A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

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Check prices for these dates

Tonight
25 Sept - 26 Sept
Tomorrow
26 Sept - 27 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

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Our top choices for Winchester hotels

1. Best Western Plus New Englander

Best Western Plus New Englander
Woburn
United States
Richard
NZ$293
includes taxes & fees
4 Oct - 5 Oct
Best Western Plus New Englander

2. Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
Woburn
United States
Pamela
NZ$298
includes taxes & fees
4 Oct - 5 Oct
Hampton Inn Boston Woburn

3. Holiday Inn Express Boston North-Woburn by IHG

Holiday Inn Express Boston North-Woburn by IHG
Woburn
United States
Greg
NZ$283
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Boston North-Woburn by IHG

4. Lakeside Inn

Lakeside Inn
Wakefield
United States
Ryan
NZ$242
includes taxes & fees
27 Sept - 28 Sept
Lakeside Inn

5. Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG
Saugus
United States
Kelly
NZ$317
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Boston - Saugus by IHG

6. Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington
Burlington
United States
Ryan
NZ$385
includes taxes & fees
27 Sept - 28 Sept
Archer Hotel Boston/Burlington

7. Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington
Burlington
United States
Manuel
NZ$264
includes taxes & fees
20 Oct - 21 Oct
Sonesta Simply Suites Boston Burlington

8. Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham
Waltham
United States
Christopher
NZ$249
includes taxes & fees
4 Oct - 5 Oct
Hampton Inn & Suites Boston/Waltham

9. Aloft by Marriott Lexington

Aloft by Marriott Lexington
North Lexington
United States
Jennifer
NZ$253
includes taxes & fees
25 Oct - 26 Oct
Aloft by Marriott Lexington

10. Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham
Waltham
United States
iram
NZ$270
includes taxes & fees
27 Sept - 28 Sept
Hilton Garden Inn Boston/Waltham

11. Embassy Suites by Hilton Boston Waltham

Embassy Suites by Hilton Boston Waltham
Waltham
United States
Wesly
NZ$270
includes taxes & fees
25 Oct - 26 Oct
Embassy Suites by Hilton Boston Waltham

12. Hotel 1868

Hotel 1868
Agassiz
United States
Margaret
NZ$390
includes taxes & fees
12 Oct - 13 Oct
Hotel 1868

13. Hampton Inn Boston Bedford Burlington

Hampton Inn Boston Bedford Burlington
Billerica
Canada
Natalie
NZ$322
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Boston Bedford Burlington

14. Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
Spring Hill
United States
Mary
NZ$450
includes taxes & fees
4 Oct - 5 Oct
Cambria Hotel Boston Somerville

15. The Inn on Arsenal

The Inn on Arsenal
Watertown
United States
SEMORA
NZ$220
includes taxes & fees
27 Sept - 28 Sept
The Inn on Arsenal

16. HYATT house Boston/Waltham

HYATT house Boston/Waltham
Waltham
United States
Sarah
NZ$299
includes taxes & fees
4 Oct - 5 Oct
HYATT house Boston/Waltham

17. Porter Square Hotel

Porter Square Hotel
Porter Square
United States
Gerardo
NZ$364
includes taxes & fees
25 Oct - 26 Oct
Porter Square Hotel

18. Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
Watertown
United States
Jose
NZ$434
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn & Suites Watertown Boston

19. enVision Hotel Boston Everett

enVision Hotel Boston Everett
Everett
United States
Janet
NZ$324
includes taxes & fees
26 Oct - 27 Oct
enVision Hotel Boston Everett

20. Sonesta Select Boston Danvers

Sonesta Select Boston Danvers
Danvers
United States
Ludim
NZ$317
includes taxes & fees
28 Sept - 29 Sept
Sonesta Select Boston Danvers
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Stay near popular Winchester attractions

Winter Pond

9.0/10 (2 reviews)
Winter Pond offers a tranquil escape as Massachusetts' northernmost Coastal Plain Pondshore Community. Bring binoculars to spot diverse bird species while strolling along its peaceful shores.
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Griffin Photography Museum

Enjoy an outing to Griffin Photography Museum during your stay in Winchester. While you're in the area, wander around the natural setting.
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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.

See all hotels in Winchester
A historic building with a clock tower, red brick walls, and a green roof.

Top Winchester Hotel Reviews

Recent Reviews in Winchester

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Clean room"
Melvin 2-night trip
Posted 6 hours ago
Encore Boston Harbor
The Westin Boston Seaport District

The Westin Boston Seaport District

10/10 Excellent
"Great stay, always enjoy my time in Boston."
MATTHEW 1-night trip
Posted 8 hours ago
The Westin Boston Seaport District
citizenM Boston Back Bay

citizenM Boston Back Bay

10/10 Excellent
"Clean room, easy check in from a late flight"
dhimant 2-night trip
Posted 10 hours ago
citizenM Boston Back Bay
citizenM Boston North Station

citizenM Boston North Station

10/10 Excellent
"Very clean and great location! Staff weee amazing!"
Tiffany 3-night trip
Posted 13 hours ago
citizenM Boston North Station
Hilton Boston Park Plaza

Hilton Boston Park Plaza

8/10 Good
"Rooms are on small side but overall great location and friendly staff."
Lesley 1-night trip
Posted 17 hours ago
Hilton Boston Park Plaza

More cheap accommodation in Winchester

Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

1668 Worcester Rd Framingham MA
NZ$170
29 Sept - 30 Sept
includes taxes & fees
Motel 6 Framingham, MA - Boston West
The Inn on Arsenal

The Inn on Arsenal

100 N Beacon St Watertown MA
NZ$220
27 Sept - 28 Sept
includes taxes & fees
The Inn on Arsenal
Lakeside Inn

Lakeside Inn

595 North Ave Wakefield MA
NZ$242
27 Sept - 28 Sept
includes taxes & fees
Lakeside Inn
Motel 6 Danvers, MA - Boston North

Motel 6 Danvers, MA - Boston North

65 Newbury Street/US Route 1 North Danvers MA
NZ$256
28 Sept - 29 Sept
includes taxes & fees
Motel 6 Danvers, MA - Boston North
Best Western Adams Inn Quincy-Boston

Best Western Adams Inn Quincy-Boston

29 Hancock St Quincy MA
NZ$352
29 Sept - 30 Sept
includes taxes & fees
Best Western Adams Inn Quincy-Boston
Best Western Plus North Shore Hotel

Best Western Plus North Shore Hotel

50 Dayton St Danvers MA
NZ$432
27 Sept - 28 Sept
includes taxes & fees
Best Western Plus North Shore Hotel

Find out more about Winchester

Top reasons to visit Winchester

  • Charming Streets: Stroll through Winchester's picturesque streets, filled with friendly locals and inviting cafes.
  • Outdoor Activities: Enjoy urban parks and local swimming spots, perfect for family-friendly adventures.
  • Historic Attractions: Discover the rich history of Winchester through its vibrant neighbourhoods and historic sites.
  • Unique Accommodation: Stay in cozy boutique hotels or B&Bs, with options for all types of travellers.
  • Shopping and Entertainment: Explore local boutiques, shop at the mall, or catch a film at nearby cinemas.

Find great hotels near Winchester

Discover a range of inviting accommodation options in Winchester, Massachusetts, perfect for every type of traveller. Whether you're looking for a hotel or a cosy bed and breakfast, you'll find pet-friendly and LGBTQIA welcoming options that cater to business needs as well. Explore Winchester hotels and those nearby, ensuring a delightful stay close to local attractions, including the popular swimming spots.

  • citizenM Boston North Station: Located a mere 11.3km from Winchester, citizenM Boston North Station is a contemporary 4-star hotel aimed at business travellers. With a guest rating of 9.4 out of 10, this stylish lodging features modern, compact rooms equipped with smart technology, allowing guests to control lighting, temperature, and entertainment at their fingertips. The hotel boasts a vibrant communal space, perfect for networking and relaxation, along with a 24-hour canteen serving delicious meals and drinks. With its focus on comfort and convenience, citizenM is an ideal choice for those seeking a seamless business travel experience.
  • Hyatt Regency Boston/Cambridge: Just 11.3km from Winchester, the 4-star Hyatt Regency Boston/Cambridge holds a guest rating of 9.0 out of 10 and is well-regarded for its pet-friendly approach, making it a great option for travellers with furry companions. The hotel offers spacious rooms with picturesque views of the Charles River, along with amenities tailored for both business and leisure guests. With a variety of dining options and inviting common areas, guests can unwind or network. The pet policy ensures a welcoming atmosphere for those travelling with pets, further enhancing the comfort of your stay.
  • Four Points by Sheraton Boston Newton: This 3.5-star hotel, located 11.3km from Winchester, is well-rated at 8.4 out of 10 and is ideal for families, couples, and business travellers alike. Four Points by Sheraton Boston Newton features romantic packages and amenities designed for children, including breakfast options and video game consoles. Guests can enjoy spa services and an indoor pool, creating a relaxing atmosphere for families and couples. With its friendly service and family-oriented facilities, it offers a delightful balance of relaxation and enjoyment.

Where to stay in Winchester

Winchester, Massachusetts, offers a delightful blend of family-friendly activities and historical charm, making it an ideal weekend getaway. Explore its picturesque streets, where friendly locals enhance the urban atmosphere. Nearby, you’ll find vibrant neighbourhoods steeped in history, perfect for leisurely strolls. From outdoor parks to inviting cafes, Winchester is a charming destination that caters to all ages, providing a memorable experience that captures the essence of New England hospitality.

  • Boston: As a bustling metropolis, Boston is a vibrant city filled with history and culture. Situated within easy reach of Winchester, it attracts visitors year-round, with peak seasons in July, August, and October. Whether you're interested in education, music concerts, or shopping, Boston offers a variety of experiences for every traveller. Don't miss iconic landmarks such as historic sports stadiums and event venues, which reflect the city's rich sporting heritage. The blend of modern amenities and historical charm makes Boston a must-visit on your itinerary.
  • Woburn: Located a mere 3.2km from Winchester, Woburn is a charming city that appeals to families, business travellers, and those seeking a city-themed experience. Visitor numbers peak in April, July, and September, making it a great stop throughout the year. Woburn offers a selection of shopping centres and educational opportunities, with proximity to historic colleges. Enjoy the local attractions, including beautiful beaches and event venues, which provide a perfect backdrop for relaxation and exploration.
  • Cambridge: Just 9.7km from Winchester, Cambridge is renowned for its prestigious universities and a vibrant cultural scene. Visitor traffic remains steady throughout the year, with peaks in April, July, and September. Cambridge is ideal for families and those on business trips, providing access to shopping centres and educational institutions. Highlights include historic college campuses and sports stadiums, as well as numerous event venues that showcase the city's dynamic spirit. Explore the charming streets and soak in the academic atmosphere that defines Cambridge.

Things to do in Winchester

Shopping

In Winchester, you can find local boutiques like The Winchester Book and Gift Shop for unique souvenirs. If you're up for a drive, head to the nearby Woburn Mall for a variety of retail options, or check out the Burlington Mall for a larger shopping experience.

Recreation

Explore the serene atmosphere of the Winchester Wellness Centre, where you can indulge in rejuvenating spa treatments and holistic therapies. Afterward, enjoy a leisurely stroll through the picturesque Winchester Town Common, offering a tranquil setting for reflection and relaxation amidst nature.

Adventure

Explore the scenic trails at the Horn Pond Reservation for a refreshing hike surrounded by natural beauty. Engage in kayaking or canoeing on the pond for a thrilling experience while enjoying the serene environment. Don’t miss the chance to cycle along the local pathways for an exhilarating ride.

Nightlife

Winchester offers a quaint nightlife with cosy bars and eateries. Enjoy a craft beer at a local pub or relax with friends over dinner at a charming restaurant. The atmosphere is welcoming, making it an ideal spot for a laid-back evening out.

*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 on your trip to Winchester, consider visiting between December and February when accommodation prices are lower. Sundays are typically the cheapest days to stay, while Saturdays tend to be the priciest. Use Expedia to customise your travel preferences and filter for eco-certified hotels to find sustainable options. You can also save by booking a package deal that combines your hotel, flights, and activities. Lastly, take advantage of free local attractions and affordable public transport to get around while exploring this charming town.

  • 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 wizard to customise your travel preferences, such as your budget, preferred location, and the type of accommodation you desire. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some dollars by combining your Winchester hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Winchester

Winchester, Massachusetts, is perfect for outdoor family vacations and city-themed adventures. The area boasts popular attractions such as urban parks, historic sites, and vibrant streets, catering to those seeking culture and outdoor experiences. Visitors can also explore local swimming options, nearby resorts, and access to Winchester Hospital for added convenience. With its unique offerings, Winchester promises a memorable experience for tourists.

  • Fenway Park: As a historic sports stadium, Fenway Park offers a unique glimpse into America's baseball culture. With its iconic Green Monster and vibrant atmosphere, it’s a must-visit for sports enthusiasts. Located 12.9km from Winchester, you can immerse yourself in the excitement of a live game or take a guided tour to explore its rich history.
  • Boston Common: This urban park, also 12.9km away, is the oldest public park in the United States. With lush greenery and scenic walking paths, Boston Common is a delightful place for families and outdoor lovers to relax and enjoy a picnic amidst the city’s hustle and bustle.
  • Boston Marathon Finish Line: Situated on Boylston Street, this iconic location marks the end of the prestigious Boston Marathon. The area is vibrant with city energy, making it a fascinating spot to experience the spirit of endurance and community that surrounds this historic race, just 12.9km from Winchester.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Flying into Winchester, Massachusetts, is convenient with major airports nearby. BOSton Logan International Airport (BOS) is located 14.5km from Winchester and offers excellent hotels such as the 5-star Encore Boston Harbor and InterContinental Boston, both just a couple of miles away. Hartford Bradley International Airport (BDL) is 140.0km away, with nearby options like the 4-star DoubleTree by Hilton Hartford, just 1.6km from the airport. Providence T.F. Green Airport (PVD) is 85.3km from Winchester, with the Omni Providence Hotel and Graduate by Hilton Providence both located 11.3km from the airport. Each hotel offers easy access to their respective airports for a hassle-free journey.

Frequently asked questions

What is the best area to stay in Winchester?
The best area to stay in Winchester, Massachusetts, is right in the heart of Winchester Center, particularly near Main Street.Winchester Center is the town's main commercial and social hub. It's a compact and walkable area featuring a variety of local shops, cafes, and restaurants. The town common, a central green space, is a prominent landmark, often hosting community events. The area around Main Street and Thompson Street provides easy access to these amenities and the commuter rail station.For couples looking for a relaxed and upscale experience, Winchester Center is an excellent choice. You'll find charming independent boutiques for a leisurely browse and a selection of quality restaurants for evening meals. The proximity to the commuter rail also offers convenient day trips into Boston without the need for a car.Families will also find Winchester Center appealing due to its proximity to recreational facilities and open spaces. The town common is superb for children to play, and there are often family-friendly events happening.
When is the best time to go to Winchester?
The best time to go to Winchester, Massachusetts, is during the spring (late April to early June) and autumn (September to October) months. These seasons offer pleasant weather conditions for exploring the town and its surroundings.Spring in Winchester brings blooming flowers and trees, particularly noticeable around the Middlesex Fells Reservation, which offers walking trails and scenic views. Temperatures are mild, typically ranging from 10°C to 20°C, making it comfortable for outdoor activities like visiting the Wright-Locke Farm or enjoying a stroll along the Aberjona River. Couples often appreciate the picturesque scenery and the opportunity for relaxed outdoor experiences.Autumn is another excellent time, with the New England foliage displaying spectacular colours. The weather remains mild, with temperatures generally between 10°C and 18°C, great for enjoying the town's parks and conservation lands. Families might particularly enjoy apple picking at local farms or participating in seasonal events.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to 'My Trips' and selecting your reservation. To find flexible deals, filter your search by 'Fully refundable property' for hotels in Winchester.
How can I save on a hotel booking in Winchester with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Winchester hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Winchester?
Prices for hotels in Winchester often vary, but you can find a great deal from NZ$170 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by 'Price: low to high' for our cheapest rates.

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