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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Our top choices for Winchester hotels

A spacious lobby with a fireplace, bookshelves, and a checkered floor.
A modern interior with a bar area, seating, and a mural on the ceiling.
A modern hotel room with a large bed, a leather sofa, and a view of the city through large windows.
A modern lobby with a curved seating area, a large plant, and a mural on the wall.

1. The Revolution Hotel

The Revolution Hotel
South End
United States
Brenna
$268 nightly
$312 total
Oct 13 - Oct 14
Total with taxes and fees
The Revolution Hotel
The exterior of the Harborside Inn Boutique Hotel with a glass entrance, numbered room 185, and two large potted plants at the entrance.
An outdoor cafe with tables and chairs, a building entrance, and a street sign.
A modern lobby with leather seating, tables, and a large chandelier.
A spacious lounge area with a wooden floor, multiple seating options including sofas and ottomans, a television screen, and a ceiling with circular light fixtures.

2. Harborside Inn Of Boston

Harborside Inn Of Boston
Downtown Boston
United States
Priscilla
$449 nightly
$523 total
Oct 4 - Oct 5
Total with taxes and fees
Harborside Inn Of Boston
A restaurant with a long dining area, high ceilings, and exposed beams. Tables are set with glassware and centerpieces.
A couple walking on a sidewalk with a restaurant named "THE DAGNY" in the background.
A building with a sign reading "THE DAGNY" and a brick facade. There are two bicycles parked in front.
A grand lobby with a large arched entrance, a high ceiling with a detailed mural, and a view of the street outside.

3. The Dagny Boston

The Dagny Boston
Downtown Boston
United States
Danny
$450 nightly
$524 total
Oct 2 - Oct 3
Total with taxes and fees
The Dagny Boston
A woman seated in a chair reading a book in a room with a fireplace, wooden floor, and decorative wall panels.
A hotel room with a large window offering a city view, a television, a patterned armchair, a sofa, and a small table with a vase of flowers.
An indoor swimming pool with a skylight ceiling, seating area with cushions, and a 'No Diving' sign.
A waterfront cityscape with high-rise buildings, a bridge, and a river.

4. Seaport Hotel Boston

Seaport Hotel Boston
Seaport District
United States
Tom
$344 nightly
$399 total
Oct 4 - Oct 5
Total with taxes and fees
Seaport Hotel Boston
A restaurant with wooden flooring, multiple dining tables, and hanging chandeliers.
A bar area with a long counter, multiple bar stools, and a decorative mural on the wall.
A building facade with multiple windows and decorative arches.
A grand arched doorway with intricate moldings and a modern light fixture above.

5. The Godfrey Hotel Boston

The Godfrey Hotel Boston
Downtown Boston
United States
Julia
$419 nightly
$488 total
Oct 4 - Oct 5
Total with taxes and fees
The Godfrey Hotel Boston
A modern restaurant with round tables and chairs, large windows with a city view, and a geometric patterned floor.
A modern living room with a city view, featuring a sofa, armchairs, a coffee table, and a dining area.
A modern hotel lobby with a bar area, seating arrangements, and a fireplace.
A hotel room with a large bed, a desk, a chair, and a view of a cityscape through a large window.

6. Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
Seaport District
United States
Laila
$394 nightly
$459 total
Oct 2 - Oct 3
Total with taxes and fees
Omni Boston Hotel at the Seaport
A bar area with wooden stools, a bar counter, and a decorative ceiling.
A modern lobby with a fireplace, two armchairs, and a variety of decorative items on shelves.
A building with a large number '161' sign, Club Quarters flags, and a storefront with 'STLE PUB' signage.
A hotel room with a bed, a desk with a laptop and headphones, a chair, a bedside table with a lamp, and a large window with curtains.

7. Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
United States
Ashley
$382 nightly
$445 total
Oct 4 - Oct 5
Total with taxes and fees
Club Quarters Hotel Faneuil Hall, Boston
A modern bedroom with a large bed, a nightstand, a lamp, a potted plant, and a view of a cityscape at night.
A grand hotel with a prominent marquee, a large staircase, and well-maintained gardens.
A large hotel with a curved facade and the name "Encore" illuminated on the top.
A modern hotel room with a large window offering a city view, a flat-screen TV, a sofa, a coffee table, and a decorative painting.

8. Encore Boston Harbor

Encore Boston Harbor
Everett
United States
Vilene
$321 nightly
$359 total
Oct 18 - Oct 19
Total with taxes and fees
Encore Boston Harbor
A multi-story hotel with a distinctive stepped design, featuring illuminated signage and a reflection in the water.
An outdoor seating area with wooden tables and chairs, surrounded by greenery and illuminated by lanterns.
A modern hotel room with a large window offering a city view, a sofa, a teal armchair, a small table with a plant, a bed, and a TV.
A spacious hotel lobby with a modern design, featuring a large seating area, a staircase leading to an upper floor, and a view of the city skyline through large windows.

9. Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge
MIT
United States
Vanessa
$271 nightly
$315 total
Oct 4 - Oct 5
Total with taxes and fees
Hyatt Regency Boston/Cambridge
A room with a large window overlooking a historic building with a dome.
A modern kitchen area with a wooden table, chairs, and a variety of food items including apples and pastries. There are coffee makers and a coffee station with cups and a milk frother.
A hotel room with a desk, a chair, a TV, a lamp, and a minibar.
A modern building with a covered entrance, large windows, and a parking area.

10. The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta
Back Bay
United States
Anna
$254 nightly
$296 total
Oct 4 - Oct 5
Total with taxes and fees
The Midtown Hotel MOD Collection by Sonesta
The Omni Parker House hotel facade with a classic architectural design, featuring ornate detailing and a grand entrance.
A covered balcony with outdoor seating, a view of a cityscape, and a building with a dome in the background.
A luxurious lobby with ornate wood paneling, a grand chandelier, and elegant seating arrangements.
A hotel room with a large bed, a desk, a chair, a TV, and artwork on the wall.

11. Omni Parker House

Omni Parker House
Downtown Boston
United States
Elly
$504 nightly
$587 total
Oct 4 - Oct 5
Total with taxes and fees
Omni Parker House
A bar area with a city view, bar stools, and a bar counter.
A modern building with a curved facade, large windows, and a glass entrance.
An outdoor seating area with a green sofa, a blue chair, and red chairs.
A modern lobby with a blue sofa, colorful ottomans, and a large window with a city view.

12. citizenM Boston Back Bay

citizenM Boston Back Bay
Fenway–Kenmore
United States
Jingjing
$287 nightly
$334 total
Oct 4 - Oct 5
Total with taxes and fees
citizenM Boston Back Bay
A modern living room with a sofa, a coffee table, and a bookshelf filled with books and decorative items.
A modern interior with large windows, a red sofa, and a city view.
A modern building with a glass facade, a sign for TD Garden, and a North Station sign.
A rooftop terrace with a red bench, tables, chairs, and hanging lights.

13. citizenM Boston North Station

citizenM Boston North Station
West End
United States
Ivo John
$251 nightly
$292 total
Oct 4 - Oct 5
Total with taxes and fees
citizenM Boston North Station
A hotel room with a bed, a nightstand, a wall-mounted lamp, and a door leading to a bathroom.
The exterior of the Copley Square Hotel with its classic architecture and prominent signage.
A reception area with a black wall, wooden desk, and pendant lighting.
A checkered floor, a staircase with a handrail, a round mirror, and a small table with a globe.

14. Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel
Back Bay
United States
Anonymous traveler
$279 nightly
$325 total
Oct 4 - Oct 5
Total with taxes and fees
Copley Square Hotel, a FOUND Hotel
A spacious lobby with a large mural of a city skyline and a waterfront view.
A modern indoor space with seating areas, a central staircase, and a wooden ceiling.
A modern building with a restaurant named "O'Connors" on the ground floor.
A hotel with a modern facade, multiple floors, and a prominent entrance.

15. The Westin Boston Seaport District

The Westin Boston Seaport District
Seaport District
United States
luis a
$311 nightly
$362 total
Oct 18 - Oct 19
Total with taxes and fees
The Westin Boston Seaport District
A modern living room with a sectional sofa, a round coffee table, and a chandelier.
Two people dining at a restaurant with various dishes and drinks on the table.
A multi-story building with a prominent sign reading 'HYATT REGENCY' at the top.
A swimming pool with lanes, a sunroof, and exercise equipment in the background.

16. Hyatt Regency Boston

Hyatt Regency Boston
Downtown Boston
United States
Annette
$329 nightly
$383 total
Oct 4 - Oct 5
Total with taxes and fees
Hyatt Regency Boston
A multi-story hotel with a covered entrance and a snow-covered ground.
A breakfast buffet with a variety of fruits and a coffee station.
A reception area with a curved wooden desk, a computer, and a Christmas tree.
A hotel room with a large bed, a desk, a chair, and two bedside lamps.

17. La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville
Assembly Square
United States
Melissa
$214 nightly
$239 total
Oct 18 - Oct 19
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Boston Somerville
A modern lounge area with sofas, round tables, and a bar with multiple seating options.
A modern interior with a bar area, seating, and a unique black coffee table.
A modern living room with a sectional sofa, a round coffee table, and a floor lamp with lights.
A modern kitchen with a marble countertop, bar stools, and a flat-screen TV mounted on the wall.

18. Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea
Chelsea
United States
Ana
$266 nightly
$297 total
Oct 18 - Oct 19
Total with taxes and fees
Doubletree By Hilton Boston Logan Airport Chelsea
A modern hotel room with a geometric patterned floor, a brown leather sofa, a flat-screen TV mounted on the wall, and a small table with a lamp.
The exterior of the Arcadian Hotel with its illuminated signage.
A hotel room with two beds, a desk, a chair, a TV, and a large window.
A spacious lobby with a geometric patterned floor, a staircase, seating area, and a reception desk.

19. Arcadian Hotel

Arcadian Hotel
Coolidge Corner
United States
Janine Patrice
$253 nightly
$283 total
Oct 12 - Oct 13
Total with taxes and fees
Arcadian Hotel
An outdoor seating area with a fire pit, sofas, and chairs.
A modern lounge with large windows, a bar area, and seating arrangements.
A modern building with a flat roof and large windows, situated by a calm body of water with a chain barrier in the foreground.
A red building with a sign reading "Boston Tea Party - Ships & Museum" docked by a waterway with a tall ship and a smaller boat.

20. Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District
Seaport District
United States
Casey
$399 nightly
$465 total
Oct 4 - Oct 5
Total with taxes and fees
Hyatt Place Boston/Seaport District
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Where to stay in Winchester

Discover the charm of Winchester, Massachusetts, where family-friendly vibes meet urban energy. Stroll along Washington Street and Cummings Street for local shops and eateries, or explore the nearby historical sites just miles from Lexington, New Hampshire. Don't miss a visit to Winchester Hospital for community insights and culture.
A street lined with historic buildings, including the Union Oyster House and Yankee Publishing Building.
A historic building with "QUINCY MARKET" sign, surrounded by modern buildings and a clock tower.
A historic building with a clock tower in a cityscape.
A city skyline with numerous high-rise buildings and a marina filled with sailboats.
A waterfront promenade with a wooden boardwalk, a bridge, and a city skyline with modern buildings.

Boston

Discover Boston, a vibrant city perfect for travelers seeking a rich cultural experience. With attractions like the historic Fenway Park, the expansive Boston Common, and the bustling TD Garden, there's something for everyone to enjoy. Situated in Boston, Winchester offers easy access to these highlights, making it an ideal base for exploring the city. Choosing Boston for your stay ensures you're at the heart of it all, ready to immerse yourself in urban adventures and local charm.

A calm lake with a weeping willow, a bird, and a house in the background.
A red brick building with white columns and a green lawn with pink flowers.
A historic building with a red roof and intricate architecture.
A group of ducklings with a goose nearby on a gravel surface.
A brick building with a sign that reads "CITY HALL 10 COMMON STREET".

Woburn

Experience the charm of Woburn, a top-rated choice for travelers seeking a blend of city excitement and family-friendly activities. This vibrant city offers easy access to local attractions like the historic Harvard University and the bustling shopping mall center, as well as the beautiful Boston Common park. Located about 2 miles from Winchester, Woburn serves as a fantastic home base for those eager to explore the area's rich culture and recreational opportunities, making it an excellent hotel booking choice.

An aerial view of a town with a mix of residential and commercial buildings, a prominent green-roofed building, and a body of water in the distance.

West Medford

Make your vacation planning effortless by staying in West Medford, a haven for families, couples, and business travelers thanks to its vibrant mix of outdoor and city experiences. Explore nearby attractions like Fenway Park and Harvard University, or unwind at Boston Common, creating memorable moments during your visit. Located about 2 miles by car from Winchester, West Medford offers easy access to a blend of education and entertainment, making it a smart choice for your stay.

A vintage truck parked in a field with a wooden house in the background.
A red wooden house with white trim and a grey roof.
A river surrounded by trees and tall grasses.
Photo by Ana Lei
A cityscape with a mix of residential and commercial buildings, a bridge, and distant mountains under a cloudy sky.
Photo by Brittney Geary
A city skyline with industrial buildings and a highway.
Photo by Ana Lei

Medford

Medford stands out as a prime spot for travelers interested in city and culture experiences. With attractions like the historic Harvard University and the lively Fenway Park nearby, visitors can immerse themselves in rich history and vibrant activities. This city is easily accessible, located about 3 miles by car from Winchester, making it a smart choice for your stay. Whether you're here for a weekend getaway or a family trip, Medford offers a welcoming ambiance for all.

A round building with a dome, surrounded by a grassy area and trees, with houses in the background.
An aerial view of a city with two large lakes, a highway, and residential areas.
An aerial view of a residential area with autumn-colored trees and houses.
A cityscape with a river, green spaces, and various buildings.
A lake with ducks and geese on the shore.
Photo by Pablo Funes

Arlington

Travelers visiting the area often choose Arlington, especially families and weekend getaway seekers looking for a blend of city and culture. This charming city offers easy access to historic attractions like Harvard University and the vibrant shopping centers, making it ideal for those wanting to explore. Located about 3 miles by car from Winchester, Arlington’s convenient location allows for a seamless travel experience, making it a smart choice for your stay.

Stay near popular attractions in and around Winchester

Winchester, Massachusetts, offers a delightful blend of outdoor adventures, family-friendly activities, and rich history. Explore urban parks, historic sites, and renowned colleges nearby, making it an ideal base for culture seekers. Plus, check out near Winchester hospital reviews for convenient healthcare options during your stay.
A cityscape with a prominent stadium, a busy intersection, and a skyline with high-rise buildings.

Fenway Park

9.2/10 (11,009 reviews)
Experience the best of Boston's sports culture at Fenway Park, a historic stadium that captures the heart of baseball fans. Located about 9 miles by car from Winchester, it offers a vibrant atmosphere steeped in tradition. Staying near Fenway Park puts you right in the action of Boston's lively sports scene.
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A historic building with a clock tower, a large gate, and a well-maintained lawn.

Harvard University

9.2/10 (6,542 reviews)
Ideal for a quick visit and a memorable day out, Harvard University offers a unique blend of history and culture. Located about 6 miles from Winchester, this prestigious institution invites you to explore its beautiful campus and rich traditions. Staying nearby provides easy access to its vibrant atmosphere.
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A public park with a large fountain, surrounded by trees and modern buildings.

Boston Common

9.4/10 (18,299 reviews)
Ideal for travelers interested in vibrant city parks, Boston Common offers a perfect blend of outdoor space and historical significance. Located about 8 miles by car from Winchester, this urban park is an inviting spot for families to relax and enjoy the city’s lively atmosphere, making it a convenient stop during your visit.
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A modern building with 'GARDEN' signage, a waterfront, and a cable-stayed bridge.

TD Garden

9.2/10 (7,449 reviews)
No trip is complete without a visit to TD Garden, a premier venue for sports and entertainment enthusiasts. This vibrant arena hosts a variety of events, from thrilling hockey games to unforgettable concerts. Located about 7 miles by car from Winchester, staying near TD Garden offers easy access to Boston's lively atmosphere.
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A large building with a dome and columns, surrounded by well-maintained hedges and trees.

Massachusetts Institute of Technology

9.2/10 (1,465 reviews)
A standout venue known for its rich academic history and vibrant culture, the Massachusetts Institute of Technology offers visitors an inspiring glimpse into innovation and technology. Located about 8 miles by car from Winchester, this iconic institution is perfect for those looking to explore cutting-edge research and stunning architecture, making it a convenient stop during your visit.
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A modern sculpture in a park with autumn trees and a historic building in the background.

Boston University

8.8/10 (4,994 reviews)
For cultural explorers, Boston University offers a captivating blend of history and vibrant campus life. This historic university showcases diverse cultural vibes and stunning architecture. Located about 9 miles by car from Winchester, it provides easy access to enriching experiences and events, making it a convenient stop during your visit.
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A city skyline at sunset with sailboats on the water.

Tufts University

8.8/10 (122 reviews)
An iconic landmark that appeals to students and history buffs alike, Tufts University offers a vibrant campus with modern architecture and a lively atmosphere. Located about 3 miles from Winchester, it's an easy visit to experience its unique blend of academics and community. Staying nearby allows for convenient access to this cultural hub.
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A sidewalk lined with brick buildings, outdoor cafes, and pedestrians.

Newbury Street

9.2/10 (955 reviews)
A must-see for city explorers, Newbury Street offers vibrant shopping, dining, and art experiences amidst its charming brownstone buildings. Located about 9 miles by car from Winchester, it’s an easy destination for a lively day trip, making it a great base for your Boston adventures.
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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

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Everything was perfect except l lost some money at the casino"
Bryan 1-night trip
Posted less than an hour ago
Encore Boston Harbor
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

10/10 Excellent
"My husband and I loved our stay!!! Our room view was awesome every night and morning! You could also sit outside by the harbor and enjoy a walk with the stunning view! My husband called ahead for our anniversary and they did this beautiful presentation on the bed! The bed was comfortable, loved the bathroom lighting. The clam chowder was so lovely. The closeness to the airport was a plus with the shuttle and you didn’t hear any airplane noise inside. We used the shuttle for the train station as well and all of our shuttle drivers were a delight. A special shoutout to CHAD!!!! Chad is the man!! Hotel provided water as well."
Glory 3-night trip
Posted 3 hours ago
Hyatt Regency Boston Harbor
The Westin Boston Seaport District

The Westin Boston Seaport District

10/10 Excellent
"The only negative we have is not many TV channels to choose from, the food in your restaurants was very good, room was clean , pleasant smell, staff very friendly and helpful"
Mary Lou 3-night trip
Posted 4 hours ago
The Westin Boston Seaport District
The Dagny Boston

The Dagny Boston

10/10 Excellent
"Great stay and clean property. Location was perfect!"
Aaron 4-night trip
Posted 5 hours ago
The Dagny Boston
The Godfrey Hotel Boston

The Godfrey Hotel Boston

8/10 Good
"Rooms could be a little bigger and beds are on the soft side"
Joseph 3-night trip
Posted 6 hours ago
The Godfrey Hotel Boston
citizenM Boston North Station

citizenM Boston North Station

10/10 Excellent
"Through several delays and cancellations, we were forced to have an unexpected overnight stay in Boston. It was the best 24 hour StayCation ever! This hotel was so adorable! From the unique check-in experience to the huge soft beds to the delicious bar options that even to a fabulous breakfast. We totally enjoyed our stay! We will visit again and look for more locations in other states!"
James 1-night trip
Posted 7 hours ago
citizenM Boston North Station
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

10/10 Excellent
"VANESSA THE FRONT DESK WAS VERY GOOD!"
Jaime 1-night trip
Posted 9 hours ago
Hilton Garden Inn Tewksbury Andover
The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

10/10 Excellent
"."
Markisha 3-night trip
Posted 2 days ago
The Westin Copley Place, Boston, a Marriott Hotel

More cheap stays in Winchester

The Inn on Arsenal

The Inn on Arsenal

100 N Beacon St Watertown MA
$126 nightly
$141 total
Sep 28 - Sep 29
Total with taxes and fees
8/10 Very Good! (437 reviews)
The Inn on Arsenal
Motel 6 Danvers, MA - Boston North

Motel 6 Danvers, MA - Boston North

65 Newbury Street/US Route 1 North Danvers MA
$130 nightly
$145 total
Sep 27 - Sep 28
Total with taxes and fees
Motel 6 Danvers, MA - Boston North
Lakeside Inn

Lakeside Inn

595 North Ave Wakefield MA
$137 nightly
$153 total
Sep 27 - Sep 28
Total with taxes and fees
Lakeside Inn
Ramada by Wyndham Boston

Ramada by Wyndham Boston

800 Morrissey Blvd Boston MA
$156 nightly
$182 total
Oct 1 - Oct 2
Total with taxes and fees
6.8/10 (1,913 reviews)
Ramada by Wyndham Boston
Best Western Plus North Shore Hotel

Best Western Plus North Shore Hotel

50 Dayton St Danvers MA
$210 nightly
$235 total
Sep 30 - Oct 1
Total with taxes and fees
Best Western Plus North Shore Hotel
enVision Hotel Boston Everett

enVision Hotel Boston Everett

1834 Revere Beach Pkwy Everett MA
$230 nightly
$256 total
Oct 4 - Oct 5
Total with taxes and fees
enVision Hotel Boston Everett

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Activities: Enjoy a variety of outdoor adventures, including urban parks and beautiful local parks perfect for relaxation.
  • Family-Friendly Attractions: Visit the Dropzone Waterpark for fun-filled water activities suitable for all ages.
  • Rich History: Explore historic sites that reflect Winchester's unique heritage and charm.
  • Charming Neighborhoods: Experience friendly locals and vibrant streets that make the area inviting.
  • Convenient Accommodation: Choose from a range of hotels and cozy bed & breakfasts that cater to diverse needs.

Find great hotels near Winchester

Winchester, Massachusetts offers a variety of accommodation options, including hotels and charming bed & breakfast establishments. Whether you're traveling for business or leisure, you'll find pet-friendly, LGBTQIA-welcoming options that cater to your needs. Explore the best hotels in Winchester for a comfortable stay, with convenient amenities and a warm atmosphere that make your visit enjoyable.

  • citizenM Boston North Station: CitizenM Boston North Station is a contemporary 4-star hotel renowned for its innovative design and modern amenities, boasting an impressive guest rating of 9.4. Located a short drive from Winchester, this hotel is ideal for business travelers seeking a chic and efficient stay. With a 24-hour business center, smart rooms featuring mood lighting and large flat-screen TVs, and a vibrant lounge area, it creates a dynamic environment for work and relaxation. Guests appreciate the on-site restaurant serving international cuisine and the stylish bar, perfect for unwinding after a busy day.
  • Red Roof Inn PLUS+ Boston - Woburn/Burlington: Red Roof Inn PLUS+ Boston - Woburn/Burlington offers budget-friendly accommodations just 4 miles from Winchester, making it a perfect choice for families and pet owners. This welcoming hotel is designed with comfort in mind, featuring family-friendly amenities such as free cribs and a pet-friendly policy that allows dogs and cats. Guests enjoy spacious rooms equipped with modern conveniences and the convenience of nearby dining options. The relaxed atmosphere ensures a pleasant stay for both children and pets, making it a great value for travelers.
  • Hyatt Regency Boston/Cambridge: Hyatt Regency Boston/Cambridge is a distinguished 4-star hotel, receiving a commendable guest rating of 9.0. Situated approximately 7 miles from Winchester, it is an excellent choice for business travelers and pet-friendly getaways. The hotel features state-of-the-art meeting facilities, a well-equipped fitness center, and spacious rooms with stunning views of the Charles River. Guests can indulge in on-site dining options and take advantage of the pet-friendly amenities, ensuring a comfortable stay for both guests and their furry companions. The blend of luxury and convenience makes this hotel a standout choice.

Where to stay in Winchester

Winchester, Massachusetts, offers a delightful blend of outdoor adventures and family-friendly attractions. Explore its charming neighborhoods, where friendly locals and a rich history create a welcoming atmosphere. Just a short drive away, you'll find convenient access to wineries and beautiful parks. Whether you're staying near the university or enjoying the vibrant city life, Winchester is the perfect base for unforgettable experiences in the greater Boston area.

  • Boston: As a vibrant metropolis, Boston is a cultural hub that offers an array of experiences for every traveler. Located a short distance from Winchester, this historic city boasts a rich history, renowned educational institutions, and a lively arts scene. Visitors flock to Boston for its iconic landmarks, such as historic sports stadiums and event venues. The peak travel seasons are during the summer months and October, making it an ideal time to enjoy outdoor festivals, concerts, and shopping in bustling malls. Whether you're interested in exploring the Freedom Trail or indulging in world-class dining, Boston promises an unforgettable urban experience.
  • Woburn: Just 2 miles away from Winchester, Woburn is a charming city that combines small-town warmth with urban amenities. This city attracts travelers seeking a mix of family-friendly activities and business opportunities. Popular attractions include shopping centers and historic college campuses. With visitor numbers peaking in the spring and summer, Woburn is perfect for those looking to enjoy outdoor events or a leisurely day at the beach. Its proximity to major highways also makes it a convenient base for exploring nearby cities. Enjoy the local eateries and the friendly atmosphere that Woburn has to offer.
  • Medford: Located 3 miles from Winchester, Medford is a city rich in cultural and historical significance. Known for its modern college universities and historic buildings, it caters to travelers interested in education and culture. With peak visitation in early spring and summer, Medford offers plenty of shopping and relaxation options, including spas to unwind after a day of exploration. The city's combination of historical charm and contemporary conveniences makes it an ideal stop for families and business travelers alike. Don't miss the chance to enjoy Medford’s unique blend of past and present.

Things to do near Winchester

Winchester, Massachusetts, offers a variety of outdoor and family-friendly activities perfect for a city-themed vacation. Visitors can enjoy educational attractions and explore local shopping centers. Exciting options include the Dropzone Waterpark for water fun and Skydive Perris for thrilling skydiving adventures, making it an ideal destination for adventure seekers and families alike.

Shopping

In Winchester, visit local shops for unique gifts and souvenirs. If you're up for a drive, head to the Burlington Mall, about 10 miles away, featuring popular retailers and dining options. Also, check out the Woburn District Shopping Center for a variety of stores and local finds.

Recreation

Experience luxury at the Country Club of Billerica, where you can enjoy upscale amenities and serene surroundings. The Tewksbury Country Club offers a relaxing atmosphere with exquisite dining options, while the Andover Country Club invites you to unwind amidst beautiful landscapes and top-notch golf facilities.

Adventure

Explore the scenic trails at the Middlesex Fells Reservation, perfect for hiking and mountain biking. Check out the picturesque Horn Pond for kayaking and paddleboarding, offering a refreshing way to enjoy the outdoors. Don't miss the local parks for picnicking and leisurely walks amidst nature.

Nightlife

Winchester offers a cozy nightlife with local favorites like the Tavern in the Square for lively gatherings and delicious food. For a laid-back evening, check out the Winchester Pub, where you can enjoy craft beers and friendly conversation with locals.

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

Booking tips and Expedia advantages for 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: Utilize Expedia’s search tool to customize your preferences, such as your budget, desired location, and preferred hotel type. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package deal.

Find the best attractions near Winchester

Winchester, Massachusetts, offers a delightful blend of outdoor activities, family-friendly attractions, and urban charm. Visitors can explore urban parks, historic sites, and vibrant streets, making it an ideal destination for those seeking culture and outdoor experiences. Whether you're looking to unwind in nature or delve into the area's rich history, Winchester has something for everyone to enjoy.

  • Fenway Park: Experience the excitement of America's pastime at Fenway Park, a historic sports stadium located 8 miles from Winchester. Known for its iconic Green Monster and rich history, this venue offers a vibrant atmosphere filled with passionate fans and unforgettable moments.
  • Boston Common: Enjoy the beauty of Boston Common, an urban park just 8 miles away. This lush green space is perfect for families, featuring playgrounds, walking paths, and picnic areas, all surrounded by the hustle and bustle of the city.
  • Copley Square: Discover Copley Square, a modern square also located 8 miles from Winchester. This vibrant hub is known for its stunning architecture, lively atmosphere, and local events, making it an ideal spot to soak in the city's energy.

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

When planning your trip to Winchester, Massachusetts, you have several airport options. BOSton Logan International Airport (BOS) is the closest, situated 9 miles away, with nearby hotels like the 5-star Encore Boston Harbor, InterContinental Boston, and Boston Harbor Hotel, all within 3 miles and easily accessible. Hartford Bradley International Airport (BDL) is 87 miles away, offering hotel choices such as the 4-star DoubleTree by Hilton Hartford and Simsbury 1820 House, which are conveniently located. Lastly, Providence T.F. Green Airport (PVD) is 53 miles from Winchester, with accommodations like the Omni Providence Hotel and Hotel Providence, both 7 miles from the airport, making your travel seamless.

Frequently asked questions

When is the best time to go to Winchester?
The best time to visit Winchester, Massachusetts, is during the late spring (May to June) and early autumn (September to October) when the weather is most pleasant for outdoor activities and exploring the town.During May and June, Winchester experiences comfortable temperatures, typically ranging from the 60s to low 70s Fahrenheit. This period is ideal for enjoying the town's parks, such as the Middlesex Fells Reservation, and walking along the Aberjona River. The blooming foliage adds to the town's appeal, making it a nice time for couples to enjoy scenic strolls and outdoor dining.Early autumn, from September to October, offers cooler, crisp air and the famous New England fall foliage. Temperatures generally range from the 50s to 60s Fahrenheit. This season is great for exploring the Winchester Farmers Market, visiting local apple orchards, or taking picturesque drives through the surrounding areas.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 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 much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from $141 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 the cheapest rate.

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