. A swimming pool, a fireplace and good times are what you can expect here. ### Can I find beach cabins near Winchester? > Wake up and be steps from shimmering blue waters when you escape to a Winchester beach cabin rental. Sunshine and fun should be your top priorities at [Cabin - Relax, Reconnect And Enjoy](https://www.expedia.ca/Sand-Lake-Hotels-Lakeside-Cabin-Pumpkin-Carving.h57343854.Hotel-Information). This popular pick comes with on-site watersports and children's activities. Or, toss your bag down and make yourself comfy at [Rustic Lakeside Cabin At White Gate Farm](https://www.expedia.ca/Mystic-New-London-Hotels-Rustic-Lakeside-Cabin-At-White-Gate-Farm.h54202033.Hotel-Information). Handy amenities here include on-site watersports and beach sun loungers. ### What are the best weekend cabin rentals in Winchester? > Nothing compares to a weekend cabin getaway after a busy week at work. Ditch the office cubicle for a few days in nature at [1890's Log Cabin ~ 230 Acre Private Reserve](https://www.expedia.ca/Wallkill-Hotels-1890s-Mountain-Lodge-In-The-Gunks-W-AMAZING-150-Waterfall-On-Private-Reserve.h55511765.Hotel-Information). A tennis court and a patio are a few of the amenities it offers. You can also forget all about work at [The Luxury Lodge - Ski, Ride, Golf](https://www.expedia.ca/Hunter-Hotels-THE-LUXURY-LODGE-SKI.h57226527.Hotel-Information). Put your bags down here and take advantage of on-site watersports and a patio. ### What are the best cabin prices near Winchester? > Whether you're traveling on a budget or want to indulge on your next trip, you'll find what you're looking for with Expedia. At the moment, you can pick up a Winchester cabin from as little as CA $961 per night. ### Can I find log cabins in Winchester? > If you find yourself pining for a slower pace, you'll discover it at one of our log cabins in Winchester. For instance, [1890's Log Cabin ~ 230 Acre Private Reserve](https://www.expedia.ca/Wallkill-Hotels-1890s-Mountain-Lodge-In-The-Gunks-W-AMAZING-150-Waterfall-On-Private-Reserve.h55511765.Hotel-Information). Spend your days here shore fishing and hiking and then return home to kick back among its comforts. Time also appears to go slow at [Log Cabin On A Lake With Private Dock And Beach One Hour From Nyc](https://www.expedia.ca/Holmes-Hotels-Log-Cabin-On-A-Lake-With-Private-Dock-Beach-One-Hour-From-NYC.h34011469.Hotel-Information). When you're ready to wander beyond your cozy digs, horse riding and canoeing opportunities are nearby. ### What are the highest-rated cabins in Winchester? > With an impressive rating, it's not hard to understand why [Rustic Lakeside Cabin At White Gate Farm](https://www.expedia.ca/Mystic-New-London-Hotels-Rustic-Lakeside-Cabin-At-White-Gate-Farm.h54202033.Hotel-Information) is such a favourite with travellers. Some amenities here include on-site watersports and a private beach. [Ultimate Cabin Getaway With Hot](https://www.expedia.ca/Kingston-Hotels-Ultimate-Cabin-Getaway-With-Hot-Tub-And-Fire-Pit.h68288985.Hotel-Information) is another excellent choice. Quality conveniences including a patio and a firepit will help make your stay a comfortable one. ### Why should I book a cabin in Winchester? > For a nature-filled escape at a great price, there's nothing better than a cabin. Imagine rising to the sounds of the countryside and having breakfast on your deck surrounded by stunning vistas. Rent a cabin in Winchester and leave behind the hustle and bustle of modern life. Whether they're beachside, lakeside or up a mountain, cabins offer a unique, rustic experience you'll never forget. ### What are the top nature cabins in Winchester? > With lots of charm and creature comforts, [Cabin - Charming, Quiet, River Front](https://www.expedia.ca/Hillsdale-Hotels-Charming.h22161514.Hotel-Information) is one of our top nature cabins in Winchester. But with countless things to see and do close by, don't spend all your time chilling indoors. Activities such as nearby sailing and nearby motor boating are waiting for you. [Cabin - Romantic Retreat](https://www.expedia.ca/Kingston-Hotels-Romantic-Lakefront-Retreat.h27263490.Hotel-Information) is another getaway where you can hang out in nature. 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