Winchester Hotels from S$105

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Check prices for these dates

Tonight
10 Jan - 11 Jan
Tomorrow
11 Jan - 12 Jan
Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan

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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, (1,371 reviews)
"Very good room and great breakfast!"
United States
Rodrigo
The price is S$148
includes taxes & fees
6 Feb - 7 Feb
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, (1,004 reviews)
"Clean room, great and attentive staff, good breakfast !"
United States
Adriana
The price is S$127
includes taxes & fees
14 Jan - 15 Jan
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, (1,535 reviews)
"Comfortable bed, quiet and great staff"
United States
Shauna
The price is S$134
includes taxes & fees
22 Jan - 23 Jan
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, (1,003 reviews)
"The environment was nice, the room felt new, and the breakfast was very nice. We really enjoyed our stay."
Canada
Jing
The price is S$152
includes taxes & fees
18 Jan - 19 Jan
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, (1,002 reviews)
"Great room off season, great view of the ocean. Have stayed before and will be back!"
United States
Patricia
The price is S$190
includes taxes & fees
25 Jan - 26 Jan
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, (1,001 reviews)
"Clean, convenient location."
United States
Tony
The price is S$194
includes taxes & fees
18 Jan - 19 Jan
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, (1,002 reviews)
"The nicest hotel in the area. "
United States
Edna
The price is S$164
includes taxes & fees
10 Feb - 11 Feb
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 reviews)
"Our second stay there, love it"
United States
Steve
The price is S$408
includes taxes & fees
30 Jan - 31 Jan
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, (3,880 reviews)
"Great Hotel"
United States
Naika
The price is S$177
includes taxes & fees
16 Jan - 17 Jan
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, (1,003 reviews)
"Great place to stay comfortably "
United States
Rene
The price is S$152
includes taxes & fees
25 Jan - 26 Jan
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, (1,001 reviews)
"Friendly and helpful staff, clean hotel and cute decor. Also, a great bar downstairs! "
Canada
Jasmyn
The price is S$130
includes taxes & fees
25 Jan - 26 Jan
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, (1,972 reviews)
"Nice room, free breakfast, staff very joyful "
United States
Kai
The price is S$142
includes taxes & fees
1 Feb - 2 Feb
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, (2,326 reviews)
"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, (1,614 reviews)
"Amazing stay and friendly staff! "
United States
Caterin
The price is S$158
includes taxes & fees
7 Feb - 8 Feb
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, (1,003 reviews)
"Very clean room, quiet, we got the items we needed and had a very comfortable stay for the weekend!"
United States
Alison
The price is S$105
includes taxes & fees
7 Feb - 8 Feb
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, (1,003 reviews)
"Amazing hotel! Cozy lobby, friendly and helpful staff, clean and spacious room, valet parking. All around great stay!"
United States
Sandra
The price is S$183
includes taxes & fees
1 Feb - 2 Feb
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, (1,001 reviews)
"Very friendly staff and close to everything I wanted to see"
United States
Rachel ann
The price is S$145
includes taxes & fees
18 Jan - 19 Jan
Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
Reception
Hotel 1868

Hotel 1868

Hotel 1868
3.5 star property
Agassiz
9.6 out of 10, Exceptional, (1,001 reviews)
"Clean rooms, great gym, friendly and helpful staff."
United States
Jose
The price is S$147
includes taxes & fees
18 Jan - 19 Jan
Hotel 1868
Restaurant
Porter Square Hotel

Porter Square Hotel

Porter Square Hotel
3.0 star property
North Cambridge
9.2 out of 10, Wonderful, (1,002 reviews)
"This was a good place for a stay in a convenient location."
United States
Corey
The price is S$147
includes taxes & fees
25 Jan - 26 Jan
Porter Square Hotel
Desk, laptop workspace, blackout curtains, 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 reviews)
"Good rooms, helpful staff"
United States
Abhir
The price is S$137
includes taxes & fees
17 Jan - 18 Jan
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

Enjoy an outing to Winter Pond during your stay in Winchester. Discover the top-notch restaurants and acclaimed art galleries in this vibrant area.
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
"Nice and quiet. We enjoyed our stay!"
Channa 1-night trip
Posted 17 hours ago
Omni Boston Hotel at the Seaport

More cheap stays in Winchester

Ramada by Wyndham Boston

Ramada by Wyndham Boston

800 Morrissey Blvd Boston MA
The price is S$126 per night from 6 Feb to 7 Feb
S$126
6 Feb - 7 Feb
includes taxes & fees
6.8/10 (1,598 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 traveller data. Two other options for your stay in 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, most hotel bookings are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What are some accommodation options 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 on-site pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors can enjoy all that Winchester has to offer, including the football 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 accommodation options to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
A couple of favourite places to visit are Winter Pond and Middlesex Fells Reservation. Additionally, you'll find TD Garden and Fenway Park in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.
How can I get around Winchester?
To venture out into 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 temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 13 cm of snowfall.

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