Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.

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Check prices for these dates

Next weekend
Jun 19 - Jun 21
In two weeks
Jun 26 - Jun 28

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Our top choices for Winchester hotels

Dinner served

Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport
3.0 star property
Revere
8.2 out of 10, Very Good, (5,641 reviews)
"Amazing breakfast, kind staff and very clean rooms!"
United States
Breanna
The price is ￥22,946
￥25,631 total
includes taxes & fees
Jul 6 - Jul 7
Hampton Inn Boston - Logan Airport
Lobby

Hilton Boston Logan Airport

Hilton Boston Logan Airport
4.0 star property
East Boston
9.0 out of 10, Wonderful, (3,838 reviews)
"Great place to stay "
United States
William
The price is ￥38,182
￥44,462 total
includes taxes & fees
Jul 2 - Jul 3
Hilton Boston Logan Airport
Exterior

Hilton Garden Inn Boston Logan Airport

Hilton Garden Inn Boston Logan Airport
3.0 star property
East Boston
9.2 out of 10, Wonderful, (2,305 reviews)
"Great stay!"
United States
Rachel
The price is ￥26,148
￥30,450 total
includes taxes & fees
Jul 6 - Jul 7
Hilton Garden Inn Boston Logan Airport
Lobby

Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport
2.5 star property
Revere
9.0 out of 10, Wonderful, (2,333 reviews)
"The cleanliness was awesome, breakfast was great and staff were top notch..."
United States
Frank
The price is ￥28,324
￥32,598 total
includes taxes & fees
Jul 6 - Jul 7
Comfort Inn & Suites Logan International Airport
Bar (on property)

Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District
3.0 star property
Seaport District
9.4 out of 10, Exceptional, (2,410 reviews)
"Great location, great staff and CLEAN ROOMS! Loved our stay"
United States
Gary
The price is ￥33,490
￥38,999 total
includes taxes & fees
Jul 5 - Jul 6
Hyatt Place 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, (2,889 reviews)
"Great for just an overnight.. clean room and friendly staff."
United States
Barbara
The price is ￥30,003
￥34,938 total
includes taxes & fees
Jul 6 - Jul 7
Hampton by Hilton at the Boston Seaport District
Exterior

Seaport Hotel Boston

Seaport Hotel Boston
4.0 star property
Seaport District
9.6 out of 10, Exceptional, (4,456 reviews)
"Great location, good price, clean and comfortable rooms."
United States
Amy
The price is ￥30,293
￥40,743 total
includes taxes & fees
Jul 5 - Jul 6
Seaport 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, (4,728 reviews)
"Great stay."
United States
Cassendra
The price is ￥30,638
￥42,210 total
includes taxes & fees
Jul 2 - Jul 3
Omni Boston Hotel at the Seaport
Front of property

Harborside Inn Of Boston

Harborside Inn Of Boston
4.0 star property
Downtown Boston
9.2 out of 10, Wonderful, (6,693 reviews)
"Love this spot close to everything will stay there again for a quick boston getaway"
United States
Carlos
The price is ￥35,910
￥41,817 total
includes taxes & fees
Jun 30 - Jul 1
Harborside Inn Of Boston
Lobby

The Westin Boston Seaport District

The Westin Boston Seaport District
4.0 star property
Seaport District
9.2 out of 10, Wonderful, (2,384 reviews)
"Great hotel!"
United States
Patricia
The price is ￥46,005
￥61,038 total
includes taxes & fees
Jun 20 - Jun 21
The Westin Boston Seaport District
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, (463 reviews)
"Excellent location for a short visit to Boston."
United States
Carlos
The price is ￥33,170
￥38,627 total
includes taxes & fees
Jul 12 - Jul 13
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, (1,464 reviews)
"Nice hotel within walking distance of attractions."
United States
Angela
The price is ￥26,440
￥35,453 total
includes taxes & fees
Jul 2 - Jul 3
Aloft by Marriott Boston Seaport District
Sports facility

Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor
4.0 star property
East Boston
9.2 out of 10, Wonderful, (1,906 reviews)
"It's a great place to stay"
United States
James
The price is ￥34,834
￥44,571 total
includes taxes & fees
Jul 5 - Jul 6
Hyatt Regency Boston Harbor
Breakfast, lunch, dinner and brunch served

The Dagny Boston

The Dagny Boston
4.0 star property
Downtown Boston
9.6 out of 10, Exceptional, (7,314 reviews)
"Good location and very comfortable hotel."
Canada
Gregory
The price is ￥36,522
￥48,126 total
includes taxes & fees
Jun 30 - Jul 1
The Dagny Boston
Reception

Hampton Inn & Suites Boston Crosstown Center

Hampton Inn & Suites Boston Crosstown Center
3.0 star property
South End
8.0 out of 10, Very Good, (1,685 reviews)
"Not far from the airport, clean and spacious room, decent breakfast, it works out well for my trip."
United States
Shaowen
The price is ￥23,520
￥27,389 total
includes taxes & fees
Jul 1 - Jul 2
Hampton Inn & Suites Boston Crosstown Center
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, (1,880 reviews)
"Very central and safe location and staff was great"
United States
earle
The price is ￥34,571
￥43,074 total
includes taxes & fees
Jun 21 - Jun 22
Battery Wharf Hotel, Boston Waterfront
Courtyard

DoubleTree by Hilton Boston - Downtown

DoubleTree by Hilton Boston - Downtown
4.0 star property
Bay Village
8.8 out of 10, Excellent, (1,021 reviews)
"great place to stay with great food!"
United States
Phoebe
The price is ￥31,431
￥36,602 total
includes taxes & fees
Jul 2 - Jul 3
DoubleTree by Hilton Boston - Downtown
Terrace/patio

Revere Hotel Boston Common

Revere Hotel Boston Common
4.0 star property
Bay Village
9.0 out of 10, Wonderful, (2,046 reviews)
"Super friendly staff, great location, and very nice, quiet rooms."
United States
Amy
The price is ￥36,639
￥50,130 total
includes taxes & fees
Jul 5 - Jul 6
Revere Hotel Boston Common
Restaurant

Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea
2.5 star property
Chelsea
9.0 out of 10, Wonderful, (3,014 reviews)
"Had a great stay!"
United States
Sara
The price is ￥26,017
￥29,061 total
includes taxes & fees
Jul 12 - Jul 13
Hampton Inn Boston Logan Airport Chelsea
In-room safe, blackout drapes, iron/ironing board, free WiFi

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel
4.0 star property
Back Bay
8.6 out of 10, Excellent, (4,041 reviews)
"Good staff and nice location"
United States
Francis
The price is ￥24,370
￥28,380 total
includes taxes & fees
Jul 6 - Jul 7
Copley Square Hotel, a FOUND 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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Stay near popular Winchester attractions

Winter Pond

4.5/5 (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.
See properties

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

Top Winchester Hotel Reviews

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"The hotel was fantastic."
Wilson 2-night trip
Posted less than an hour ago
Omni Boston Hotel at the Seaport

More cheap stays in Winchester

The Northshore Hotel - Boston/Danvers

The Northshore Hotel - Boston/Danvers

219 Newbury St. Danvers MA
The price is ￥17,466 per night from Jun 15 to Jun 16
￥17,466
￥19,509 total
Jun 15 - Jun 16
includes taxes & fees
7.6/10 Good! (1,033 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
Located 8.7 mi (14 km) from the heart of Winchester, Omni Boston Hotel at the Seaport is a top choice for your stay based on our traveler data. Other good options for your trip to the area are The Revolution Hotel and Seaport Hotel Boston. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals that Winchester has to offer?
Cozy 3BD 1BA near Beach T-10 Min from Boston: This vacation home rental outside of Winchester is equipped with a patio, free WiFi, and a Smart TV to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! You'll find that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
To access more information about picking new dates or cancelling your trip to Winchester, head over to our customer service page.
What are some accommodations with pools in Winchester?
Omni Boston Hotel at the Seaport: Hotel, 2-minute walk from Boston Convention and Exhibition Center. Features 4 restaurants, an outdoor pool, and a full-service spa. Seaport Hotel Boston and Hilton Boston Logan Airport are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What's the best hotel for staying near Logan International Airport (BOS)?
Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.
What is staying in Winchester like?
Visitors can enjoy all that Winchester has to offer including the soccer matches and lake views. Fenway Park, Encore Boston Harbor, and Harvard Square are some of the top sights around the area. In Winchester, there are 5 hotels and other accommodations to choose from. Find out more about Winchester.
What are the top places to visit in Winchester?
A couple of favorite places to visit are Winter Pond and Middlesex Fells Reservation. Additionally, you'll find Fenway Park and Encore Boston Harbor in the area. Check out what more to see and do in Expedia's Winchester guide.
How should I get around Winchester?
To see more of 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 temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.

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