Photo by Ana Lei

Winchester hotels from RM348

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Lobby
citizenM Boston Back Bay

citizenM Boston Back Bay

citizenM Boston Back Bay
4.0 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (2140)
Experience urban convenience at this contemporary Back Bay retreat. Just steps from Hynes Convention Centre Station and within walking distance to Fenway Park, Newbury Street, and Northeastern University. Enjoy international cuisine at canteenM after energising in the 24-hour fitness centre.
"Great stay "
United States
Alexander
The price is RM436
RM507 total
includes taxes & fees
6 Jan - 7 Jan 2026
citizenM Boston Back Bay
Premium bedding, in-room safe, iron/ironing board, free WiFi
Found Hotel Boston Common

Found Hotel Boston Common

Found Hotel Boston Common
2.5 star property
Bay Village
8.2 out of 10, Very good, (1269)
Escape to the heart of Boston at this welcoming hotel, steps from Boston Common and Newbury Street. Enjoy free WiFi and helpful concierge services while staying minutes from Boylston Station. Guests praise the clean rooms, prime location, and easy access to popular sights.
"I always like staying here "
United States
Sonia
The price is RM362
RM422 total
includes taxes & fees
24 Dec - 25 Dec
Found Hotel Boston Common
Peruvian cuisine
The Godfrey Hotel Boston

The Godfrey Hotel Boston

The Godfrey Hotel Boston
4.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (4808)
Savour Peruvian cuisine at RUKA Restobar after strolling to Boston Common and New England Aquarium, both within 15 minutes. When day turns to evening, the hotel bar awaits. Fitness enthusiasts will appreciate the 24-hour gym just steps from your room.
"Great place to stay"
United States
Nick A
The price is RM399
RM655 total
includes taxes & fees
24 Dec - 25 Dec
The Godfrey Hotel Boston
In-room safe, blackout curtains, iron/ironing board, free WiFi
Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel
4.0 star property
Back Bay
8.6 out of 10, Excellent, (3916)
Immerse yourself in Boston's historical atmosphere at this boutique hotel. Just steps from Copley Square, enjoy easy access to shopping at Prudential Centre and nearby attractions. After sightseeing, unwind with a drink at the hotel's bar before retiring to your peaceful room.
"Was perfect for my overnight stay in Boston and close to public transportation, Boston Common and Newburry Street!"
United States
Dawn
The price is RM342
RM398 total
includes taxes & fees
25 Dec - 26 Dec
Copley Square Hotel, a FOUND Hotel
Lobby
Hilton Boston Park Plaza

Hilton Boston Park Plaza

Hilton Boston Park Plaza
4.0 star property
Bay Village
8.4 out of 10, Very good, (3116)
Experience elegant comfort in this luxurious hotel just steps from Boston Common and Newbury Street. Enjoy local cuisine at Off the Common restaurant, quick access to Arlington Station, and convenient amenities while exploring nearby Copley Square and historic landmarks.
"Great stay! "
United States
Charles
The price is RM424
RM660 total
includes taxes & fees
3 Jan - 4 Jan 2026
Hilton Boston Park Plaza
Meeting facility
Aloft by Marriott, Boston Seaport District

Aloft by Marriott, Boston Seaport District

Aloft by Marriott, Boston Seaport District
3.0 star property
Seaport District
9.0 out of 10, Wonderful, (1385)
Immerse yourself in Boston's Seaport District at this modern hotel with an indoor pool and fitness centre. Grab refreshments at the café or unwind at the bar. Close to New England Aquarium and Boston Common with convenient access to Logan Airport.
"Room was nice and clean reception staff was very friendly."
United States
Ede
The price is RM403
RM588 total
includes taxes & fees
24 Dec - 25 Dec
Aloft by Marriott, Boston Seaport District
Exterior
Midtown Hotel

Midtown Hotel

Midtown Hotel
2.0 star property
Back Bay
7.4 out of 10, Good, (1011)
Explore Boston from this centrally located hotel near Northeastern University and Symphony Station. Enjoy quick access to Copley Place, Prudential Centre, and Newbury Street within a 10-minute walk. Free WiFi and 24-hour front desk make your city adventure seamless.
"A pleasant hotel, well-located, with friendly service and clean rooms."
United States
Renato Reis
The price is RM422
RM491 total
includes taxes & fees
25 Dec - 26 Dec
Midtown Hotel
Property entrance
Copley House

Copley House

Copley House
3.0 star property
Back Bay
9.0 out of 10, Wonderful, (1940)
Experience Boston's best from this Victorian guesthouse near Copley Square and Northeastern University. Clean rooms with comfortable beds await after exploring Newbury Street or Fenway Park. With 2 transit stations nearby, city adventures are effortless.
"Fantastic place to stay and visit Boston."
United States
Poorvajan
Copley House
Exterior
Hyatt Centric Faneuil Hall Boston

Hyatt Centric Faneuil Hall Boston

Hyatt Centric Faneuil Hall Boston
4.0 star property
Downtown Boston
9.2 out of 10, Wonderful, (1241)
Discover Boston's historic heart at this stylish hotel near Quincy Market and Faneuil Hall. Steps from State St. Station, you'll find Italian dining at Jules on Devonshire and a 24-hour fitness centre. New England Aquarium and Boston Harbour await just 15 minutes away.
"Beautiful view and the staff was amazing "
United States
Cybill
The price is RM444
RM679 total
includes taxes & fees
24 Dec - 25 Dec
Hyatt Centric Faneuil Hall Boston
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, (1003)
"Great stay"
United States
John
The price is RM326
RM498 total
includes taxes & fees
6 Jan - 7 Jan 2026
Staypineapple, A Delightful Hotel, South End
Lobby
citizenM Boston North Station

citizenM Boston North Station

citizenM Boston North Station
4.0 star property
West End
9.4 out of 10, Exceptional, (4195)
Steps from North Station, this hotel puts TD Garden and Museum of Science within a 15-minute walk. Enjoy international cuisine at canteenM or visit the 24-hour fitness centre. Quincy Market and Massachusetts General Hospital are nearby, with Haymarket Station just 7 minutes away.
"Staff was super friendly and the room was perfect! "
United States
Jennifer
The price is RM436
RM508 total
includes taxes & fees
1 Jan - 2 Jan 2026
citizenM Boston North Station
Meeting facility
Moxy Boston Downtown

Moxy Boston Downtown

Moxy Boston Downtown
3.5 star property
Bay Village
8.8 out of 10, Excellent, (1010)
Vibrant city centre hotel within a 10-minute walk of Boston Common and Newbury Street. Unwind at the bar after exploring nearby Copley Square or squeeze in a workout at the 24-hour fitness centre. Just 2 minutes from Boylston Station for effortless city adventures.
"Great amenities and staff- perfect location "
United States
Molly
The price is RM322
RM540 total
includes taxes & fees
15 Jan - 16 Jan 2026
Moxy Boston Downtown
Premium bedding, in-room safe, blackout curtains, iron/ironing board
Hyatt Regency Boston

Hyatt Regency Boston

Hyatt Regency Boston
4.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (1728)
Experience city centre convenience at this quiet retreat, just 3 minutes from Chinatown Station. Guests love the spectacular city views and easy access to Boston Common. Enjoy the indoor pool and health club after exploring nearby Faneuil Hall Marketplace.
"Amazing room, friendly staff"
United States
Ryan
The price is RM518
RM745 total
includes taxes & fees
28 Dec - 29 Dec
Hyatt Regency Boston
Premium bedding, down duvets, pillow-top beds, in-room safe
The Revolution Hotel

The Revolution Hotel

The Revolution Hotel
3.5 star property
South End
9.0 out of 10, Wonderful, (2347)
Explore Boston with ease from this contemporary hotel, just minutes from Arlington Station and Newbury Street. Enjoy comfortable beds and the on-site Cosmica restaurant for dinner, plus a stylish bar. The helpful staff and nearby Copley Place enhance your city adventure.
"Very nice hotel and location was excellent."
United States
Laura
The Revolution Hotel
Front of property
YOTEL Boston

YOTEL Boston

YOTEL Boston
4.0 star property
Seaport District
8.6 out of 10, Excellent, (2365)
Enjoy stunning skyline views from this modern Boston hotel's rooftop terrace. Located just steps from Boston Harbour and a 13-minute walk to the Aquarium, guests praise the restaurant, 2 bars, and 24-hour fitness centre. Comfortable beds await after exploring nearby attractions.
"Good hotel to stay "
United States
Luis
The price is RM391
RM646 total
includes taxes & fees
28 Dec - 29 Dec
YOTEL Boston
Terrace/patio
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4320)
Immerse yourself in sophisticated comfort at this Seaport District gem, just a 15-minute walk from Boston Convention Centre and Flynn Cruiseport. Enjoy 4 restaurants, 2 bars, and an outdoor pool with poolside service after indulging in rejuvenating spa treatments.
"Awesome stay. "
United States
Xavier
The price is RM599
RM864 total
includes taxes & fees
24 Dec - 25 Dec
Omni Boston Hotel at the Seaport
View from property
AC Hotel by Marriott Boston Downtown

AC Hotel by Marriott Boston Downtown

AC Hotel by Marriott Boston Downtown
3.5 star property
South End
8.8 out of 10, Excellent, (1003)
This stylish hotel offers a 24-hour fitness centre and restaurant with bar, just minutes from Broadway Station. Explore Boston Common and Copley Square nearby or enjoy the outdoor terrace. Guests praise the convenient location and exceptional staff.
"Spotless, beautiful modern furniture, great mattress "
United States
Afroditi
The price is RM465
RM660 total
includes taxes & fees
26 Dec - 27 Dec
AC Hotel by Marriott Boston Downtown
Front of property
Harborside Inn Of Boston

Harborside Inn Of Boston

Harborside Inn Of Boston
4.0 star property
Government Center
9.2 out of 10, Wonderful, (6090)
Walking distance to Faneuil Hall Marketplace and New England Aquarium, this tranquil hotel sits steps from Aquarium Station. Enjoy the on-site restaurant, bar, and free WiFi while exploring nearby Quincy Market and Boston Harbour.
"Great location and a very nice hotel."
United States
Alan
The price is RM436
RM508 total
includes taxes & fees
24 Dec - 25 Dec
Harborside Inn Of Boston
Bar (on property)
Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District
3.0 star property
Seaport District
9.4 out of 10, Exceptional, (2229)
Experience Boston's vibrant Seaport District at this Art Deco hotel with rooftop terrace, just a short walk from the Exhibition Centre and Flynn Cruiseport. Enjoy breakfast at the café, stay fit at the gym, and relax with drinks at the bar.
"Very nice hotel and great location"
United States
Ann
The price is RM550
RM641 total
includes taxes & fees
28 Dec - 29 Dec
Hyatt Place Boston/Seaport District
Property entrance
The Verb Hotel

The Verb Hotel

The Verb Hotel
3.5 star property
Fenway–Kenmore
9.6 out of 10, Exceptional, (1965)
Within walking distance of Fenway Park and Northeastern University, this music-themed hotel offers a refreshing outdoor pool with poolside bar. Japanese cuisine at Hojoko restaurant and tranquil garden spaces create a fun yet relaxing atmosphere praised by travellers.
"Breakfast very limited, but otherwise nice place to stay."
United States
Gemma
The price is RM363
RM612 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Verb Hotel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Great place to stay"
Nick A 4-night trip
Posted 20 hours ago
The Godfrey Hotel Boston

More cheap stays in Winchester

Ramada by Wyndham Boston

Ramada by Wyndham Boston

800 Morrissey Blvd Boston MA
The price is RM322 per night from 31 Dec to 1 Jan
RM322
RM375 total
31 Dec - 1 Jan 2026
includes taxes & fees
6.6/10 (1,587 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 Omni Boston Hotel at the Seaport and Hilton Boston Back Bay. 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. 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, Encore Boston Harbor and Harvard Square 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 Encore Boston Harbor 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.

Explore a world of travel with Expedia