Winchester Hotels

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Our top choices for Winchester hotels

Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.0 out of 10, Wonderful, (1,371 reviews)
"Very good room and great breakfast!"
United States
Rodrigo
The price is P6,123
P6,839 total
includes taxes & fees
Feb 6 - Feb 7
Hampton Inn Boston Woburn

Best Western Plus New Englander

Best Western Plus New Englander
2.5 star property
Woburn
8.6 out of 10, Excellent, (1,004 reviews)
"Clean room, great and attentive staff, good breakfast !"
United States
Adriana
The price is P5,232
P5,845 total
includes taxes & fees
Jan 14 - Jan 15
Best Western Plus New Englander

Sheraton Boston Needham Hotel

Sheraton Boston Needham Hotel
3.5 star property
Needham
8.8 out of 10, Excellent, (1,535 reviews)
"Comfortable bed, quiet and great staff"
United States
Shauna
The price is P5,534
P6,182 total
includes taxes & fees
Feb 1 - Feb 2
Sheraton Boston Needham Hotel

Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
Watertown
9.4 out of 10, Exceptional, (1,003 reviews)
"The environment was nice, the room felt new, and the breakfast was very nice. We really enjoyed our stay."
Canada
Jing
The price is P6,268
P7,002 total
includes taxes & fees
Jan 18 - Jan 19
Hampton Inn & Suites Watertown Boston

Nantasket Beach Resort

Nantasket Beach Resort
3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1,002 reviews)
"Great room off season, great view of the ocean. Have stayed before and will be back!"
United States
Patricia
The price is P6,577
P8,730 total
includes taxes & fees
Jan 25 - Jan 26
Nantasket Beach Resort

Hilton Garden Inn Boston Brookline, MA

Hilton Garden Inn Boston Brookline, MA
3.0 star property
Brookline
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean, convenient location."
United States
Tony
The price is P8,000
P8,935 total
includes taxes & fees
Jan 25 - Jan 26
Hilton Garden Inn Boston Brookline, MA

Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston
2.5 star property
Andover
8.8 out of 10, Excellent, (1,002 reviews)
"The nicest hotel in the area. "
United States
Edna
The price is P6,755
P7,546 total
includes taxes & fees
Jan 19 - Jan 20
Sonesta ES Suites Andover Boston

The Whitney Hotel

The Whitney Hotel
4.0 star property
Beacon Hill
9.6 out of 10, Exceptional, (501 reviews)
"Our second stay there, love it"
United States
Steve
The price is P16,141
P18,796 total
includes taxes & fees
Jan 26 - Jan 27
The Whitney Hotel

The Arcadian Hotel

The Arcadian Hotel
3.5 star property
Brookline
8.0 out of 10, Very Good, (3,880 reviews)
"Great Hotel"
United States
Naika
The price is P5,504
P8,134 total
includes taxes & fees
Jan 16 - Jan 17
The Arcadian Hotel

Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG
2.5 star property
Chelmsford
8.8 out of 10, Excellent, (1,003 reviews)
"Great place to stay comfortably "
United States
Rene
The price is P6,274
P7,008 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Chelmsford by IHG

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End
3.0 star property
South End
9.0 out of 10, Wonderful, (1,001 reviews)
"Friendly and helpful staff, clean hotel and cute decor. Also, a great bar downstairs! "
Canada
Jasmyn
The price is P3,676
P6,000 total
includes taxes & fees
Feb 1 - Feb 2
Staypineapple, A Delightful Hotel, South End

La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover
3.0 star property
Andover
8.2 out of 10, Very Good, (1,972 reviews)
"Nice room, free breakfast, staff very joyful "
United States
Kai
The price is P5,867
P6,553 total
includes taxes & fees
Feb 1 - Feb 2
La Quinta Inn & Suites by Wyndham Boston-Andover

Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
7.6 out of 10, Good, (2,326 reviews)
"Another great stay!"
United States
Brian
Lakeside Inn

Hyatt Place Boston/Medford

Hyatt Place Boston/Medford
3.0 star property
Medford
8.4 out of 10, Very Good, (1,614 reviews)
"Amazing stay and friendly staff! "
United States
Caterin
The price is P6,511
P7,273 total
includes taxes & fees
Jan 17 - Jan 18
Hyatt Place Boston/Medford

Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham
3.0 star property
Waltham
8.8 out of 10, Excellent, (1,003 reviews)
"Very clean room, quiet, we got the items we needed and had a very comfortable stay for the weekend!"
United States
Alison
The price is P4,325
P4,831 total
includes taxes & fees
Jan 16 - Jan 17
Hilton Garden Inn Boston/Waltham

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
3.0 star property
Spring Hill
9.6 out of 10, Exceptional, (1,003 reviews)
"Amazing hotel! Cozy lobby, friendly and helpful staff, clean and spacious room, valet parking. All around great stay!"
United States
Sandra
The price is P7,529
P8,410 total
includes taxes & fees
Feb 8 - Feb 9
Cambria Hotel Boston Somerville

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
2.5 star property
Chelsea
9.0 out of 10, Wonderful, (1,001 reviews)
"Very friendly staff and close to everything I wanted to see"
United States
Rachel ann
The price is P5,987
P6,688 total
includes taxes & fees
Jan 18 - Jan 19
Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

Hotel 1868

Hotel 1868
3.5 star property
Agassiz
9.6 out of 10, Exceptional, (1,001 reviews)
"Clean rooms, great gym, friendly and helpful staff."
United States
Jose
The price is P5,841
P6,773 total
includes taxes & fees
Jan 18 - Jan 19
Hotel 1868

Porter Square Hotel

Porter Square Hotel
3.0 star property
North Cambridge
9.2 out of 10, Wonderful, (1,002 reviews)
"This was a good place for a stay in a convenient location."
United States
Corey
The price is P5,841
P6,773 total
includes taxes & fees
Jan 18 - Jan 19
Porter Square Hotel

Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington
2.0 star property
Burlington
9.0 out of 10, Wonderful, (158 reviews)
"Good rooms, helpful staff"
United States
Abhir
The price is P5,623
P6,281 total
includes taxes & fees
Jan 16 - Jan 17
Sonesta Simply Suites Boston Burlington
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.
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Stay near popular Winchester attractions

Learn more about Winchester

Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails.

Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA.

Top Winchester Hotel Reviews

More cheap stays in Winchester

Find out more about Winchester

Top reasons to visit Winchester

  • Charming Streets: Stroll through the picturesque streets of Winchester, where friendly locals create a welcoming atmosphere.
  • Historical Attractions: Explore significant historical sites and nearby cities, immersing yourself in rich local heritage.
  • Urban Parks: Enjoy leisurely walks in serene parks, perfect for relaxation and appreciating nature.
  • Diverse Accommodation: Choose from a variety of charming hotels and bed & breakfasts, catering to all types of travellers.
  • Entertainment Options: Indulge in local shopping centres, a movie theatre, and event venues for lively entertainment.

Find great hotels near Winchester

Discover the charming accommodation options in Winchester, Massachusetts, where a variety of hotels and bed & breakfasts await your arrival. Whether you're seeking a pet-friendly stay, a welcoming atmosphere for LGBTQIA travellers, or business-oriented facilities, Winchester offers a delightful selection of top-rated hotels. With exceptional reviews and diverse lodging types, you're sure to find the perfect base for your American adventure.

  • citizenM Boston North Station: Emphasising a modern and vibrant atmosphere, citizenM Boston North Station is an ideal choice for savvy travellers seeking a blend of business and leisure. This 4-star hotel boasts stylish, tech-savvy rooms designed for ultimate comfort, with amenities including free Wi-Fi, smart TVs, and mood lighting. Its LGBTQIA-friendly environment ensures a welcoming experience for all guests. Located a mere 11.3km from Winchester, this hotel also offers easy access to Boston’s bustling attractions and business districts, making it perfect for both work and play.
  • Hyatt Regency Boston/Cambridge: A perfect blend of comfort and convenience, Hyatt Regency Boston/Cambridge is a 4-star hotel that caters to diverse travellers, including those with pets. With a pet-friendly policy and amenities such as a gym, business centre, and on-site dining, guests can enjoy a relaxed yet productive stay. The hotel embraces an LGBTQIA-friendly ethos, ensuring inclusivity for all. Situated 11.3km from Winchester, the hotel’s scenic views of the Charles River and proximity to Cambridge’s vibrant culture make it a superb choice for both leisure and business travellers.
  • Four Points by Sheraton Boston Newton: Ideal for those seeking a romantic getaway, Four Points by Sheraton Boston Newton offers a serene escape immersed in nature. This 3.5-star hotel features charming accommodations and a range of amenities, including an indoor pool and spa services, perfect for couples looking to unwind. With romance packages available, guests can indulge in a unique experience tailored to their needs. Just 11.3km from Winchester, the hotel’s tranquil setting and attentive staff ensure a memorable stay, making it a lovely choice for a romantic vacation.

Where to stay in Winchester

Winchester, Massachusetts, offers a delightful blend of charm and urban atmosphere, perfect for families and business travellers alike. Stroll through its picturesque streets, where friendly locals enhance the welcoming vibe. Explore nearby cities for a rich historical experience, or enjoy leisurely walks in the serene parks. With a variety of attractions within walking distance, your visit promises to be both enriching and enjoyable.

  • Boston: As a vibrant metropolis, Boston is the heart of Massachusetts, brimming with culture and history. Situated a short distance from Winchester, it attracts visitors year-round, with peak arrivals during the summer months and October. Known for its rich educational landscape, Boston is home to renowned universities and historic landmarks. You can immerse yourself in an array of activities including music concerts, shopping at bustling malls, and exploring historic sports stadiums. The city's unique blend of historic charm and modern amenities creates an enticing travel experience, making it a must-visit destination.
  • Cambridge: Located approximately 9.7km from Winchester, Cambridge is a city that exudes an intellectual aura, largely due to its prestigious universities. With a steady influx of tourists, particularly in the spring and summer, it offers a family-friendly atmosphere alongside rich cultural experiences. Visitors can enjoy a vibrant shopping scene, with various centres and local boutiques. The presence of historic universities and sports venues adds to the city's allure, ensuring that there's always something interesting to explore, whether you're wandering along the scenic Charles River or indulging in local cuisine.
  • Woburn: Just 3.2km from Winchester, Woburn is a charming city that welcomes families and business travellers alike. While its visitor numbers remain consistent throughout the year, the city sees a surge in activity during the warmer months. Woburn offers a delightful mix of shopping centres and educational venues, making it an ideal spot for leisurely explorations. It is also home to historic landmarks and event venues, which enrich the local experience. With its close proximity to both Boston and Cambridge, Woburn serves as a convenient base for exploring the rich history and culture of the Greater Boston area.

Things to do near Winchester

Winchester, Massachusetts, offers a delightful blend of activities for city-themed, family, and business vacations. Visitors can enjoy educational attractions, explore local shopping centres, and indulge in a variety of entertainment options, including a movie theatre and event venues. Whether you're seeking leisure or vibrant social experiences, Winchester presents a charming backdrop for a memorable stay.

Shopping

In Winchester, you can enjoy shopping at Bow Market, just 8.0km away, offering a delightful mix of local businesses. Harvard Square, located 9.7km away, features a vibrant atmosphere with entertainment options. If you're up for a drive, the Boston Public Market is 11.3km away, showcasing local produce and crafts.

Recreation

Experience the vibrant atmosphere at MGM Music Hall at Fenway, where live music fills the air, just 12.9km from Winchester. For sports enthusiasts, Nickerson Field offers thrilling events 11.3km away, while the Paradise Rock Club, also 11.3km from Winchester, promises unforgettable concerts in an intimate setting.

Adventure

Explore Horn Pond, located 3.2km from Winchester, for a serene outdoor experience with scenic trails and nature. For water sports, head to Courageous Sailing Center, 11.3km away, where adventure awaits on the water. Alternatively, enjoy thrills at Boston Paintball, also 11.3km from Winchester.

Nightlife

In Winchester, LEGOLAND® Discovery Center provides a fun-filled family atmosphere with exciting arcade games just 8.0km away. Meanwhile, Somerville Theatre offers a romantic cultural experience 6.4km away, while Cambridge Common combines entertainment and romance in a charming pub setting, also 8.0km distant.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchester

To save money during your visit to Winchester, consider travelling between December and February, when accommodation prices are lower. Sundays typically offer the best rates, while Saturdays are the priciest. Utilise Expedia’s search tool to find budget-friendly options and combine your hotel, flights, and activities for additional savings. For public transport, take advantage of affordable options, and explore free activities in the area to maximise your experience without overspending.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchester is Sunday. The most expensive day to stay in Winchester is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can enjoy significant savings by combining your hotel reservations in Winchester with your flights and activities through an Expedia package.

Find the best attractions near Winchester

Winchester, Massachusetts, is an ideal destination for city-themed, family, and business holidays. Visitors can explore a variety of attractions, including urban parks, historic colleges and universities, and significant historical sites. This charming locale offers a delightful blend of cultural experiences and urban adventures, ensuring that travellers seeking family-friendly activities and rich history will find plenty to enjoy during their stay.

  • Fenway Park: Experience the rich history and vibrant atmosphere of Fenway Park, the iconic baseball stadium known for its passionate fans and classic charm. With its unique features like the Green Monster, it offers an unforgettable sports culture experience.
  • Harvard University: Wander through the historic campus of Harvard University, where academic excellence and cultural heritage converge. Its stunning architecture and rich history provide a captivating glimpse into one of the world’s most prestigious institutions.
  • Boston Common: Enjoy the expansive greenery of Boston Common, the oldest city park in the United States. Ideal for families, it offers recreational activities, scenic walks, and a lively urban atmosphere, perfect for relaxation amidst the bustling city.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.6°F (-1.9°C)Light RainMostly SunnyAverageSlightly Low
February29.8°F (-1.2°C)Light RainMostly CloudySlightly LowSlightly Low
March36.9°F (2.7°C)Light RainMostly SunnyAverageAverage
April47.7°F (8.7°C)Light RainMostly SunnySlightly HighAverage
May58.3°F (14.6°C)Light RainMostly SunnyAverageSlightly High
June66.4°F (19.1°C)Light RainMostly SunnyAverageAverage
July73.6°F (23.1°C)Light RainMostly SunnySlightly HighAverage
August72.3°F (22.4°C)Light RainMostly SunnyAverageAverage
September65.3°F (18.5°C)Light RainMostly SunnySlightly HighSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage
December35.1°F (1.7°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Winchester

To reach Winchester, Massachusetts, consider flying into one of three major airports. Boston Logan International Airport (BOS) is situated 14.5km away, with excellent nearby hotels such as the InterContinental Boston, Encore Boston Harbor, and Boston Harbor Hotel, all within 4.8km. Providence T.F. Green Airport (PVD) is 54.8km distant, with options like the Omni Providence Hotel and Hotel Providence, both 11.3km from the airport. Alternatively, Manchester-Boston Regional Airport (MHT) is 57.9km from Winchester, offering hotels like the DoubleTree by Hilton Manchester Downtown and EVEN Hotels Manchester Airport, conveniently located 4 and 3.2km away respectively.

Frequently asked questions

What's the best place to stay in Winchester?
Located 7.7 mi (12.4 km) from the heart of Winchester, Harborside Inn Of Boston is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Hilton Boston Back Bay and Omni Boston Hotel at the Seaport. See all available top hotels, or vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! You'll find that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What are some accommodations with pools in Winchester?
Omni Boston Hotel at the Seaport: Hotel, 3-minute walk from Boston Convention and Exhibition Center. Provides 4 restaurants, an outdoor pool, and a full-service spa. Seaport Hotel Boston and The Langham, Boston are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors can enjoy all that Winchester has to offer including the soccer matches and lake views. TD Garden, Fenway Park, and Encore Boston Harbor are some of the top sights around the area. In Winchester, there are 5 hotels and other accommodations to choose from. Find out more about Winchester.
What are the top places to visit in Winchester?
A couple of favorite places to visit are Winter Pond and Middlesex Fells Reservation. Additionally, you'll find TD Garden and Fenway Park in the area. Check out what more to see and do in Expedia's Winchester guide.
How should I get around Winchester?
To see more of the surrounding area, ride one of the trains from Winchester Station or Winchester Wedgemere Station. If you want to venture out around the area, you may want a rental car in Winchester for your journey.
What's the weather like in Winchester?
The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.

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