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Check prices for these dates

Tonight
20 Jan - 21 Jan
Tomorrow
21 Jan - 22 Jan
This weekend
23 Jan - 25 Jan
Next weekend
30 Jan - 1 Feb

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Our top choices for Winchester hotels

Terrace/patio

Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.0 out of 10, Wonderful, (1,375 reviews)
"Very good room and great breakfast!"
United States
Rodrigo
The price is AU$176
includes taxes & fees
7 Feb - 8 Feb
Hampton Inn Boston Woburn
Exterior

Hilton Boston/Woburn

Hilton Boston/Woburn
3.5 star property
Woburn
8.4 out of 10, Very good, (1,205 reviews)
"Good time great restaurant "
United States
Jeremy
The price is AU$189
includes taxes & fees
25 Jan - 26 Jan
Hilton Boston/Woburn
Lobby

Hampton Inn Boston Bedford Burlington

Hampton Inn Boston Bedford Burlington
2.5 star property
Billerica
9.2 out of 10, Wonderful, (1,005 reviews)
"Staff very pleasant, clean room"
United States
Jean
The price is AU$162
includes taxes & fees
30 Jan - 31 Jan
Hampton Inn Boston Bedford Burlington
Exterior

Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
Watertown
9.4 out of 10, Exceptional, (1,012 reviews)
"Clean room, spacious, good breakfast, nice staff!"
United States
Carolyn
The price is AU$190
includes taxes & fees
1 Feb - 2 Feb
Hampton Inn & Suites Watertown Boston
Indoor pool

Sheraton Boston Needham Hotel

Sheraton Boston Needham Hotel
3.5 star property
Needham
8.8 out of 10, Excellent, (1,545 reviews)
"Great stay! Loved the location and staff was wonderful. Great gym. "
United States
Andrew
The price is AU$155
includes taxes & fees
19 Feb - 20 Feb
Sheraton Boston Needham Hotel
Courtyard

Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston
2.5 star property
Andover
8.8 out of 10, Excellent, (1,006 reviews)
"Friendly staff, clean rooms, breakfast wasn’t bad, and maybe updates on the bathroom may be needed; overall great stay! "
United States
Vighas
The price is AU$173
includes taxes & fees
15 Feb - 16 Feb
Sonesta ES Suites Andover Boston
View from property

Nantasket Beach Resort

Nantasket Beach Resort
3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1,005 reviews)
"Great room off season, great view of the ocean. Have stayed before and will be back!"
United States
Patricia
The price is AU$231
includes taxes & fees
22 Jan - 23 Jan
Nantasket Beach Resort
Lobby sitting area

The Arcadian Hotel

The Arcadian Hotel
3.5 star property
Brookline
8.0 out of 10, Very good, (3,895 reviews)
"Staff was courteous, hotel was in a good location "
United States
Jill
The price is AU$204
includes taxes & fees
23 Jan - 24 Jan
The Arcadian Hotel
Coffee service

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, (1,986 reviews)
"Great stay ! "
United States
Gabby
The price is AU$163
includes taxes & fees
8 Feb - 9 Feb
La Quinta Inn & Suites by Wyndham Boston-Andover
Exterior

Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
7.6 out of 10, Good, (2,331 reviews)
"Another great stay!"
United States
Brian
Lakeside Inn
Lobby

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 AU$211
includes taxes & fees
10 Feb - 11 Feb
Cambria Hotel Boston Somerville
Exterior

Hyatt Place Boston/Medford

Hyatt Place Boston/Medford
3.0 star property
Medford
8.4 out of 10, Very good, (1,627 reviews)
"Great place!"
United States
EDILAINE
The price is AU$183
includes taxes & fees
29 Jan - 30 Jan
Hyatt Place Boston/Medford
Interior

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End
3.0 star property
South End
9.0 out of 10, Wonderful, (1,004 reviews)
"We've been to several Staypineapple hotels and they're always great. Clean rooms with comfortable beds and nice little extras that make the stay more pleasant."
Canada
Jan S
The price is AU$154
includes taxes & fees
8 Feb - 9 Feb
Staypineapple, A Delightful Hotel, South End
Terrace/patio

The Whitney Hotel

The Whitney Hotel
4.0 star property
Beacon Hill
9.6 out of 10, Exceptional, (504 reviews)
"Our second stay there, love it"
United States
Steve
The price is AU$473
includes taxes & fees
5 Feb - 6 Feb
The Whitney Hotel
Daily full breakfast (USD 17 per person)

Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham
3.0 star property
Waltham
8.8 out of 10, Excellent, (1,001 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 AU$135
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Boston/Waltham
Lobby sitting area

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
3.0 star property
Chelsea
9.0 out of 10, Wonderful, (1,002 reviews)
"Room was clean and staff was very friendly and helpful. Will stay again. "
United States
Sonia
The price is AU$168
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
Lobby

Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham
2.5 star property
Waltham
9.4 out of 10, Exceptional, (1,618 reviews)
"Great hotel, very polite staff!"
United States
Cantay
The price is AU$149
includes taxes & fees
31 Jan - 1 Feb
Hampton Inn & Suites Boston/Waltham
Restaurant

Porter Square Hotel

Porter Square Hotel
3.0 star property
North Cambridge
9.2 out of 10, Wonderful, (1,000 reviews)
"This was a good place for a stay in a convenient location."
United States
Corey
The price is AU$184
includes taxes & fees
27 Jan - 28 Jan
Porter Square Hotel
Exterior

La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville
3.0 star property
Assembly Square
7.6 out of 10, Good, (3,139 reviews)
"Clean room, great location, courteous staff and an inexpensive option to stay the night before an early morning flight out of Logan. "
United States
Daniel
The price is AU$133
includes taxes & fees
25 Jan - 26 Jan
La Quinta Inn & Suites by Wyndham Boston Somerville
Reception

Hotel 1868

Hotel 1868
3.5 star property
Agassiz
9.6 out of 10, Exceptional, (1,001 reviews)
"Great place"
United States
Akhil
The price is AU$171
includes taxes & fees
1 Feb - 2 Feb
Hotel 1868
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

Recent Reviews in Winchester

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Room was spotless and beautiful. Entire facility is top notch."
Christina 2-night trip
Posted 6 hours ago
Encore Boston Harbor

More cheap accommodation in Winchester

Ramada by Wyndham Boston

Ramada by Wyndham Boston

800 Morrissey Blvd Boston MA
The price is AU$147 per night from 26 Jan to 27 Jan
AU$147
26 Jan - 27 Jan
includes taxes & fees
6.8/10 (1,608 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.
What are some of the best holiday rentals that Winchester has to offer?
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi: This holiday home rental outside of Winchester is located in the city centre, and offers a balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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, 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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