Hotels in Winchester

Q: What accommodations do travelers like in Winchester?

Guests like Harborside Inn Of Boston , Hilton Boston Back Bay and Omni Boston Hotel at the Seaport .

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Dates

January 2026

February 2026

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Where to stay in Winchester?

Best Western Plus New Englander

Woburn

CNY689 total

includes taxes & fees

Jan 15 - Jan 16

Hyatt Place Boston/Medford

Medford

CNY857 total

includes taxes & fees

Jan 17 - Jan 18

La Quinta Inn & Suites by Wyndham Boston Somerville

Assembly Square

CNY530 total

includes taxes & fees

Feb 1 - Feb 2

Desk, laptop workspace, blackout drapes, iron/ironing board

Sonesta Simply Suites Boston Burlington

Burlington

CNY740 total

includes taxes & fees

Jan 17 - Jan 18

Hilton Boston/Woburn

Woburn

CNY888 total

includes taxes & fees

Jan 18 - Jan 19

Porter Square Hotel

North Cambridge

CNY799 total

includes taxes & fees

Jan 18 - Jan 19

Lakeside Inn

Wakefield

enVision Hotel Boston Everett

Everett

CNY769 total

includes taxes & fees

Jan 12 - Jan 13

citizenM Boston Back Bay

Fenway–Kenmore

CNY870 total

includes taxes & fees

Jan 15 - Jan 16

Cambria Hotel Boston Somerville

Spring Hill

CNY992 total

includes taxes & fees

Feb 1 - Feb 2

Hotel 1868

Agassiz

CNY799 total

includes taxes & fees

Jan 18 - Jan 19

Eurostars The Boxer

West End

CNY1,115 total

includes taxes & fees

Feb 9 - Feb 10

Holiday Inn Express Boston - Saugus by IHG

Saugus

CNY709 total

includes taxes & fees

Jan 15 - Jan 16

Hilton Boston Park Plaza

Bay Village

CNY1,010 total

includes taxes & fees

Feb 1 - Feb 2

Battery Wharf Hotel, Boston Waterfront

North End

CNY1,298 total

includes taxes & fees

Feb 1 - Feb 2

In-room safe, blackout drapes, iron/ironing board, free WiFi

Copley Square Hotel, a FOUND Hotel

Back Bay

CNY648 total

includes taxes & fees

Jan 25 - Jan 26

Wyndham Boston Beacon Hill

West End

CNY1,029 total

includes taxes & fees

Feb 1 - Feb 2

Doubletree By Hilton Boston Logan Airport Chelsea

Chelsea

CNY825 total

includes taxes & fees

Jan 13 - Jan 14

citizenM Boston North Station

West End

CNY943 total

includes taxes & fees

Jan 18 - Jan 19

Studio Allston Hotel

Brighton

CNY1,045 total

includes taxes & fees

Jan 13 - Jan 14

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Budget hotels in Winchester and vicinity

Standard Room, 1 Queen Bed | Premium bedding, in-room safe, iron/ironing board, free WiFi

Found Hotel Boston Common

Bay Village

CNY584 total

includes taxes & fees

Jan 18 - Jan 19

La Quinta Inn & Suites by Wyndham Boston Somerville

Assembly Square

CNY530 total

includes taxes & fees

Feb 1 - Feb 2

Copley Square Hotel, a FOUND Hotel

Back Bay

CNY648 total

includes taxes & fees

Jan 25 - Jan 26

Staypineapple, A Delightful Hotel, South End

South End

CNY674 total

includes taxes & fees

Jan 25 - Jan 26

Holiday Inn Express Boston - Waltham by IHG

Piety Corner

CNY725 total

includes taxes & fees

Jan 16 - Jan 17

Holiday Inn Express Boston - Saugus by IHG

Saugus

CNY709 total

includes taxes & fees

Jan 15 - Jan 16

Hampton Inn & Suites Boston Crosstown Center

South End

CNY726 total

includes taxes & fees

Jan 17 - Jan 18

Holiday Inn Express Chelmsford by IHG

Chelmsford

CNY772 total

includes taxes & fees

Jan 23 - Jan 24

Sonesta Simply Suites Boston Burlington

Burlington

CNY740 total

includes taxes & fees

Jan 17 - Jan 18

Hampton Inn Boston Logan Airport Chelsea

Chelsea

CNY761 total

includes taxes & fees

Jan 19 - Jan 20

Hampton Inn & Suites Boston/Waltham

Waltham

CNY761 total

includes taxes & fees

Jan 18 - Jan 19

DoubleTree by Hilton Boston North Shore

Danvers

CNY761 total

includes taxes & fees

Feb 1 - Feb 2

View all budget hotels

Go beyond your typical stay in Winchester

Apart hotel

Spa

Top landmarks in Winchester

Winter Pond

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 Woburn Bowladrome, 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

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

Encore Boston Harbor

10/10 Excellent

"Spectacular room, loaded with amenities and spotless"

Harborside Inn Of Boston

10/10 Excellent

"Everyone at the hotel was very nice, they greeted me with a smile every time I walked in and out. The hotel is conveniently located and it has a great style/vibe to it. Very good heating for an incredibly cold weekend :) only issue might be their website says they have a dvd player in the room, mine did not."

The Revolution Hotel

10/10 Excellent

"I got the chance to stay at The revolution Hotel for three days and I had a very good experience. The staff are super nice, the room is clean. I don’t have a complaint at all, I really liked my stay there. If I were to travel to Boston again, I will definitely stay at The Revolution Hotel again !"

Frequently asked questions

How much does a hotel room cost in Winchester?

You can find top hotels in Winchester from CNY530 with options to suit your budget and needs. If you're after an affordable hotel in Winchester that meets all of your requirements, set your filters and then sort the results by "Price: low to high".

How can I find deals and earn rewards at Winchester hotels?

Discover great deals on Winchester hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Winchester hotels.

Can I book Winchester hotels with free cancellation?

It's easy to book a refundable Winchester hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some popular hotels in central Winchester?

If you're looking for hotels in central Winchester, check out The Row Hotel at Assembly Row, Autograph Collection and Doubletree By Hilton Boston Logan Airport Chelsea. Travelers love The Row Hotel at Assembly Row, Autograph Collection for its location, as well as the indoor pool, restaurant and bar/lounge this hotel offers. Doubletree By Hilton Boston Logan Airport Chelsea is another popular central hotel with an indoor pool, a restaurant and a bar/lounge. Stay at one of these hotels for easy access to top sights like Harvard University and Harvard Square. Allston and Charlestown are some of the most central neighborhoods for your Winchester vacation.

What accommodations do travelers like in Winchester?

Guests like Harborside Inn Of Boston, Hilton Boston Back Bay 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.

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