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Check prices for these dates

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

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Our top choices for Winchester hotels

Lobby

Hilton Boston Park Plaza

Hilton Boston Park Plaza
4.0 star property
Bay Village
8.4 out of 10, Very good, (3,109 reviews)
"Amazing hotel, centrally located "
United States
Karen
The price is AU$220
includes taxes & fees
15 Feb - 16 Feb
Hilton Boston Park Plaza
International cuisine

citizenM Boston Back Bay

citizenM Boston Back Bay
4.0 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (2,236 reviews)
"An amazing hotel, clean, nice staff, great service "
United States
Tamar
The price is AU$185
includes taxes & fees
25 Jan - 26 Jan
citizenM Boston Back Bay
In-room safe, blackout curtains, 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, (3,913 reviews)
"Great location, clean and comfy room, friendly staff."
United States
Zachary
The price is AU$130
includes taxes & fees
4 Feb - 5 Feb
Copley Square Hotel, a FOUND Hotel
Premium bedding, down duvets, pillow-top beds, in-room safe

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4,417 reviews)
"Good place to stay "
United States
Richard
The price is AU$272
includes taxes & fees
1 Feb - 2 Feb
Omni Boston Hotel at the Seaport
Lobby sitting area

The Revolution Hotel

The Revolution Hotel
3.5 star property
South End
9.0 out of 10, Wonderful, (2,401 reviews)
"Great stay! Clean room, kind staff, and excellent location. Would stay here again and would recommend "
United States
Mia Lian
The price is AU$114
includes taxes & fees
25 Jan - 26 Jan
The Revolution Hotel
Peruvian cuisine

The Godfrey Hotel Boston

The Godfrey Hotel Boston
4.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (4,871 reviews)
"Great location, nice staff"
United States
Zhong
The price is AU$240
includes taxes & fees
25 Jan - 26 Jan
The Godfrey Hotel Boston
Standard Room, 1 Queen Bed

Found Hotel Boston Common

Found Hotel Boston Common
2.5 star property
Bay Village
8.4 out of 10, Very good, (1,291 reviews)
"Nice place to stay!"
United States
Brenda
The price is AU$124
includes taxes & fees
1 Feb - 2 Feb
Found Hotel Boston Common
Executive Room, Terrace | Living area

Hyatt Regency Boston

Hyatt Regency Boston
4.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (1,801 reviews)
"Amazing place to stay! "
United States
Yohlman
The price is AU$272
includes taxes & fees
12 Feb - 13 Feb
Hyatt Regency Boston
Lobby

Aloft by Marriott, Boston Seaport District

Aloft by Marriott, Boston Seaport District
3.0 star property
Seaport District
9.0 out of 10, Wonderful, (1,402 reviews)
"Clean room, great bar and breakfast options and good location. "
United States
Bianca
The price is AU$215
includes taxes & fees
23 Jan - 24 Jan
Aloft by Marriott, Boston Seaport District
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
17 Feb - 18 Feb
Staypineapple, A Delightful Hotel, South End
Exterior

Seaport Hotel Boston

Seaport Hotel Boston
4.0 star property
Seaport District
9.6 out of 10, Exceptional, (3,925 reviews)
"Great accommodations and friendly staff!"
United States
Nicholas
The price is AU$232
includes taxes & fees
25 Jan - 26 Jan
Seaport Hotel Boston
Rooftop terrace

YOTEL Boston

YOTEL Boston
4.0 star property
Seaport District
8.6 out of 10, Excellent, (2,401 reviews)
"Great stay overall! "
United States
Lourdes
The price is AU$238
includes taxes & fees
23 Jan - 24 Jan
YOTEL Boston
Desk, laptop workspace, blackout curtains, iron/ironing board

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta
2.0 star property
Back Bay
7.6 out of 10, Good, (1,003 reviews)
"Very clean and nice rooms. The hotel staff is also very kind."
United States
James
The price is AU$170
includes taxes & fees
1 Feb - 2 Feb
The Midtown Hotel MOD Collection by Sonesta
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, (2,281 reviews)
"Absolutely spotless with great staff, comfortable beds, fun location"
United States
Sarah
The price is AU$234
includes taxes & fees
24 Jan - 25 Jan
Hyatt Place Boston/Seaport District
Lobby

citizenM Boston North Station

citizenM Boston North Station
4.0 star property
West End
9.4 out of 10, Exceptional, (4,295 reviews)
"Great location and great staff"
United States
Anthony
The price is AU$201
includes taxes & fees
25 Jan - 26 Jan
citizenM Boston North Station
Serves breakfast, lunch and dinner

Moxy Boston Downtown

Moxy Boston Downtown
3.5 star property
Bay Village
8.8 out of 10, Excellent, (1,020 reviews)
"Clean room, great atmosphere, bar was nice ! Will definitely stay again !"
United States
Denise
The price is AU$215
includes taxes & fees
1 Feb - 2 Feb
Moxy Boston Downtown
Lobby

The Westin Boston Seaport District

The Westin Boston Seaport District
4.0 star property
Seaport District
9.2 out of 10, Wonderful, (2,380 reviews)
"Great staff, excellent room."
United States
Wayne
The price is AU$368
includes taxes & fees
16 Feb - 17 Feb
The Westin Boston Seaport District
Courtyard

DoubleTree by Hilton Boston - Downtown

DoubleTree by Hilton Boston - Downtown
4.0 star property
Bay Village
8.8 out of 10, Excellent, (1,006 reviews)
"Great staff, comfortable beds"
United States
Jeffrey
The price is AU$176
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Boston - Downtown
Front of property

Harborside Inn Of Boston

Harborside Inn Of Boston
4.0 star property
Government Center
9.2 out of 10, Wonderful, (6,162 reviews)
"great place to stay! "
United States
Jessica
The price is AU$186
includes taxes & fees
25 Jan - 26 Jan
Harborside Inn Of Boston
Breakfast, lunch, dinner served; American cuisine

The Dagny Boston

The Dagny Boston
4.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (6,992 reviews)
"Beautiful hotel, great location, very friendly and helpful staff!"
United States
Jeffrey
The price is AU$310
includes taxes & fees
22 Jan - 23 Jan
The Dagny Boston
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

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Everything was perfect. Very clean, perfect location. Great pool. Amazing staff. Will definitely go again. "
Jose 2-night trip
Posted 13 hours ago
Seaport Hotel Boston

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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