Find hotels in Winchester, MA from ฿2,804

  • 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
20 Feb - 21 Feb
Tomorrow
21 Feb - 22 Feb
This weekend
20 Feb - 22 Feb
Next weekend
27 Feb - 1 Mar

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Exterior

Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.2 out of 10, Wonderful, (1,390 reviews)
"Decent hotel "
United States
Patricia
The price is ฿3,545
฿3,960 total
includes taxes & fees
8 Mar - 9 Mar
Hampton Inn Boston Woburn
Exterior

Hilton Boston/Woburn

Hilton Boston/Woburn
3.5 star property
Woburn
8.6 out of 10, Excellent, (1,226 reviews)
"The staff was excellent and very friendly. The room and pool were great!"
United States
Elizabeth
The price is ฿3,800
฿4,245 total
includes taxes & fees
27 Feb - 28 Feb
Hilton Boston/Woburn
Lobby sitting area

Residence Inn by Marriott Boston Natick

Residence Inn by Marriott Boston Natick
3.0 star property
Natick
9.6 out of 10, Exceptional, (729 reviews)
"Yes, it was clean and the staff was very helpful and friendly. "
United States
karen
The price is ฿4,387
฿4,901 total
includes taxes & fees
27 Feb - 28 Feb
Residence Inn by Marriott Boston Natick
Exterior

Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
Watertown
9.4 out of 10, Exceptional, (1,007 reviews)
"Friendly staff, good free breakfast included!"
Canada
kennedy
The price is ฿3,717
฿4,152 total
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn & Suites Watertown Boston
Lobby

Hampton Inn Boston Bedford Burlington

Hampton Inn Boston Bedford Burlington
2.5 star property
Billerica
9.2 out of 10, Wonderful, (1,001 reviews)
"Nice place to stay "
United States
Stacey
The price is ฿2,780
฿3,105 total
includes taxes & fees
27 Feb - 28 Feb
Hampton Inn Boston Bedford Burlington
Indoor pool

Sheraton Boston Needham Hotel

Sheraton Boston Needham Hotel
3.5 star property
Needham
8.8 out of 10, Excellent, (1,568 reviews)
"wonderful, pet friendly (we came with a cat), clean, centrally located hotel! Truly enjoyed our stay. "
United States
Daniela
The price is ฿3,453
฿3,857 total
includes taxes & fees
28 Feb - 1 Mar
Sheraton Boston Needham Hotel
Terrace/patio

The Whitney Hotel

The Whitney Hotel
4.0 star property
Beacon Hill
9.6 out of 10, Exceptional, (519 reviews)
"Our second stay there, love it"
United States
Steve
The price is ฿8,707
฿10,139 total
includes taxes & fees
22 Feb - 23 Feb
The Whitney Hotel
Lobby sitting area

Arcadian Hotel

Arcadian Hotel
3.5 star property
Coolidge Corner
8.0 out of 10, Very good, (3,905 reviews)
"Staff was courteous, hotel was in a good location "
United States
Jill
The price is ฿3,546
฿5,003 total
includes taxes & fees
1 Mar - 2 Mar
Arcadian Hotel
View from property

Nantasket Beach Resort

Nantasket Beach Resort
3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1,006 reviews)
"Front desk staff was great"
United States
John
The price is ฿3,706
฿4,867 total
includes taxes & fees
26 Feb - 27 Feb
Nantasket Beach Resort
Terrace/patio

Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington
4.0 star property
Burlington
9.8 out of 10, Exceptional, (1,002 reviews)
"Peaceful, clean, beautiful.friendly staffing Sure will go back "
United States
Marie
Archer Hotel Boston/Burlington
Courtyard

Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston
3.0 star property
Andover
9.0 out of 10, Wonderful, (1,010 reviews)
"Great staff and very good rooms. Great breakfast. "
United States
Albert
The price is ฿3,243
฿3,623 total
includes taxes & fees
8 Mar - 9 Mar
Sonesta ES Suites Andover Boston
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, (1,006 reviews)
"Wonderful stay "
United States
Fernando
The price is ฿2,768
฿4,128 total
includes taxes & fees
1 Mar - 2 Mar
Staypineapple, A Delightful Hotel, South End
Reception

Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree
3.5 star property
North Braintree
9.0 out of 10, Wonderful, (2,701 reviews)
"Clean room great breakfast, and super front desk staff"
United States
Mark
The price is ฿3,250
฿3,631 total
includes taxes & fees
8 Mar - 9 Mar
Hyatt Place Boston/Braintree
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, (1,002 reviews)
"The room was nice and clean and the staff were great. "
United States
Kristy
The price is ฿2,719
฿3,038 total
includes taxes & fees
26 Feb - 27 Feb
Hilton Garden Inn Boston/Waltham
Property entrance

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
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, (2,011 reviews)
"Perfect stay. "
United States
Alyssa
The price is ฿3,087
฿3,449 total
includes taxes & fees
5 Mar - 6 Mar
La Quinta Inn & Suites by Wyndham Boston-Andover
BBQ/picnic Area

HYATT house Boston/Waltham

HYATT house Boston/Waltham
3.0 star property
Waltham
8.8 out of 10, Excellent, (1,099 reviews)
"Super clean and quiet, friendly staff, convenient location"
United States
Taylor
The price is ฿3,328
฿3,718 total
includes taxes & fees
27 Feb - 28 Feb
HYATT house Boston/Waltham
Lobby

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
3.0 star property
Spring Hill
9.6 out of 10, Exceptional, (1,008 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 ฿4,454
฿4,975 total
includes taxes & fees
15 Mar - 16 Mar
Cambria Hotel Boston Somerville
Reception

Hotel 1868

Hotel 1868
3.5 star property
Agassiz
9.6 out of 10, Exceptional, (1,002 reviews)
"Loved the room and the service! "
United States
Tracie
The price is ฿3,891
฿4,512 total
includes taxes & fees
23 Feb - 24 Feb
Hotel 1868
Lobby

Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham
3.0 star property
Waltham
9.4 out of 10, Exceptional, (1,648 reviews)
"The room, facilities and staff were great."
United States
Michael
The price is ฿2,787
฿3,113 total
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn & Suites Boston/Waltham
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 Dagny Boston

The Dagny Boston

10/10 Excellent
"The service was phenomenal. I’ve stayed at so many hotels/resorts this hotels service stood out to me. They went above & beyond to make us feel welcome & comfortable. The property location was perfect for walking downtown. The cafe wasn’t great despite the good reviews but everything else was 5/5 stars for me & my family. "
Jada 3-night trip
Posted 14 hours ago
The Dagny Boston

More cheap stays in Winchester

Ramada by Wyndham Boston

Ramada by Wyndham Boston

800 Morrissey Blvd Boston MA
The price is ฿2,408 per night from 22 Feb to 23 Feb
฿2,408
฿2,804 total
22 Feb - 23 Feb
includes taxes & fees
6.8/10 (1,624 reviews)

Hotels in Winchester with star rating

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 The Revolution Hotel and The Langham, Boston. 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?
The Langham, Boston: Hotel, 4-minute walk from Boston Harbor. Provides a sauna, an indoor pool and complimentary high-speed (wired) Internet access. Omni Boston Hotel at the Seaport and Seaport Hotel 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. Fenway Park, Encore Boston Harbor 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 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.