Hotels in Winchester

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Hilton Boston/Woburn
Hilton Boston/Woburn
3.5 star property
Woburn
8.6 out of 10, Excellent, (1,224 reviews)
This quiet Hilton in Woburn offers a relaxing retreat with an indoor pool and Spanish cuisine at Matadora restaurant. Just 15 minutes from Harvard Square and Faneuil Hall, with free WiFi and parking near Burlington Mall.
The price is $114
$127 total
includes taxes & fees
Feb 20 - Feb 21
Hilton Boston/Woburn
Hampton Inn Boston Woburn
Hampton Inn Boston Woburn
2.5 star property
Woburn
9.2 out of 10, Wonderful, (1,386 reviews)
Wake up to a free breakfast at this Woburn hotel, just 15 minutes from Faneuil Hall and Harvard Square. Splash in the indoor pool, unwind at the bar, or hit the fitness center. Enjoy free WiFi and parking while exploring Burlington Mall nearby.
The price is $111
$124 total
includes taxes & fees
Feb 20 - Feb 21
Hampton Inn Boston Woburn
Hyatt Place Boston/Medford
Hyatt Place Boston/Medford
3.0 star property
Medford
8.4 out of 10, Very Good, (1,671 reviews)
Just a short drive from downtown Boston, this hotel offers a free shuttle to area attractions. Enjoy 24-hour coffee service, complimentary breakfast, and access to the round-the-clock fitness center. Harvard Square and TD Garden are minutes away.
The price is $110
$123 total
includes taxes & fees
Feb 22 - Feb 23
Hyatt Place Boston/Medford
Lakeside Inn
Lakeside Inn
2.0 star property
Wakefield
7.6 out of 10, Good, (2,330 reviews)
Escape to a peaceful setting on the lake with stunning sunsets. Just 15 minutes from Tufts University, this Wakefield retreat offers a seasonal pool, fitness center, and Waves restaurant. Comfortable beds and free breakfast add to the serene experience.
The price is $90
$101 total
includes taxes & fees
Feb 17 - Feb 18
Lakeside Inn
Porter Square Hotel
Porter Square Hotel
3.0 star property
North Cambridge
9.2 out of 10, Wonderful, (1,001 reviews)
Unwind at this boutique hotel just minutes from Harvard University. The on-site restaurant and bar provide convenient dining, while free WiFi keeps you connected. Porter Square Station sits mere steps away, making Boston's attractions easily accessible.
The price is $120
$139 total
includes taxes & fees
Feb 28 - Mar 1
Porter Square Hotel
citizenM Boston Back Bay
citizenM Boston Back Bay
4.0 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (2,318 reviews)
Embrace urban charm at this modern Boston hotel near Newbury Street and Fenway Park. Enjoy international cuisine at canteenM after exploring Copley Square or working out in the 24-hour fitness center. Perfect transit access with two stations nearby.
The price is $101
$118 total
includes taxes & fees
Feb 22 - Feb 23
citizenM Boston Back Bay
Holiday Inn Express Boston - Saugus by IHG
Holiday Inn Express Boston - Saugus by IHG
3.0 star property
Saugus
8.6 out of 10, Excellent, (1,065 reviews)
Discover a peaceful retreat near Boston with a seasonal pool and 24-hour fitness center. Just 15 minutes from TD Garden and Faneuil Hall Marketplace, this hotel offers free breakfast, WiFi, and parking. Nearby shopping and dining at MarketStreet Lynnfield add to the convenience.
The price is $91
$102 total
includes taxes & fees
Feb 19 - Feb 20
Holiday Inn Express Boston - Saugus by IHG
Archer Hotel Boston/Burlington
Archer Hotel Boston/Burlington
4.0 star property
Burlington
9.8 out of 10, Exceptional, (1,002 reviews)
Experience contemporary design at this Burlington retreat, just minutes from Tufts University. Dive into the indoor pool, savor American cuisine at AKB, or energize in the 24-hour fitness center. With free WiFi and parking, plus Burlington Mall nearby, guests praise the attentive staff and pristine rooms.
The price is $135
$151 total
includes taxes & fees
Mar 6 - Mar 7
Archer Hotel Boston/Burlington
Hotel 1868
Hotel 1868
3.5 star property
Agassiz
9.6 out of 10, Exceptional, (1,001 reviews)
Immerse in Cambridge's historic charm at this hotel steps from Porter Square Station. The 24-hour fitness center keeps routines intact while the café offers quick bites. Harvard Square and Fenway Park await nearby for cultural exploration.
The price is $127
$147 total
includes taxes & fees
Feb 22 - Feb 23
Hotel 1868
La Quinta Inn & Suites by Wyndham Boston Somerville
La Quinta Inn & Suites by Wyndham Boston Somerville
3.0 star property
Assembly Square
7.6 out of 10, Good, (3,199 reviews)
Tucked near Assembly Station, this Somerville hotel offers free airport shuttles and daily continental breakfast. Explore Harvard Square and New England Aquarium with ease, then return to comfortable beds praised by travelers. The fitness center adds extra convenience.
The price is $80
$89 total
includes taxes & fees
Feb 22 - Feb 23
La Quinta Inn & Suites by Wyndham Boston Somerville
The Whitney Hotel
The Whitney Hotel
4.0 star property
Beacon Hill
9.6 out of 10, Exceptional, (514 reviews)
This charming Boston hotel offers a sophisticated retreat steps from Charles-MGH Station. Work out anytime in the 24-hour fitness center, borrow complimentary bikes to explore nearby attractions, or relax in the garden before dining at the on-site restaurant.
The price is $279
$325 total
includes taxes & fees
Feb 16 - Feb 17
The Whitney Hotel
Courtyard by Marriott Boston Downtown/North Station
Courtyard by Marriott Boston Downtown/North Station
3.0 star property
West End
9.4 out of 10, Exceptional, (1,246 reviews)
Wake up to city energy at this downtown Boston hotel steps from TD Garden. The Bistro offers breakfast and dinner, while the bar provides evening refreshment. North Station and Boston Harbor are minutes away for easy exploration of historic landmarks.
The price is $135
$157 total
includes taxes & fees
Feb 20 - Feb 21
Courtyard by Marriott Boston Downtown/North Station
Battery Wharf Hotel, Boston Waterfront
Battery Wharf Hotel, Boston Waterfront
4.5 star property
North End
8.8 out of 10, Excellent, (1,769 reviews)
Unwind at this waterfront Boston hotel with spa treatments and American cuisine at Cafe Amalfi. Just an 11-minute walk to New England Aquarium and Haymarket Station, plus 15 minutes to TD Garden. Enjoy free WiFi, a 24-hour fitness center, and sauna.
The price is $127
$175 total
includes taxes & fees
Feb 22 - Feb 23
Battery Wharf Hotel, Boston Waterfront
Hotel Indigo Boston Garden by IHG
Hotel Indigo Boston Garden by IHG
4.0 star property
West End
9.0 out of 10, Wonderful, (1,001 reviews)
Enjoy the perfect Boston location within a 15-minute walk to TD Garden and Quincy Market. Grab breakfast or dinner at Blake's Kitchen + Bar, unwind in the bar/lounge, or work out in the fitness center. North Station is just 3 minutes away on foot.
The price is $128
$149 total
includes taxes & fees
Feb 18 - Feb 19
Hotel Indigo Boston Garden by IHG
enVision Hotel Boston Everett
enVision Hotel Boston Everett
2.0 star property
Everett
8.6 out of 10, Excellent, (1,004 reviews)
The price is $84
$94 total
includes taxes & fees
Feb 16 - Feb 17
enVision Hotel Boston Everett
citizenM Boston North Station
citizenM Boston North Station
4.0 star property
West End
9.4 out of 10, Exceptional, (4,349 reviews)
Urban comfort awaits at this North Station hotel, just a 2-minute walk from TD Garden. The 24-hour fitness center and international restaurant complement stylish rooms with comfortable beds. Haymarket and Science Park stations provide easy city exploration.
The price is $110
$128 total
includes taxes & fees
Feb 22 - Feb 23
citizenM Boston North Station
Eurostars The Boxer
Eurostars The Boxer
4.0 star property
West End
8.6 out of 10, Excellent, (1,366 reviews)
Immerse yourself in Boston charm at this boutique hotel near Bowdoin and Haymarket stations. Enjoy American cuisine at Bulfinch Social, stay fit in the 24-hour gym, and explore nearby Quincy Market with help from the praised staff.
The price is $130
$171 total
includes taxes & fees
Feb 22 - Feb 23
Eurostars The Boxer
The Midtown Hotel MOD Collection by Sonesta
The Midtown Hotel MOD Collection by Sonesta
2.0 star property
Back Bay
7.6 out of 10, Good, (1,010 reviews)
Symphony Station is just a 2-minute walk from this centrally located Boston hotel. Explore nearby Copley Place and Newbury Street, both within a 10-minute stroll. After sightseeing, enjoy the convenience of free WiFi and nearby kayaking opportunities.
The price is $107
$125 total
includes taxes & fees
Feb 22 - Feb 23
The Midtown Hotel MOD Collection by Sonesta
Pennyweight Hotel Boston, Curio Collection by Hilton
Pennyweight Hotel Boston, Curio Collection by Hilton
4.0 star property
West End
8.2 out of 10, Very Good, (1,099 reviews)
Discover a tranquil atmosphere at this boutique Boston hotel, just steps from Haymarket Station and North Station. Guests praise the peaceful environment, convenient location for sightseeing, and attentive staff. Enjoy breakfast at 155 on Portland and access the 24-hour fitness center.
The price is $109
$162 total
includes taxes & fees
Feb 22 - Feb 23
Pennyweight Hotel Boston, Curio Collection by Hilton
The Verb Hotel
The Verb Hotel
3.5 star property
Fenway–Kenmore
9.6 out of 10, Exceptional, (2,002 reviews)
Immerse in this music-themed hotel with an outdoor pool and Japanese dining at Hojoko. Just minutes from Fenway Park, Boston attractions, and Kenmore Station, enjoy quiet rooms after exploring nearby restaurants and shops.
The price is $99
$162 total
includes taxes & fees
Feb 16 - Feb 17
The Verb Hotel
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.

Top landmarks in Winchester

Learn more about Winchester

Winchester is well-known for its attractions such as Winter Pond and Middlesex Fells Reservation.

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

Check out reviews of Winchester hotels guests love

Frequently asked questions

What accommodations do travelers like in Winchester?
Can I book a refundable hotel in Winchester?
If you want the flexibility to change your plans to Winchester, most accommodations offer refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
What will the weather in Winchester be like during my trip?
The warmest months in Winchester are usually July and August with an average temp of 69°F. January and February are the chilliest months when the average temp is 33°F. The rainiest months are December and October.
Why should I book my Winchester hotel through Hotels.com?
There are plenty of reasons to book your Winchester travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.