Winchester hotels from HK$721

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Our top choices for Winchester hotels

Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.2 out of 10, Wonderful, (1,391 reviews)
"Decent hotel "
United States
Patricia
The price is HK$895
HK$1,000 total
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn Boston Woburn

Hilton Boston/Woburn

Hilton Boston/Woburn
3.5 star property
Woburn
8.6 out of 10, Excellent, (1,226 reviews)
"The staff was excellent and very friendly. The room and pool were great!"
United States
Elizabeth
The price is HK$955
HK$1,067 total
includes taxes & fees
27 Feb - 28 Feb
Hilton Boston/Woburn

Residence Inn by Marriott Boston Natick

Residence Inn by Marriott Boston Natick
3.0 star property
Natick
9.6 out of 10, Exceptional, (731 reviews)
"Yes, it was clean and the staff was very helpful and friendly. "
United States
karen
The price is HK$1,102
HK$1,231 total
includes taxes & fees
26 Feb - 27 Feb
Residence Inn by Marriott Boston Natick

Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
Watertown
9.4 out of 10, Exceptional, (1,009 reviews)
"Friendly staff, good free breakfast included!"
Canada
kennedy
The price is HK$932
HK$1,040 total
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn & Suites Watertown Boston

Hampton Inn Boston Bedford Burlington

Hampton Inn Boston Bedford Burlington
2.5 star property
Billerica
9.2 out of 10, Wonderful, (1,001 reviews)
"Nice place to stay "
United States
Stacey
The price is HK$698
HK$780 total
includes taxes & fees
6 Mar - 7 Mar
Hampton Inn Boston Bedford Burlington

Sheraton Boston Needham Hotel

Sheraton Boston Needham Hotel
3.5 star property
Needham
8.8 out of 10, Excellent, (1,571 reviews)
"wonderful, pet friendly (we came with a cat), clean, centrally located hotel! Truly enjoyed our stay. "
United States
Daniela
The price is HK$867
HK$969 total
includes taxes & fees
28 Feb - 1 Mar
Sheraton Boston Needham Hotel

The Whitney Hotel

The Whitney Hotel
4.0 star property
Beacon Hill
9.6 out of 10, Exceptional, (520 reviews)
"Our second stay there, love it"
United States
Steve
The price is HK$2,412
HK$2,809 total
includes taxes & fees
8 Mar - 9 Mar
The Whitney Hotel

Arcadian Hotel

Arcadian Hotel
3.5 star property
Coolidge Corner
8.0 out of 10, Very good, (3,906 reviews)
"Staff was courteous, hotel was in a good location "
United States
Jill
The price is HK$891
HK$1,257 total
includes taxes & fees
1 Mar - 2 Mar
Arcadian Hotel

Nantasket Beach Resort

Nantasket Beach Resort
3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1,006 reviews)
"Front desk staff was great"
United States
John
The price is HK$931
HK$1,223 total
includes taxes & fees
23 Feb - 24 Feb
Nantasket Beach Resort

Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington
4.0 star property
Burlington
9.8 out of 10, Exceptional, (1,002 reviews)
"Peaceful, clean, beautiful.friendly staffing Sure will go back "
United States
Marie
Archer Hotel Boston/Burlington

Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston
3.0 star property
Andover
9.0 out of 10, Wonderful, (1,014 reviews)
"Great staff and very good rooms. Great breakfast. "
United States
Albert
The price is HK$836
HK$934 total
includes taxes & fees
1 Mar - 2 Mar
Sonesta ES Suites Andover Boston

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End
3.0 star property
South End
9.0 out of 10, Wonderful, (1,009 reviews)
"Wonderful stay "
United States
Fernando
The price is HK$742
HK$1,092 total
includes taxes & fees
23 Feb - 24 Feb
Staypineapple, A Delightful Hotel, South End

Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree
3.5 star property
North Braintree
9.0 out of 10, Wonderful, (2,704 reviews)
"Clean room great breakfast, and super front desk staff"
United States
Mark
The price is HK$817
HK$912 total
includes taxes & fees
1 Mar - 2 Mar
Hyatt Place Boston/Braintree

Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham
3.0 star property
Waltham
8.8 out of 10, Excellent, (1,003 reviews)
"The room was nice and clean and the staff were great. "
United States
Kristy
The price is HK$681
HK$761 total
includes taxes & fees
26 Feb - 27 Feb
Hilton Garden Inn Boston/Waltham

Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
7.6 out of 10, Good, (2,331 reviews)
"Another great stay!"
United States
Brian
Lakeside Inn

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, (2,014 reviews)
"Perfect stay. "
United States
Alyssa
The price is HK$774
HK$864 total
includes taxes & fees
5 Mar - 6 Mar
La Quinta Inn & Suites by Wyndham Boston-Andover

HYATT house Boston/Waltham

HYATT house Boston/Waltham
3.0 star property
Waltham
8.8 out of 10, Excellent, (1,099 reviews)
"Super clean and quiet, friendly staff, convenient location"
United States
Taylor
The price is HK$828
HK$925 total
includes taxes & fees
8 Mar - 9 Mar
HYATT house Boston/Waltham

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
3.0 star property
Spring Hill
9.6 out of 10, Exceptional, (1,011 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 HK$1,119
HK$1,250 total
includes taxes & fees
22 Mar - 23 Mar
Cambria Hotel Boston Somerville

Hotel 1868

Hotel 1868
3.5 star property
Agassiz
9.6 out of 10, Exceptional, (1,004 reviews)
"Loved the room and the service! "
United States
Tracie
The price is HK$951
HK$1,102 total
includes taxes & fees
4 Mar - 5 Mar
Hotel 1868

Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham
3.0 star property
Waltham
9.4 out of 10, Exceptional, (1,650 reviews)
"The room, facilities and staff were great."
United States
Michael
The price is HK$657
HK$734 total
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn & Suites Boston/Waltham
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

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Charming Neighbourhoods: Explore the picturesque areas of Central Winchester and the historic streets of Beacon Hill, offering a unique character and welcoming atmosphere.
  • Cultural Experiences: Engage with art galleries and significant historic sites, perfect for those seeking a rich cultural experience.
  • Outdoor Activities: Enjoy a variety of outdoor pursuits in urban parks, ideal for families and outdoor enthusiasts.
  • Diverse Accommodation: Choose from a range of lodging options, including charming bed and breakfasts and pet-friendly hotels.
  • Proximity to Boston: Benefit from easy access to the vibrant atmosphere of Boston City, just a short distance away.

Find great hotels near Winchester

Discover a range of delightful accommodation options in Winchester, Massachusetts, catering to various needs and budgets. Whether you're seeking a comfortable hotel for business travel, a charming bed and breakfast, or pet-friendly lodgings, Winchester has it all. Enjoy a welcoming atmosphere for LGBTQIA travellers and explore affordable stays that ensure a pleasant experience during your visit to this picturesque town.

  • citizenM Boston North Station: This modern 4-star hotel is a vibrant choice for the discerning traveller seeking a blend of style and functionality. Located 11.3km from Winchester, citizenM Boston North Station embraces a sophisticated, tech-savvy atmosphere with its contemporary design and innovative amenities. The hotel offers comfortable, compact rooms that feature mood lighting and oversized beds, perfect for both business and leisure. Its commitment to inclusivity makes it a welcoming space for the LGBTQIA community, ensuring a memorable and supportive stay.
  • Hyatt Regency Boston/Cambridge: Situated 11.3km from Winchester, this 4-star hotel stands out for its pet-friendly policies and exceptional hospitality. The Hyatt Regency Boston/Cambridge combines modern luxury with thoughtful amenities, such as spacious rooms equipped with all the essentials for business travellers. The hotel is particularly welcoming to pets, allowing dogs with specific policies in place, making it a great choice for pet owners. Additionally, its affiliation with LGBTQI travel guides highlights its commitment to inclusivity, providing a warm environment for all guests.
  • Lakeside Inn: Located 8.0km from Winchester, Lakeside Inn offers a serene escape for business travellers seeking comfort and convenience. This charming accommodation features a tranquil setting with easy access to local attractions. Guests appreciate the friendly staff and well-appointed rooms, which create a relaxing atmosphere after a busy day. With its focus on providing a peaceful retreat, Lakeside Inn is an ideal choice for those looking to unwind while still being close to the vibrant offerings of the Winchester area.

Where to stay in Winchester

Winchester, Massachusetts, offers a delightful blend of charm and urban vibrancy, making it perfect for families and outdoor enthusiasts. Explore the historic streets of Beacon Hill and the bustling atmosphere of Boston City, just a short distance away. Enjoy the calmer vibes of Central Winchester, where friendly locals and picturesque surroundings create a welcoming experience. Discover the unique character of this charming city and its surrounding neighbourhoods, ideal for a memorable vacation.

  • Boston: As a bustling metropolis, Boston is a rich tapestry of history and modernity, making it an exciting destination for travellers. Situated a short distance from Winchester, the city boasts a variety of cultural experiences, from historic landmarks like Fenway Park and Boston Common to vibrant shopping districts. Peak visitor times in the summer and autumn months bring lively city-themed events and concerts. With its renowned universities and educational institutions, Boston is also a hub for knowledge-seekers. Be sure to explore the Freedom Trail, a 4.0km route that showcases significant historical sites.
  • Cambridge: Located approximately 9.7km from Winchester, Cambridge is known for its prestigious universities, including Harvard and MIT. This city draws visitors year-round for its vibrant academic atmosphere and family-friendly attractions. The peak travel seasons in the spring and summer see many enjoying the city's rich cultural offerings, including museums, galleries, and local shops. The bustling squares and scenic parks provide a perfect backdrop for leisurely exploration. Don’t miss the chance to stroll along the Charles River or indulge in the eclectic dining scene.
  • Woburn: Just 3.2km from Winchester, Woburn is a charming city that offers a blend of family-friendly activities and business amenities. Visitors are drawn to Woburn for its shopping centres and local parks, making it a great spot for leisurely afternoons. The city sees consistent traveller interest throughout the year, with peaks in the spring and summer months. Woburn is also home to historic sites and venues that host various events, ensuring a vibrant community atmosphere. Take time to explore the local dining options and enjoy the welcoming spirit of this quaint city.

Things to do near Winchester

Winchester, Massachusetts, is an ideal destination for family, outdoor, and city-themed holidays. Visitors can explore art galleries, enjoy exhilarating activities for an adrenaline rush, and partake in family outings. The area also boasts shopping centres and malls, providing ample opportunities for retail therapy. With its blend of educational experiences and leisure activities, Winchester promises a delightful experience for all ages.

Shopping

For a delightful shopping experience, visit Harvard Square, located 9.7km from Winchester, offering a vibrant atmosphere. Quincy Market is 12.9km away, perfect for family outings. If you're up for a drive, Assembly Row is 8.0km away, providing diverse shopping options for all.

Recreation

MGM Music Hall at Fenway, located 12.9km from Winchester, offers a vibrant atmosphere filled with live performances, perfect for immersing yourself in music and culture. Similarly, Boston Symphony Hall, also 12.9km away, provides an elegant setting for enjoying classical concerts, while Leader Bank Pavilion, 14.5km distant, features a lively waterfront experience with various shows.

Adventure

Explore the Independence Greenway Bike Route, a scenic hiking trail located 16.1km from Winchester, perfect for outdoor enthusiasts seeking adventure. Visit Horn Pond, situated 3.2km away, for a refreshing escape into nature. For water sports, head to the Courageous Sailing Center, 11.3km from Winchester, embracing thrilling outdoor activities.

Nightlife

Experience the vibrant nightlife in Winchester by visiting Woburn Bowladrome, an exciting arcade adventure zone just 3.2km away. For a romantic evening, head to Cambridge Common, a charming pub 8.0km away, or enjoy a cultural night at Somerville Theatre, located 6.4km from Winchester.

*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, particularly on Sundays. Use Expedia's search tool to filter results by budget and hotel type, including eco-certified options. Combining your hotel, flights, and activities into a package can also yield significant savings. For transport, utilise the local public transit system, which is budget-friendly. Additionally, look for free activities and local parks to enjoy without spending much, ensuring a delightful yet economical experience in Winchester.

  • 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: Expedia's search tool enables you to specify your budget, preferred location, and additional criteria. You can organise your search results to display prices from lowest to highest, allowing you to easily find the most affordable hotels. Furthermore, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Winchester with your flights and activities by opting for an Expedia package.

Find the best attractions near Winchester

Winchester, Massachusetts, offers a delightful blend of outdoor activities and cultural experiences, making it ideal for family vacations. Visitors can explore urban parks, historic colleges and universities, and significant historic sites. The attractions cater to those seeking a rich cultural experience while providing ample opportunities for family enjoyment in a charming city setting.

  • Fenway Park: Experience the rich history and vibrant atmosphere of one of America's oldest ballparks. Home to the Boston Red Sox, this iconic stadium offers a unique glimpse into American sports culture, with its famous Green Monster and passionate fans.
  • Harvard University: Explore the prestigious grounds of the world-renowned Harvard University. With its stunning architecture and rich academic heritage, visitors can stroll through picturesque courtyards and soak in the intellectual vibes that permeate this historic campus.
  • TD Garden: Attend a thrilling event at TD Garden, Boston's premier venue for sports and entertainment. Known for its modern facilities and lively atmosphere, it hosts everything from basketball games to concerts, making it a hub of business and leisure activity.

Best time to go to Winchester

The best time to visit Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winchester falls in January, 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

Winchester, Massachusetts, is conveniently accessible via several major airports. BOSton Logan International Airport (BOS) is situated 14.5km away and offers luxurious hotel options such as Encore Boston Harbor, InterContinental Boston, and Boston Harbor Hotel, all within 4.8km of the airport. Providence T.F. Green Airport (PVD) is 54.8km away, with notable accommodations like Omni Providence Hotel and Hotel Providence, both 11.3km from the airport. Additionally, Manchester-Boston Regional Airport (MHT) is 57.9km distant, featuring The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, each just 6.4km from the airport, ensuring a comfortable stay for visitors.

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 traveller data. Two other options for your stay in the area are The Revolution Hotel and The Langham, Boston. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino: This holiday home rental outside of Winchester is located on the waterfront, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, most hotel bookings are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What are some accommodation options with pools in Winchester?
The Langham, Boston: Hotel, 4-minute walk from Boston Harbor. Provides a sauna, an indoor pool and complimentary high-speed (wired) Internet access. Omni Boston Hotel at the Seaport and Seaport Hotel Boston are two additional hotels with an on-site 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 football matches and lake views. Fenway Park, Encore Boston Harbor and TD Garden are some of the top sights around the area. In Winchester, there are 5 hotels and other accommodation options to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
A couple of favourite places to visit are Winter Pond and Middlesex Fells Reservation. Additionally, you'll find Fenway Park and Encore Boston Harbor in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.
How can I get around Winchester?
To venture out into 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 temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 13 cm of snowfall.

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