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Top hotels and accommodation in Winchester

Exterior
The Westin Boston Seaport District

The Westin Boston Seaport District

4.0 star property
Seaport District
9.2 out of 10, Wonderful, (2312)
"Nice hotel and great location."
United States
James Earl
The price is AU$251
includes taxes & fees
22 Dec - 23 Dec
The Westin Boston Seaport District
Terrace/patio
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4264)
"Awesome stay. "
United States
Xavier
The price is AU$364
includes taxes & fees
18 Dec - 19 Dec
Omni Boston Hotel at the Seaport
Peruvian cuisine
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (4763)
"Great location. "
United States
Veronica
The price is AU$225
includes taxes & fees
21 Dec - 22 Dec
The Godfrey Hotel Boston
Lobby
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4.0 star property
Bay Village
8.4 out of 10, Very good, (3110)
"Great stay! "
United States
Charles
The price is AU$257
includes taxes & fees
18 Dec - 19 Dec
Hilton Boston Park Plaza
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, (3903)
"Great for a short stay option. We stayed 2 days and it was perfect for our needs. "
United States
Rocco
The price is AU$140
includes taxes & fees
22 Dec - 23 Dec
Copley Square Hotel, a FOUND Hotel
Terrace/patio
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3.0 star property
Seaport District
9.2 out of 10, Wonderful, (2694)
"Good room, fantastic breakfast all very clean."
United States
Andres
The price is AU$192
includes taxes & fees
1 Jan - 2 Jan 2026
Hampton Inn Boston Seaport District
Meeting facility
Moxy Boston Downtown

Moxy Boston Downtown

3.5 star property
Bay Village
8.8 out of 10, Excellent, (1005)
"Great place to stay. Good location, good service, nice rooms, very good price"
United States
Rigoberto
The price is AU$200
includes taxes & fees
25 Dec - 26 Dec
Moxy Boston Downtown
Meeting facility
Aloft by Marriott, Boston Seaport District

Aloft by Marriott, Boston Seaport District

3.0 star property
Seaport District
9.0 out of 10, Wonderful, (1369)
"Room was nice and clean reception staff was very friendly."
United States
Ede
The price is AU$224
includes taxes & fees
21 Dec - 22 Dec
Aloft by Marriott, Boston Seaport District
View from room
InterContinental Boston by IHG

InterContinental Boston by IHG

5.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (1007)
"Beautiful hotel, great location, gracious staff."
United States
Amalia
The price is AU$350
includes taxes & fees
22 Dec - 23 Dec
InterContinental Boston by IHG
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, (2202)
"Excellent hotel"
United States
Krasimira
The price is AU$246
includes taxes & fees
11 Dec - 12 Dec
Hyatt Place Boston/Seaport District
Suite (VIP)
Hyatt Regency Boston

Hyatt Regency Boston

4.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (1698)
"Clean room and great amenities"
United States
Franklin
The price is AU$267
includes taxes & fees
14 Dec - 15 Dec
Hyatt Regency Boston
Front of property
Harborside Inn Of Boston

Harborside Inn Of Boston

4.0 star property
Government Center
9.2 out of 10, Wonderful, (6028)
"Great location and comfortable rooms"
United States
Matthew
The price is AU$188
includes taxes & fees
24 Dec - 25 Dec
Harborside Inn Of Boston
Executive Suite, 1 King Bed
Element by Marriott, Boston Seaport District

Element by Marriott, Boston Seaport District

3.0 star property
Seaport District
9.0 out of 10, Wonderful, (1000)
"Room was clean and comfortable. Staff was friendly and helpful."
United States
Michael
The price is AU$211
includes taxes & fees
21 Dec - 22 Dec
Element by Marriott, Boston Seaport District
Exterior
DoubleTree by Hilton Boston - Downtown

DoubleTree by Hilton Boston - Downtown

4.0 star property
Bay Village
8.8 out of 10, Excellent, (1005)
"Staff was excellent "
United States
Jenifer
The price is AU$186
includes taxes & fees
15 Dec - 16 Dec
DoubleTree by Hilton Boston - Downtown
Breakfast, lunch, dinner served; American cuisine
The Dagny Boston

The Dagny Boston

4.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (6806)
"Nice place for a quick stay"
United States
Mary
The price is AU$304
includes taxes & fees
21 Dec - 22 Dec
The Dagny Boston
Lobby
citizenM Boston North Station

citizenM Boston North Station

4.0 star property
West End
9.2 out of 10, Wonderful, (4124)
"Great hotel /location "
United States
Sofia
The price is AU$188
includes taxes & fees
24 Dec - 25 Dec
citizenM Boston North Station
Exterior
Sheraton Boston, a Marriott Hotel

Sheraton Boston, a Marriott Hotel

4.0 star property
Back Bay
8.6 out of 10, Excellent, (1736)
"Excellent hotel very nice "
United States
PAUL
The price is AU$244
includes taxes & fees
21 Dec - 22 Dec
Sheraton Boston, a Marriott Hotel
Exterior
Boston Marriott Copley Place

Boston Marriott Copley Place

4.0 star property
Back Bay
9.2 out of 10, Wonderful, (1712)
"Great hotel"
United States
Farhad
The price is AU$331
includes taxes & fees
21 Dec - 22 Dec
Boston Marriott Copley Place
Front of property – evening/night
Omni Parker House

Omni Parker House

4.5 star property
Downtown Boston
9.0 out of 10, Wonderful, (3221)
"Staff and amenities were great"
United States
Maya
The price is AU$349
includes taxes & fees
15 Dec - 16 Dec
Omni Parker House
Lobby
Hilton Boston Back Bay

Hilton Boston Back Bay

4.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (1236)
"Friendly staff, great location and church on Sunday."
United States
Jennifer
The price is AU$293
includes taxes & fees
21 Dec - 22 Dec
Hilton Boston Back Bay
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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Clean , quiet and comfy. Gods guest service. "
Lirio 3-night trip
Posted 20 hours ago
Harborside Inn Of Boston

More cheap accommodation in Winchester

Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

135 2nd Ave Waltham MA
The price is AU$144 per night from 21 Dec to 22 Dec
AU$144
21 Dec - 22 Dec
includes taxes & fees
9.2/10 Wonderful! (1,557 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
Located 7.1 mi (11.4 km) from the heart of Winchester, citizenM Boston North Station is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Omni Boston Hotel at the Seaport and The Revolution Hotel. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Cozy Salem Getaway. Historic Home Near All the Sights: This holiday home rental outside of Winchester offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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. Offers 4 restaurants, an outdoor pool and a full-service spa. Seaport Hotel Boston and Hilton Boston Logan Airport 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. Fenway Park, Harvard Square and TD Garden 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 Fenway Park and Harvard Square 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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