Title: Winchester Travel Guide: Best of Winchester, Boston Travel 2026 | Expedia.co.uk [Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Holiday Rentals in Winchester](https://expedia.co.uk/Winchester-Holiday-Rentals.d175481.Travel-Guide-HolidayRentals)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d175481.Car-Hire-Guide)[Winchester Holidays](https://expedia.co.uk/Winchester.d175481.Holidays-City-Breaks) # Winchester Travel Guide ## Tourist Guide ## Visit Winchester Things to do - Top hotels in Winchester - Top Holiday Rentals in Winchester ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Harborside Inn Of Boston 185 State St Boston MA £93 14 Jan - 15 Jan includes taxes & fees Stay at this hotel in Boston. Enjoy free Wi-Fi, a 24-hour front desk and a business centre. Our guests praise the breakfast and the restaurant in their reviews. ... 9.2/10 Wonderful! (6,125 reviews) everything was great! Reviewed on 8 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=14%2F01%2F2026&endDate=15%2F01%2F2026&selected=202814&PinnedHotelID=202814&HadPinnedHotel=true®ionId=175481) ![Hilton Boston Back Bay](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Boston Back Bay 40 Dalton St Boston MA £125 18 Jan - 19 Jan includes taxes & fees Stay at this business-friendly hotel in Boston. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the helpful staff and the clean rooms ... 8.4/10 Very Good! (1,245 reviews) Great breakfast, comfortable rooms. Reviewed on 7 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=5928&PinnedHotelID=5928&HadPinnedHotel=true®ionId=175481) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Omni Boston Hotel at the Seaport 450 Summer Street Boston MA £166 25 Jan - 26 Jan includes taxes & fees Stay at this luxury hotel in Boston. Enjoy free Wi-Fi, a full-service spa and 4 restaurants. Our guests praise the breakfast and the pool in their reviews. Popular ... 9/10 Wonderful! (4,390 reviews) Spotless rooms Reviewed on 5 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=68014393&PinnedHotelID=68014393&HadPinnedHotel=true®ionId=175481) [See all 3,972 properties in Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=13%2F01%2F2026&endDate=14%2F01%2F2026®ionId=175481) 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. ![Maverick Suites at 28 Fenway](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/aa77b438_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Maverick Suites at 28 Fenway 28 Fenway Boston MA Stay at this apartment in Boston. Enjoy free Wi-Fi, laundry facilities and concierge services. Popular attractions Fenway Park and Copley Square are located ... 8.6/10 Excellent! (333 reviews) Amazing Reviewed on 1 Jan 2026 [](https://expedia.co.uk/Boston-Hotels-28-Fenway.h95348090.Hotel-Information) ![Global Luxury Suites Downtown Boston](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/eaf6c86d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Global Luxury Suites Downtown Boston 8 Harrison Ave Boston MA Stay at this business-friendly aparthotel in Boston. Enjoy free Wi-Fi, a 24-hour front desk and a 24-hour business centre. Our guests praise the helpful staff ... 7.8/10 Good! (639 reviews) The area around the property was excellent. It felt very safe and quiet, with plenty of shopping and dining options nearby. Everything was walkable, which made the stay very convenient. Parking was easy, and transportation access was great. Overall, a great location and an enjoyable stay. Reviewed on 1 Jan 2026 [](https://expedia.co.uk/Boston-Hotels-Global-Luxury-Suites-Downtown-Boston.h22788576.Hotel-Information) ![Temple Place Suites](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/5a1c0f00_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Temple Place Suites 29 Temple Place Boston MA Stay at this apartment in Boston. Enjoy free Wi-Fi, laundry facilities and cable TV channels. Popular attractions Boston Common and New England Aquarium are ... 7/10 Good! (329 reviews) Hospitality from the staff… easy check in close to everything… very quiet which I loved… Reviewed on 2 Jan 2026 [](https://expedia.co.uk/Boston-Hotels-Temple-Place-Suites.h45791512.Hotel-Information) [See all properties in Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=175481&sort=VACATION_RENTAL) 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. ## Check Winchester hotel availability [Tonight ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=175481&startDate=2026-01-12&endDate=2026-01-13)[12 Jan - 13 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=175481&startDate=2026-01-12&endDate=2026-01-13) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=175481&startDate=2026-01-13&endDate=2026-01-14)[13 Jan - 14 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=175481&startDate=2026-01-13&endDate=2026-01-14) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=175481&startDate=16%2F01%2F2026&endDate=18%2F01%2F2026)[16 Jan - 18 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=175481&startDate=16%2F01%2F2026&endDate=18%2F01%2F2026) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=175481&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026)[23 Jan - 25 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=175481&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026) ### Popular places to visit ![Fenway Park which includes a sporting event and night scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/20000/20987-Fenway-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fenway Park Catch a game or take a tour at one of America’s most historic and beloved ballparks. [](https://expedia.co.uk/Fenway-Park-FenwayKenmore.d6023384.Attraction) ![Boston Common which includes a skyscraper, landscape views and a park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21217-Boston-Common.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston Common The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind. [](https://expedia.co.uk/Boston-Common-Beacon-Hill.d507377.Attraction) ![TD Garden](https://mediaim.expedia.com/destination/9/38b782f49bb48608c7709e4119911823.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### TD Garden Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area. [](https://expedia.co.uk/TD-Garden-Boston.d6070137.Attraction) ![Harvard University showing a city and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21000-Harvard-University.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Harvard University Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States. [](https://expedia.co.uk/Harvard-University-Lower-Allston.d6034936.Attraction) ![Gillette Stadium](https://mediaim.expedia.com/destination/2/dbb8b23949ff195c0c2ca1207ea300cd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Gillette Stadium Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theatre scene and great live music. [](https://expedia.co.uk/Gillette-Stadium-Foxboro.d6034500.Attraction) ![New England Aquarium](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/476000/476046-New-England-Aquarium.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### New England Aquarium From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips. [](https://expedia.co.uk/New-England-Aquarium-North-End.d6070109.Attraction) ### Things to do ![Boston CityPASS: Admission to Top 4 Boston Attractions](https://mediaim.expedia.com/localexpert/173116/5d73576c-38be-4337-8351-c85e937f9492.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston CityPASS®: Admission to Top 4 Attractions £59 per adult **92%** of travellers recommend [](https://expedia.co.uk/things-to-do/boston-citypass-admission-to-top-4-attractions.a173116.activity-details) ![Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must must-visit. ](https://mediaim.expedia.com/localexpert/46312679/f4dc7e7e-3f89-44f1-8c94-790c64c45eec.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### View Boston Observation Deck Admission Tickets £25 per adult **88%** of travellers recommend [](https://expedia.co.uk/things-to-do/view-boston-observation-deck-admission-tickets.a46312679.activity-details) ![Go City: Boston All-Inclusive Pass with 45+ Attractions](https://mediaim.expedia.com/localexpert/173074/064eb1cc-eb4f-4535-bc3f-dbc4e50db8ab.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Go City: Boston All-Inclusive Pass with 45+ Attractions £62 per adult **80%** of travellers recommend [](https://expedia.co.uk/things-to-do/go-city-boston-all-inclusive-pass-with-45-attractions.a173074.activity-details) ![Go City: Boston Explorer Pass - Choose 2 to 5 Attractions](https://mediaim.expedia.com/localexpert/529890/611532ec-feb1-408b-b52f-8d2151831e85.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Go City: Boston Explorer Pass - Choose 2 to 5 Attractions £40 per adult **98%** of travellers recommend [](https://expedia.co.uk/things-to-do/go-city-boston-explorer-pass-choose-2-to-5-attractions.a529890.activity-details) ![Museum of Ice Cream Boston](https://mediaim.expedia.com/localexpert/49950918/c2f41df1-2f57-4d2d-a4e0-16005e6ed400.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Museum of Ice Cream Boston Admission Ticket £39 per adult [](https://expedia.co.uk/things-to-do/museum-of-ice-cream-boston-admission-ticket.a49950918.activity-details) ![LEGO Discovery Center Boston Admission Ticket](https://mediaim.expedia.com/localexpert/46690980/7775d4e4-1c05-45f5-9b4b-d14d33ae62cd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### LEGO Discovery Center Boston Admission Ticket £21 per adult [](https://expedia.co.uk/things-to-do/lego-discovery-center-boston-admission-ticket.a46690980.activity-details) [See all activities in Winchester](https://expedia.co.uk/Things-To-Do-In-Winchester.d175481.Travel-Guide-Activities) ## Cities near Winchester ![Photo by Ana Lei](https://mediaim.expedia.com/destination/2/01014204691cd7d5adfcea2142a4e378.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Medford ![Woburn showing an administrative building and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/151000/151811-Woburn.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Woburn ![Photo by RoadTrip NewEngland](https://mediaim.expedia.com/destination/2/9acd0638e84c4d037e5a00d45cec335d.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Arlington ![Photo by Ana Lei](https://mediaim.expedia.com/destination/2/17e78810f678d9ae5e084239d7b2d8c2.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Stoneham ## Explore a world of travel with Expedia - 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