Winchester Hotels from S$120

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
24 Nov - 25 Nov
Tomorrow
25 Nov - 26 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Winchester hotels

Lobby sitting area
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4.0 star property
Danvers
8.0 out of 10, Very good, (2236)
"Good place to stay "
United States
Alexandra
The price is S$131
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Boston North Shore
Free continental breakfast
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, (1924)
"Enjoyed our stay"
United States
Christine
The price is S$150
includes taxes & fees
25 Nov - 26 Nov
La Quinta Inn & Suites by Wyndham Boston-Andover
Terrace/patio
Sonesta Select Boston Danvers

Sonesta Select Boston Danvers

3.0 star property
Danvers
8.6 out of 10, Excellent, (1011)
"Great place to stay"
United States
Juanita Diaz
The price is S$157
includes taxes & fees
30 Nov - 1 Dec
Sonesta Select Boston Danvers
Beach
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 star property
Beverly
9.2 out of 10, Wonderful, (1118)
"This hotel was very clean with very comfortable beds and super clean bathrooms! "
United States
Nona
The Wylie Inn and Conference Center at Endicott College
Exterior
Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston

2.5 star property
Andover
8.8 out of 10, Excellent, (1012)
"Kitchen dining area was lovely. Staff were pleasant. The hotel was perfect for our stay."
Canada
Ertug
The price is S$174
includes taxes & fees
27 Nov - 28 Nov
Sonesta ES Suites Andover Boston
Exterior
Nantasket Beach Resort

Nantasket Beach Resort

3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1008)
"Lovely place to stay!"
United States
Patrice
The price is S$188
includes taxes & fees
2 Dec - 3 Dec
Nantasket Beach Resort
Exterior
The Cove At Salem

The Cove At Salem

3.0 star property
Salem
9.4 out of 10, Exceptional, (819)
"Great staff, well decorated modern room!"
United States
Matthew
The price is S$181
includes taxes & fees
30 Nov - 1 Dec
The Cove At Salem
Indoor pool
Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

2.5 star property
Waltham
9.4 out of 10, Exceptional, (1537)
"Clean room, staff was really nice"
United States
Adam
The price is S$125
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn & Suites Boston/Waltham
Daily buffet 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, (1004)
"Clean, friendly, quiet "
United States
Michael
The price is S$127
includes taxes & fees
14 Dec - 15 Dec
Hilton Garden Inn Boston/Waltham
Free daily buffet breakfast
HYATT house Boston/Waltham

HYATT house Boston/Waltham

3.0 star property
Waltham
8.8 out of 10, Excellent, (1054)
"The Staff was great, the room was clean and comfortable and the breakfast was good! "
United States
Meridith
The price is S$143
includes taxes & fees
5 Dec - 6 Dec
HYATT house Boston/Waltham
2 restaurants, breakfast, lunch, dinner served; American cuisine
Hawthorne Hotel

Hawthorne Hotel

3.5 star property
Downtown Salem
9.4 out of 10, Exceptional, (1491)
"Clean rooms, great breakfast and dinner options, and a lovely vintage aesthetic. "
United States
Kiera
Hawthorne Hotel
Restaurant
Embassy Suites by Hilton Boston Waltham

Embassy Suites by Hilton Boston Waltham

3.5 star property
Waltham
8.0 out of 10, Very good, (2628)
"Great check in and great accommodations "
United States
Einav
The price is S$139
includes taxes & fees
14 Dec - 15 Dec
Embassy Suites by Hilton Boston Waltham
Lobby
Best Western Plus Waltham Boston

Best Western Plus Waltham Boston

3.0 star property
Piety Corner
8.2 out of 10, Very good, (1094)
"Room was spotless, staff was helpful "
United States
Zhoe
The price is S$120
includes taxes & fees
30 Nov - 1 Dec
Best Western Plus Waltham Boston
Terrace/patio
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

3.0 star property
Tewksbury
8.8 out of 10, Excellent, (838)
"Great place. "
United States
alex
The price is S$127
includes taxes & fees
5 Dec - 6 Dec
Hilton Garden Inn Tewksbury Andover
1 bedroom, premium bedding, down duvets, pillow-top beds
The Revolution Hotel

The Revolution Hotel

3.5 star property
South End
9.0 out of 10, Wonderful, (2277)
"Great hotel! "
United States
Ashleigh
The price is S$127
includes taxes & fees
26 Nov - 27 Nov
The Revolution Hotel
Restaurant
Hampton Inn & Suites Boston Crosstown Center

Hampton Inn & Suites Boston Crosstown Center

3.0 star property
South End
7.8 out of 10, Good, (1399)
"Clean room & friendly staff. "
United States
Mary
The price is S$133
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn & Suites Boston Crosstown Center
Exterior
Seaport Hotel Boston

Seaport Hotel Boston

4.0 star property
Seaport District
9.6 out of 10, Exceptional, (3728)
"Great location and stay!"
United States
Krithika
The price is S$233
includes taxes & fees
27 Nov - 28 Nov
Seaport Hotel Boston
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, (1366)
"All was perfect, clean room, helpful staff, perfect location "
Canada
ahmed
The price is S$206
includes taxes & fees
21 Dec - 22 Dec
Aloft by Marriott, Boston Seaport District
View from property
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4240)
"Great hotel "
United States
Marlene
The price is S$332
includes taxes & fees
12 Dec - 13 Dec
Omni Boston Hotel at the Seaport
Terrace/patio
Hampton Inn Boston Woburn

Hampton Inn Boston Woburn

2.5 star property
Woburn
9.2 out of 10, Wonderful, (1312)
"Room was spotless, location wonderful. "
United States
Barbara
The price is S$151
includes taxes & fees
6 Dec - 7 Dec
Hampton Inn Boston Woburn
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

Black Friday Sale

Save up to 50% on select hotels
Book now
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

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

The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Fantastic staff especially front desk!! Room was amazing from bed to pillows to spacious etc.. felt secure and safe. Perfect location to walk to everything. Great coffee shops! "
christine 1-night trip
Posted 1 day ago
The Godfrey Hotel Boston

More cheap stays in Winchester

Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

135 2nd Ave Waltham MA
The price is S$125 per night from 21 Dec to 22 Dec
S$125
21 Dec - 22 Dec
includes taxes & fees
9.2/10 Wonderful! (1,528 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.
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