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Find hotels in Winchester, MA from ₩118,156

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Our top choices for Winchester hotels

Terrace/patio
Hampton Inn Boston Woburn

Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.0 out of 10, Wonderful, (1370)
"Very good room and great breakfast!"
United States
Rodrigo
The price is ₩149,754
₩167,276 total
includes taxes & fees
Feb 6 - Feb 7
Hampton Inn Boston Woburn
Free daily buffet breakfast
Best Western Plus New Englander

Best Western Plus New Englander

Best Western Plus New Englander
2.5 star property
Woburn
8.6 out of 10, Excellent, (1004)
"Clean room, great and attentive staff, good breakfast !"
United States
Adriana
The price is ₩127,996
₩142,971 total
includes taxes & fees
Jan 20 - Jan 21
Best Western Plus New Englander
Indoor pool
Sheraton Boston Needham Hotel

Sheraton Boston Needham Hotel

Sheraton Boston Needham Hotel
3.5 star property
Needham
8.8 out of 10, Excellent, (1531)
"Comfortable bed, quiet and great staff"
United States
Shauna
The price is ₩135,521
₩151,378 total
includes taxes & fees
Jan 22 - Jan 23
Sheraton Boston Needham Hotel
Exterior
Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
Watertown
9.4 out of 10, Exceptional, (1001)
"The environment was nice, the room felt new, and the breakfast was very nice. We really enjoyed our stay."
Canada
Jing
The price is ₩153,320
₩171,258 total
includes taxes & fees
Jan 18 - Jan 19
Hampton Inn & Suites Watertown Boston
View from property
Nantasket Beach Resort

Nantasket Beach Resort

Nantasket Beach Resort
3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1008)
"Great room off season, great view of the ocean. Have stayed before and will be back!"
United States
Patricia
The price is ₩161,045
₩213,774 total
includes taxes & fees
Jan 25 - Jan 26
Nantasket Beach Resort
Restaurant
Hilton Garden Inn Boston Brookline, MA

Hilton Garden Inn Boston Brookline, MA

Hilton Garden Inn Boston Brookline, MA
3.0 star property
Brookline
9.0 out of 10, Wonderful, (1000)
"Clean, convenient location."
United States
Tony
The price is ₩195,686
₩218,581 total
includes taxes & fees
Jan 25 - Jan 26
Hilton Garden Inn Boston Brookline, MA
Courtyard
Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston
2.5 star property
Andover
8.8 out of 10, Excellent, (1001)
"The nicest hotel in the area. "
United States
Edna
The price is ₩172,302
₩192,462 total
includes taxes & fees
Jan 19 - Jan 20
Sonesta ES Suites Andover Boston
Terrace/patio
The Whitney Hotel

The Whitney Hotel

The Whitney Hotel
4.0 star property
Beacon Hill
9.6 out of 10, Exceptional, (501)
"Our second stay there, love it"
United States
Steve
The price is ₩394,848
₩459,800 total
includes taxes & fees
Jan 29 - Jan 30
The Whitney Hotel
Lobby sitting area
The Arcadian Hotel

The Arcadian Hotel

The Arcadian Hotel
3.5 star property
Brookline
8.0 out of 10, Very Good, (3878)
"Great Hotel"
United States
Naika
The price is ₩134,482
₩198,736 total
includes taxes & fees
Jan 16 - Jan 17
The Arcadian Hotel
Indoor pool
Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG
2.5 star property
Chelmsford
8.8 out of 10, Excellent, (1002)
"Great place to stay comfortably "
United States
Rene
The price is ₩130,448
₩145,710 total
includes taxes & fees
Jan 15 - Jan 16
Holiday Inn Express Chelmsford by IHG
Interior
Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End
3.0 star property
South End
9.0 out of 10, Wonderful, (1000)
"Friendly and helpful staff, clean hotel and cute decor. Also, a great bar downstairs! "
Canada
Jasmyn
The price is ₩128,998
₩192,338 total
includes taxes & fees
Jan 19 - Jan 20
Staypineapple, A Delightful Hotel, South End
Coffee service
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover
3.0 star property
Andover
8.2 out of 10, Very Good, (1969)
"Nice room, free breakfast, staff very joyful "
United States
Kai
The price is ₩143,493
₩160,281 total
includes taxes & fees
Feb 1 - Feb 2
La Quinta Inn & Suites by Wyndham Boston-Andover
Exterior
Lakeside Inn

Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
7.6 out of 10, Good, (2324)
"Another great stay!"
United States
Brian
Lakeside Inn
Exterior
Hyatt Place Boston/Medford

Hyatt Place Boston/Medford

Hyatt Place Boston/Medford
3.0 star property
Medford
8.4 out of 10, Very Good, (1612)
"Amazing stay and friendly staff! "
United States
Caterin
The price is ₩159,271
₩177,905 total
includes taxes & fees
Jan 25 - Jan 26
Hyatt Place Boston/Medford
Daily full breakfast (USD 17 per person)
Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham
3.0 star property
Waltham
8.8 out of 10, Excellent, (1002)
"clean room, good location, great bathroom amenities, good staff"
United States
Sanjeev
The price is ₩105,779
₩118,156 total
includes taxes & fees
Feb 6 - Feb 7
Hilton Garden Inn Boston/Waltham
Lobby
Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
3.0 star property
Spring Hill
9.6 out of 10, Exceptional, (1016)
"Amazing hotel! Cozy lobby, friendly and helpful staff, clean and spacious room, valet parking. All around great stay!"
United States
Sandra
The price is ₩195,759
₩218,662 total
includes taxes & fees
Feb 8 - Feb 9
Cambria Hotel Boston Somerville
Lobby sitting area
Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
2.5 star property
Chelsea
9.0 out of 10, Wonderful, (1001)
"Very friendly staff and close to everything I wanted to see"
United States
Rachel ann
The price is ₩146,609
₩163,762 total
includes taxes & fees
Jan 11 - Jan 12
Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
Reception
Hotel 1868

Hotel 1868

Hotel 1868
3.5 star property
Agassiz
9.4 out of 10, Exceptional, (1000)
"Clean rooms, great gym, friendly and helpful staff."
United States
Jose
The price is ₩153,965
₩178,523 total
includes taxes & fees
Jan 19 - Jan 20
Hotel 1868
Restaurant
Porter Square Hotel

Porter Square Hotel

Porter Square Hotel
3.0 star property
North Cambridge
9.2 out of 10, Wonderful, (1001)
"This was a good place for a stay in a convenient location."
United States
Corey
The price is ₩143,036
₩165,850 total
includes taxes & fees
Jan 18 - Jan 19
Porter Square Hotel
Desk, laptop workspace, blackout drapes, iron/ironing board
Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington
2.0 star property
Burlington
9.0 out of 10, Wonderful, (158)
"Good rooms, helpful staff"
United States
Abhir
The price is ₩137,552
₩153,646 total
includes taxes & fees
Jan 16 - Jan 17
Sonesta Simply Suites Boston Burlington
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

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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"The location is great and the staff was helpful "
Shawnah 3-night trip
Posted 21 hours ago
Harborside Inn Of Boston

More cheap stays in Winchester

Ramada by Wyndham Boston

Ramada by Wyndham Boston

800 Morrissey Blvd Boston MA
The price is ₩124,070 per night from Jan 31 to Feb 1
₩124,070
₩144,480 total
Jan 31 - Feb 1
includes taxes & fees
6.8/10 (1,597 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
Located 7.7 mi (12.4 km) from the heart of Winchester, Harborside Inn Of Boston is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Hilton Boston Back Bay and Omni Boston Hotel at the Seaport. See all available top hotels, or 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, 3-minute walk from Boston Convention and Exhibition Center. Provides 4 restaurants, an outdoor pool, and a full-service spa. Seaport Hotel Boston and The Langham, Boston 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. TD Garden, Fenway Park, and Encore Boston Harbor 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 TD Garden and Fenway Park 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.