Title: Winchester Station Cottages | Expedia.ca [Boston Travel Guide](https://expedia.ca/Boston.dx178239)[Winchester Station Hotels](https://expedia.ca/Winchester-Station-Hotels.d6209683.Travel-Guide-Hotels)[Flights to Boston](https://expedia.ca/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights)[Things to do in Boston](https://expedia.ca/Things-To-Do-In-Boston.d178239.Travel-Guide-Activities)[Boston Car Rentals](https://expedia.ca/Car-Rentals-In-Boston.d178239.Car-Rental-Guide)[Boston Vacation Packages](https://expedia.ca/Boston.d178239.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) # Search Winchester Station Cottage 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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6209683&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6209683&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6209683&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6209683&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Station%2C+Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=6209683&latLong=42.452592%2C-71.137235&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Station%2C+Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=6209683&latLong=42.452592%2C-71.137235&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Station%2C+Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=6209683&latLong=42.452592%2C-71.137235&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Station%2C+Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=6209683&latLong=42.452592%2C-71.137235&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Station%2C+Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=6209683&latLong=42.452592%2C-71.137235&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Station%2C+Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=6209683&latLong=42.452592%2C-71.137235&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=VACATION_HOME) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Station%2C+Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=6209683&latLong=42.452592%2C-71.137235&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Station-Cottages.d6209683-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Station-Cottages.d6209683-aaCottages.Travel-Guide-Accommodation) ## Top Winchester Station Hotel Reviews ![Hampton Inn Boston Woburn](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979980/895877cc_y.jpg) ### Hampton Inn Boston Woburn 10/10 Excellent "Very good" [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Woburn-Boston.h38979980.Hotel-Information) ![Sonesta Simply Suites Boston Burlington](https://images.trvl-media.com/lodging/1000000/550000/544800/544728/a4844b99_y.jpg) ### Sonesta Simply Suites Boston Burlington 10/10 Excellent "Stay was great. Neal at the front desk was very accommodating and friendly. Had an issue, quickly resolved. Well priced for the area. Private. Great location." [](https://expedia.ca/Boston-Hotels-Sonesta-Simply-Suites-Boston-Burlington.h544728.Hotel-Information) ![Studio Allston Hotel](https://images.trvl-media.com/lodging/23000000/22760000/22757100/22757092/a522d616_y.jpg) ### Studio Allston Hotel 10/10 Excellent "Great stay as usual! They had my room preferences on file and filled to perfection when I got there! Love this hotel." [](https://expedia.ca/Boston-Hotels-Studio-Allston-Hotel.h22757092.Hotel-Information) ![The Row Hotel at Assembly Row, Autograph Collection](https://images.trvl-media.com/lodging/23000000/22940000/22935400/22935326/fbdd2ef8_y.jpg) ### The Row Hotel at Assembly Row, Autograph Collection 10/10 Excellent "Great place to stay" [](https://expedia.ca/Boston-Hotels-The-Row-Hotel-At-Assembly-Row.h22935326.Hotel-Information) ![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/66098bc6_y.jpg) ### The Charles Hotel 10/10 Excellent "Everything was great" [](https://expedia.ca/Boston-Hotels-The-Charles-Hotel.h15861.Hotel-Information) ![Hilton Boston/Woburn](https://images.trvl-media.com/lodging/1000000/20000/10600/10575/645b1b52_y.jpg) ### Hilton Boston/Woburn 10/10 Excellent "Just overall best stay." [](https://expedia.ca/Boston-Hotels-Hilton-BostonWoburn.h10575.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Absolutely. Yes to all. Above and beyond " [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![AC Hotel by Marriott Boston Cambridge](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191005/3f29eb44_y.jpg) ### AC Hotel by Marriott Boston Cambridge 10/10 Excellent "Very clean and new space, and friendly, helpful staff. The room was very comfortable, and the cleaning staff were very thorough. Thank you!" [](https://expedia.ca/Boston-Hotels-AC-Hotel-By-Marriott-Boston-Cambridge.h15191005.Hotel-Information) ![Cambria Hotel Boston Somerville](https://images.trvl-media.com/lodging/76000000/75900000/75893900/75893900/50a5a2bc_y.jpg) ### Cambria Hotel Boston Somerville 10/10 Excellent "Room was spacious and had a lounge area which " [](https://expedia.ca/Boston-Hotels-Cambria-Hotel-Boston-Somerville.h75893900.Hotel-Information) ## Find out more about Winchester Station #### What types of Cottages can I find in Winchester Station? When you’re looking for Winchester Station Cottages in 2026, you can use Expedia’s filters to find accommodation that’s family-friendly or business-friendly, and narrow down your search results by amenities, price per night, and much more. For example, you can search for Cottages that welcome pets, or one with accessibility features. You’ll find a range of places to stay to suit every budget, so if you're looking for cheap Cottages in Winchester Station, use our simple search function to help you secure a good deal. If the exact location of Cottages is important to you, try our map facility to view available places in relation to each other and to Winchester Station. #### How much do Cottages cost in Winchester Station? Prices for Winchester Station Cottages can start from as little as \* in 2026\. The cost per night varies depending on several factors, including the amenities on offer at Cottages, the exact location of Cottages and how far they are from Winchester Station, as well as how high the demand for accommodation is near Winchester Station on the dates of your booking. At Expedia, we cater for every budget, so if you’re looking for cheap Cottages in Winchester Station, you can sleep easy knowing that we’ll help you to secure some of the very best deals on offer. #### How to find the best deals on Winchester Station Cottages? Expedia’s search function can help you find a great deal on Winchester Station Cottages. Changing the sort order of your search results can help you to find cheap Cottages in Winchester Station at a glance. If you have a specific price range in mind, try selecting minimum and maximum prices per night to narrow your results. You can also filter by guest ratings and star ratings to find some of the best offers for Cottages within your budget. Don’t forget, if you’re an Expedia Rewards member, you can use the ‘Member Prices’ filter to make instant savings on your booking. #### Why should I choose Expedia to book Winchester Station Cottages? One of the many benefits of booking Winchester Station Cottages with Expedia is the clear and simple search function. When you use the many filters on offer, you can easily compile a shortlist of fantastic places to stay, and make comparisons between the different Cottages so that you can choose exactly what you need. At Expedia, it’s possible to create your own customized package and make great savings by booking flights, car hire, and more at the same time as Winchester Station Cottages. And don’t forget that with free membership to Expedia Rewards, you can earn points on all eligible purchases, and build your points total to use towards future travel. #### What is the cancellation policy on booking Winchester Station Cottages? It’s often possible to change or cancel bookings at Winchester Station Cottages without a fee, but it depends on the rules and restrictions of the various Cottages. Many booking options offer a window of flexibility, for example a full refund if you cancel more than 24 or 48 hours before Winchester Station arrival dates. It’s best to check the policies of the individual Cottages before making a booking, if flexibility is important to you. You can filter for the ‘Fully refundable’ payment type when you search for Cottages. You can also view the terms of the different Cottages at any time by checking the details of your booking at Expedia. \*Prices and availability are subject to change. 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