Title: 20 Best B&B in Winchester, MA - Bed and Breakfast from $166 | 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 Next weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester bed & breakfast ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111430000/111428500/111428434/14f525ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111430000/111428500/111428434/4c5471b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/112000000/111430000/111428500/111428434/a17581c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/112000000/111430000/111428500/111428434/9c240fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homestay In Fields Corner Area Boston [](https://www.expedia.com/Boston-Hotels-Homestay-In-Fields-Corner-Area-Boston.h111428434.Hotel-Information) Dorchester 8.6/10 Excellent (21 reviews) "The entire place looks really amazing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeremiah $75 nightly $86 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Homestay-In-Fields-Corner-Area-Boston.h111428434.Hotel-Information) ![Classic Triple Room | Interior](https://images.trvl-media.com/lodging/124000000/123170000/123166200/123166125/e935fa7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Triple Room | Interior](https://images.trvl-media.com/lodging/124000000/123170000/123166200/123166125/6d80ec6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Triple Room | Desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/124000000/123170000/123166200/123166125/940c4785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Triple Room | Bathroom | Free toiletries, towels, soap, shampoo](https://images.trvl-media.com/lodging/124000000/123170000/123166200/123166125/08ce5fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homestay In Boston - [](https://www.expedia.com/Boston-Hotels-Homestay-In-Boston.h123166125.Hotel-Information) Dorchester 8.4/10 Very Good (16 reviews) "The property was very clean and well maintained with spacious showers and a tv in your room. There are fresh towels as well as a free continental breakfast. The location has many restaurants/convenient stores not far away as well. Definitely recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler $61 nightly $71 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Homestay-In-Boston.h123166125.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/124000000/123090000/123086900/123086868/w987h712x22y16-3f0ec4ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, soap, shampoo, toilet paper](https://images.trvl-media.com/lodging/124000000/123090000/123086900/123086868/b7731ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123090000/123086900/123086868/62a060c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/124000000/123090000/123086900/123086868/w987h712x22y16-40401b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homestay Near Downtown Boston [](https://www.expedia.com/Boston-Hotels-Homestay-Near-Downtown-Boston.h123086868.Hotel-Information) Dorchester 9.0/10 Wonderful (7 reviews) "Very clean, big rooms. Great breakfast options as well. For someone who just wants a home away from home, this is the place! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zakir $72 nightly $83 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Homestay-Near-Downtown-Boston.h123086868.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145268/9e8a5760.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145268/7eb70e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145268/92cc92c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Ensuite (Two Full Beds) | Free WiFi](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145268/f350449a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The College Club of Boston [](https://www.expedia.com/Boston-Hotels-The-College-Club-Of-Boston.h1145268.Hotel-Information) Back Bay 9.4/10 Exceptional (1,004 reviews) "Outstanding location, pleasant facilities and staff, decent breakfast choices. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary $169 nightly $194 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-College-Club-Of-Boston.h1145268.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/33110329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/f9d27d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/46c702a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/441c3014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Pistachio Room at TPH - Boston [](https://www.expedia.com/Boston-Hotels-The-Pistachio-Room.h51876423.Hotel-Information) Brighton 9.6/10 Exceptional (62 reviews) "Great location and wonderful host" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert M. $150 nightly $172 total Feb 6 - Feb 7 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Pistachio-Room.h51876423.Hotel-Information) ![King Luxury Suite Overlooking the Bay | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/390d6f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Luxury Suite Overlooking the Bay | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/021114f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/dadfe6c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite w/ Hot Tub and Fireplace | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/907b6e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Beacon Waterfront Inn [](https://www.expedia.com/Boston-Hotels-The-Beacon-Waterfront-Inn.h12363414.Hotel-Information) Hull 9.4/10 Exceptional (305 reviews) "The room was perfect, the house was perfect. The continental breakfast was poor. Oatmeal, Grits, pancakes, fresh fruit, banana " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chisulo $149 nightly $166 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Beacon-Waterfront-Inn.h12363414.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/980000/977400/977322/fc9d6dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/1000000/980000/977400/977322/3466e8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/980000/977400/977322/ccd05b4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/980000/977400/977322/63339218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Irving House At Harvard [](https://www.expedia.com/Boston-Hotels-Irving-House-At-Harvard.h977322.Hotel-Information) Mid-Cambridge 9.0/10 Wonderful (1,000 reviews) "Staff still worked and fed us through a huge snow storm. Really appreciated that" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keoki $155 nightly $177 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Irving-House-At-Harvard.h977322.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/46000000/45020000/45019700/45019626/cf80a236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/46000000/45020000/45019700/45019626/48f965fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/46000000/45020000/45019700/45019626/49c793d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/46000000/45020000/45019700/45019626/e789a859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Daniels House Inn [](https://www.expedia.com/Boston-Hotels-Daniels-House.h45019626.Hotel-Information) Salem 9.4/10 Exceptional (101 reviews) "Clearly a well managed historic inn. Gorgeous, comfortable, unique, in a very walkable area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) April $208 nightly $208 total Feb 11 - Feb 12 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Daniels-House.h45019626.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/w2000h2936x0y64-1c599ade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily cooked-to-order breakfast](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/241e8c87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/84639258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/29b4f786.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Salem Inn [](https://www.expedia.com/Boston-Hotels-The-Salem-Inn.h10270.Hotel-Information) Salem 9.2/10 Wonderful (1,000 reviews) "This place was great. We loved our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jared $180 nightly $201 total Feb 6 - Feb 7 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Salem-Inn.h10270.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153660/c56c123e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153660/033f0b58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153660/df4209be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153660/585b10da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Bridge Inn [](https://www.expedia.com/Boston-Hotels-North-Bridge-Inn.h1153660.Hotel-Information) Concord 8.4/10 Very Good (349 reviews) "Hot breakfast, attentive staff, proximity to a lot of history including Boston" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martin $195 nightly $218 total Feb 6 - Feb 7 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-North-Bridge-Inn.h1153660.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/109000000/108430000/108421900/108421852/e0abe334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108430000/108421900/108421852/c8337f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/109000000/108430000/108421900/108421852/f956d939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108430000/108421900/108421852/w1594h1074x167y6-37aa5c9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming B&B close to Salem and Boston [](https://www.expedia.com/Boston-Hotels-Charming-BB-Close-To-Salem-And-Boston.h108421852.Hotel-Information) Lynn 5.8/10 (16 reviews) "The stay was okay. The place was clean and had everything needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison M. $195 nightly $214 total Feb 28 - Mar 1 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Charming-BB-Close-To-Salem-And-Boston.h108421852.Hotel-Information) ![Basic Quadruple Room | Desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/126000000/125060000/125050200/125050198/8b3dd660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Double or Twin Room | Bathroom | Towels, soap, shampoo, toilet paper](https://images.trvl-media.com/lodging/126000000/125060000/125050200/125050198/dc4fbf84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Double or Twin Room | Interior](https://images.trvl-media.com/lodging/126000000/125060000/125050200/125050198/ebb85b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Double or Twin Room | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/126000000/125060000/125050200/125050198/5f07047f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homestay Near Near Savin Hill Area [](https://www.expedia.com/Boston-Hotels-Homestay-Near-Near-Savin-Hill-Area.h125050198.Hotel-Information) Dorchester 2.0/10 (1 review) "The guy change the house and location at an interval I didn't have no option. He kept sending encrypted access code for the check in. He masked to send ID to he's WhatsApp. He doesn't reply on time. I told him parking spot is important for me while there wasn't none at the place he changed me to. For very long waiting I was having the the obligation to find another place. When I try to reach out to him he even don't read the message. I don't recommend this hoster. It was a bad experience and a... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jules Andre $73 nightly $84 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Homestay-Near-Near-Savin-Hill-Area.h125050198.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=2026-02-19&endDate=2026-02-20®ionId=175481&adults=2&lodging=BED_AND_BREAKFAST&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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d175481-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d175481-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg) ### The Revolution Hotel 10/10 Excellent "Clean and courteous. Convenient and safe location. " [](https://expedia.com/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "Best price for the location! Always clean and great staff!" [](https://expedia.com/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Wonderful service, gorgeous room" [](https://expedia.com/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Beautiful hotel, excellent staff and really nice location." [](https://expedia.com/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "Clean room. Great staff!" [](https://expedia.com/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3_y.jpg) ### Omni Boston Hotel at the Seaport 10/10 Excellent "The room looked amazing and the staff was very nice" [](https://expedia.com/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg) ### citizenM Boston North Station 10/10 Excellent "The view and the room were perfect " [](https://expedia.com/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94_y.jpg) ### Hyatt Regency Boston 10/10 Excellent "Check-in was super easy and quick. Everything was really clean. And the gym and pool were both excellent and exceeded the expectations of the teen athletes I traveled with" [](https://expedia.com/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg) ### Omni Parker House 10/10 Excellent "The staff is wonderful. The updating of the hotel is beautiful!" [](https://expedia.com/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 3,529 | | ----------------- | ------ | | Accommodation | 29 B&B | | Lowest Price | $166 | | Highest Price | $218 | ## Frequently asked questions ### What is the nightly rate for a Bed and Breakfast in Winchester? ### When is the best time to book a Bed and Breakfast in Winchester? > April, in particular, is a fantastic month to visit. The temperatures typically range from the mid-40s to mid-70s Fahrenheit, creating a comfortable climate for sightseeing and outdoor adventures. You'll find the local flora in full bloom, enhancing the beauty of Winchester's famous landmarks, including the stunning Handley Regional Library and the historic Old Town. > > > If you're looking for a more budget-friendly time to visit, consider planning your trip in November. This month offers a quieter experience, allowing for intimate exploration of the town's attractions without the usual crowds. The autumn foliage adds a unique charm to the surroundings, making it a great time for scenic drives and photography. ### What is the difference between a Winchester B&B and a hotel? ## 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) - [Condo Rentals in Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Condos.d6209680-aaCondos.Travel-Guide-Accommodation) - [B&B in Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Bed-And-Breakfast.d6209680-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Hotels.d6209680.Travel-Guide-Hotels) - [Woburn Hotels ](https://www.expedia.com/Woburn-Hotels.d10373.Travel-Guide-Hotels) - [Apartments in Woburn ](https://www.expedia.com/Woburn-Apartments.d10373-aaApartments.Travel-Guide-Accommodation) - 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