Hotels in Winchester

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This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Where to stay in Winchester?

Free daily buffet breakfast

Best Western Plus New Englander

Best Western Plus New Englander
2.5 star property
Woburn
8.6 out of 10, Excellent, (1,094 reviews)
Serene sanctuary in Woburn with an indoor pool where tranquility meets convenience. Just a short drive from Harvard Square and MarketStreet Lynnfield, this hotel offers complimentary breakfast, WiFi, and parking with helpful staff ready to assist.
The price is $127
$141 total
includes taxes & fees
Aug 10 - Aug 11
Best Western Plus New Englander
Property amenity

Crowne Plaza Boston - Woburn by IHG

Crowne Plaza Boston - Woburn by IHG
4.0 star property
Woburn
8.6 out of 10, Excellent, (1,034 reviews)
Escape to this Woburn hotel with a refreshing indoor pool and welcoming bar. Just 15 minutes from Tufts University and near Burlington Mall, enjoy free WiFi, parking, and fitness center. Guests love the quiet atmosphere, helpful staff, and clean rooms.
The price is $103
$115 total
includes taxes & fees
Aug 17 - Aug 18
Crowne Plaza Boston - Woburn by IHG
Exterior

Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.2 out of 10, Wonderful, (1,472 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 $137
$153 total
includes taxes & fees
Aug 14 - Aug 15
Hampton Inn Boston Woburn
Breakfast, lunch, dinner and brunch served

The Dagny Boston

The Dagny Boston
4.0 star property
Downtown Boston
9.6 out of 10, Exceptional, (7,407 reviews)
Wake up to stunning views at this downtown Boston hotel, where comfortable beds await after a day of exploration. Just 10 minutes from Boston Harbor and the New England Aquarium, enjoy American cuisine at Fin Point or borrow free bikes to discover historical sites nearby.
The price is $181
$245 total
includes taxes & fees
Aug 27 - Aug 28
The Dagny Boston
Lobby

citizenM Boston North Station

citizenM Boston North Station
4.0 star property
West End
9.2 out of 10, Wonderful, (4,749 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 $170
$198 total
includes taxes & fees
Aug 9 - Aug 10
citizenM Boston North Station
Exterior

Seaport Hotel Boston

Seaport Hotel Boston
4.0 star property
Seaport District
9.6 out of 10, Exceptional, (4,651 reviews)
Indulge in waterfront tranquility at this Boston hotel with an indoor pool and American dining at TAMO Restaurant. Just 15 minutes from the Convention Center and near New England Aquarium, enjoy comfortable beds and helpful staff in a shopper-friendly location.
The price is $189
$254 total
includes taxes & fees
Aug 9 - Aug 10
Seaport Hotel Boston
Front of property

Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
8.2 out of 10, Very Good, (646 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 $98
$109 total
includes taxes & fees
Aug 2 - Aug 3
Lakeside Inn
Front of property

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront
4.5 star property
North End
8.8 out of 10, Excellent, (1,920 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 $259
$315 total
includes taxes & fees
Aug 2 - Aug 3
Battery Wharf Hotel, Boston Waterfront
View from property

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta
3.0 star property
Back Bay
8.2 out of 10, Very Good, (700 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 $166
$193 total
includes taxes & fees
Aug 9 - Aug 10
The Midtown Hotel MOD Collection by Sonesta
Lobby

Aloft by Marriott Boston Seaport District

Aloft by Marriott Boston Seaport District
3.0 star property
Seaport District
8.8 out of 10, Excellent, (1,481 reviews)
Wake up to harbor vibes at this Seaport District haven near the Convention Center and New England Aquarium. The indoor pool offers year-round relaxation while the on-site bar and café fuel your urban adventures. Just minutes from Broadway Station and South Station.
The price is $156
$211 total
includes taxes & fees
Aug 9 - Aug 10
Aloft by Marriott Boston Seaport District
Premium bedding, in-room safe, desk, laptop workspace

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, (1,430 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 $220
$256 total
includes taxes & fees
Aug 16 - Aug 17
Courtyard by Marriott Boston Downtown/North Station
Lobby

Homewood Suites by Hilton Boston Seaport District

Homewood Suites by Hilton Boston Seaport District
3.0 star property
Seaport District
9.2 out of 10, Wonderful, (1,529 reviews)
Explore Boston's waterfront district from this ideally located spot near Flynn Cruiseport and the Convention Center. Jump into the indoor pool, grab snacks at the deli, or relax in spacious rooms with sofa beds and refrigerators.
The price is $161
$185 total
includes taxes & fees
Aug 9 - Aug 10
Homewood Suites by Hilton Boston Seaport District
Exterior

Hampton by Hilton at the Boston Seaport District

Hampton by Hilton at the Boston Seaport District
3.0 star property
Seaport District
9.2 out of 10, Wonderful, (2,869 reviews)
Enjoy the convenience of an indoor pool, 24-hour fitness center, and free breakfast near Boston's Convention Center. Just a short drive from New England Aquarium and Boston Common, this Seaport District hotel offers easy access to Logan Airport and local transit stops.
The price is $155
$180 total
includes taxes & fees
Aug 9 - Aug 10
Hampton by Hilton at the Boston Seaport District
Front of property

Eurostars The Boxer

Eurostars The Boxer
4.0 star property
West End
8.8 out of 10, Excellent, (1,537 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 $168
$216 total
includes taxes & fees
Aug 23 - Aug 24
Eurostars The Boxer
Lobby

Hilton Boston Park Plaza

Hilton Boston Park Plaza
4.0 star property
Bay Village
8.4 out of 10, Very Good, (3,095 reviews)
Immerse yourself in Boston's charm at this elegant hotel near Arlington Station. Just steps from Boston Common and Copley Square, enjoy 2 restaurants, a fitness center, and an in-house Starbucks. Travelers rave about the central location and historic lobby.
The price is $171
$240 total
includes taxes & fees
Aug 9 - Aug 10
Hilton Boston Park Plaza
Exterior

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, (1,176 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 $114
$127 total
includes taxes & fees
Aug 2 - Aug 3
Holiday Inn Express Boston - Saugus by IHG
Lobby

Renaissance® Boston Seaport District

Renaissance® Boston Seaport District
4.0 star property
Seaport District
9.0 out of 10, Wonderful, (1,010 reviews)
Soak in Boston's energy at this harbor hotel with an indoor pool and sauna for post-sightseeing relaxation. The café serves breakfast while the bar mixes evening cocktails. Walk to South Station and reach New England Aquarium easily.
The price is $203
$277 total
includes taxes & fees
Aug 27 - Aug 28
Renaissance® Boston Seaport District
Exterior

The Bostonian Hotel Boston

The Bostonian Hotel Boston
4.0 star property
Government Center
8.2 out of 10, Very Good, (1,945 reviews)
Just steps from Quincy Market, this boutique hotel combines historic charm with modern convenience. Enjoy the health club, garden terrace, and on-site dining options. State St. Station is 4 minutes away for exploring Boston Harbor and nearby attractions.
The price is $207
$276 total
includes taxes & fees
Aug 23 - Aug 24
The Bostonian Hotel Boston
4 restaurants; breakfast, lunch, and dinner served

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4,862 reviews)
Immerse yourself in Boston's vibrant Seaport District at this upscale retreat with 4 restaurants and full-service spa. The outdoor pool offers refreshing breaks between walks to Flynn Cruiseport or the Convention Center, just 15 minutes away.
The price is $239
$319 total
includes taxes & fees
Aug 6 - Aug 7
Omni Boston Hotel at the Seaport
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers

The Verb Hotel

The Verb Hotel
3.5 star property
Fenway–Kenmore
9.6 out of 10, Exceptional, (2,095 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 $199
$278 total
includes taxes & fees
Aug 16 - Aug 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.
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Top landmarks in Winchester

Winter Pond

9.0/10 (2 reviews)
Winter Pond is 0.8 mi (1.3 km) from central Winchester, why not stop by during your stay. Our travelers also like the art galleries in the area— your cultural tour starts here. If you have fun at Winter Pond, you'll love Burlington Ice Palace and Griffin Photography Museum, both located nearby.
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Learn more about Winchester

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

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

Check out reviews of Winchester hotels guests love

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

8/10 Good
"Great place for families."
Trudy 2-night trip
Posted less than an hour ago
Hyatt Regency Boston/Cambridge

Frequently asked questions

What accommodations do travelers like in Winchester?
Guests like Seaport Hotel Boston, The Revolution Hotel and Omni Boston Hotel at the Seaport.
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.