Title: Winchester, MA Cottage Rentals from $249 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx175481)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d175481.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d175481.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d175481.Destination-Travel-Guides) ![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester cottages ![Exterior](https://images.trvl-media.com/lodging/120000000/119450000/119449800/119449739/cb444172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119450000/119449800/119449739/e6c1304a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119450000/119449800/119449739/146c15df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119450000/119449800/119449739/457d1e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Witchy Hideaway Cottage; Close to Beaches, Salem & Train to Boston [](https://www.expedia.com/Boston-Hotels-Witchy-Hideaway-Cottage-With-AC.h119449739.Hotel-Information) Beverly 10/10 Exceptional (5 reviews) "Great little spot if you need to stay close to downtown Salem. Would recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Corey W. $223 nightly $249 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Witchy-Hideaway-Cottage-With-AC.h119449739.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.com/Hotel-Search?startDate=2026-03-29&endDate=2026-03-30®ionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_175481) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=APART_HOTEL) Apartments [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=APARTMENT) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=CONDO) Villas [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=VILLA) Cottages [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=COTTAGE) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=HOUSE_BOAT) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cottages.d175481-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cottages.d175481-aaCottages.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 8/10 Good "Rooms are a bit small, and the sheets we're a little dirty, there were some missed spots, the hotel was gorgeous tho. " [](https://expedia.com/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "Great location, we took the blue line subway from the airport and hotel was across the street when we arrived. We didn't need a car. We walked everywhere, even in the cold weather. Rooms could use an upgrade but other then that they are fine. Staff was helpful and friendly. " [](https://expedia.com/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Club Quarters Hotel Faneuil Hall, Boston](https://images.trvl-media.com/lodging/1000000/70000/67000/66938/0c21f6a5_y.jpg) ### Club Quarters Hotel Faneuil Hall, Boston 8/10 Good "Everything was great" [](https://expedia.com/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Loved our stay. Staff was the best. " [](https://expedia.com/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/f2f31351_y.jpg) ### citizenM Boston North Station 10/10 Excellent "My husband and I had the best stay with CitizenM North Station. The location was amazing and close to a bunch of great things. The room was great and the staff were phenomenal. We enjoyed our time around Andrew and Maddy who made our experience 10 times better with excellent service and great conversations. They were both very attentive and overall a great time. " [](https://expedia.com/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![The Midtown Hotel MOD Collection by Sonesta](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/e1e25d35_y.jpg) ### The Midtown Hotel MOD Collection by Sonesta 6/10 Okay "The shower in our room had no curtain. it was so messy to shower. When I told the front desk, the staff asked what could they do to compensate and she will talk to the supervise but nothing ever happened. " [](https://expedia.com/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/d1e2c1a3_y.jpg) ### Omni Boston Hotel at the Seaport 2/10 Terrible "Employees wrre so very rude" [](https://expedia.com/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/c254df3c_y.jpg) ### The Godfrey Hotel Boston 10/10 Excellent "Everything was great " [](https://expedia.com/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/de788f3d_y.jpg) ### Omni Parker House 10/10 Excellent "Very comfortable bed, and pillows! Short walk to TD Center and restaurents and bars." [](https://expedia.com/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ## Find out more about Winchester ## Winchester Cottages information | Number of reviews | 5 | | ----------------- | ----------- | | Accommodation | 34 Cottages | | Lowest Price | $249 | | Highest Price | $249 | ## Frequently asked questions ### Why book your cottage in Winchester with Expedia? ### How can I find cheap cottages in Winchester? ### What is there to do in Winchester near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Boston Hotels ](https://www.expedia.com/Boston-Hotels.d178239.Travel-Guide-Hotels) - [B&B in Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Bed-And-Breakfast.d6209680-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Condos.d6209680-aaCondos.Travel-Guide-Accommodation) - 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