Find hotels in Winchester, MA from ฿2,869

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Our top choices for Winchester hotels

Terrace/patio
Hampton Inn Boston Woburn

Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.0 out of 10, Wonderful, (1358)
Slip into the indoor pool or work out at this Woburn hotel, just minutes from Burlington Mall and MarketStreet Lynnfield. Free breakfast, WiFi, parking, and a welcoming bar await after exploring Boston's attractions.
"Very good room and great breakfast!"
United States
Rodrigo
The price is ฿3,418
฿3,818 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Inn Boston Woburn
Lobby
Best Western Plus New Englander

Best Western Plus New Englander

Best Western Plus New Englander
2.5 star property
Woburn
8.6 out of 10, Excellent, (1000)
Just 15 minutes from Faneuil Hall and Harvard Square, this quiet Woburn hotel offers free breakfast, WiFi, and parking. Guests love the pool and helpful staff, with Burlington Mall nearby and a restaurant on-site for convenience.
"Clean room, decent location close to freeway, large & very popular restaurant attached to motel. Good option if you don't want to stay in Boston, so you can easily explore the area by car (free parking)"
United States
Kirsten
The price is ฿2,882
฿3,219 total
includes taxes & fees
29 Dec - 30 Dec
Best Western Plus New Englander
Lobby
Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
Watertown
9.4 out of 10, Exceptional, (1013)
Discover comfortable accommodation in Watertown, just a short drive from Harvard University and Fenway Park. This hotel provides a complimentary breakfast that guests love, fitness centre for workouts, and helpful staff to enhance your Boston-area visit.
"The room was very spacious and clean, the breakfast was very nice. "
United States
Kata Berta
The price is ฿3,290
฿3,675 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Watertown Boston
View from property
Sheraton Boston Needham Hotel

Sheraton Boston Needham Hotel

Sheraton Boston Needham Hotel
3.5 star property
Needham
8.8 out of 10, Excellent, (1526)
Quiet retreat with easy highway access, this hotel offers an indoor pool and on-site cafe with Starbucks. Just 15 minutes from Boston College and Northeastern University, guests praise the helpful staff and clean accommodation.
"Great experience amazing food"
United States
David
The price is ฿3,422
฿3,822 total
includes taxes & fees
30 Dec - 31 Dec
Sheraton Boston Needham Hotel
Terrace/patio
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover
3.0 star property
Tewksbury
8.8 out of 10, Excellent, (885)
"The staff is always courteous and the rooms are clean."
United States
Wilfredo
The price is ฿2,520
฿2,814 total
includes taxes & fees
31 Dec - 1 Jan 2026
Hilton Garden Inn Tewksbury Andover
Exterior
Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston
2.5 star property
Andover
9.0 out of 10, Wonderful, (1006)
Tucked in Andover, these comfortable suites offer a 24-hour fitness centre and outdoor swimming. Just 15 minutes from Canobie Lake Park with easy access to Methuen Memorial Music Hall. Guests love the helpful staff and pristine accommodation.
"The nicest hotel in the area. "
United States
Edna
The price is ฿3,455
฿3,859 total
includes taxes & fees
28 Dec - 29 Dec
Sonesta ES Suites Andover Boston
Free continental breakfast
La Quinta Inn & Suites by Wyndham Boston-Andover

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, (1953)
Minutes from Canobie Lake Park, this Andover hotel offers a tranquil base with free breakfast, WiFi, and parking. Enjoy the indoor pool year-round, workout at the fitness centre, and explore nearby Methuen Memorial Music Hall. Guests praise the helpful staff and quiet location.
"Enjoyed our stay"
United States
Christine
The price is ฿3,163
฿3,534 total
includes taxes & fees
29 Dec - 30 Dec
La Quinta Inn & Suites by Wyndham Boston-Andover
Exterior
Nantasket Beach Resort

Nantasket Beach Resort

Nantasket Beach Resort
3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1002)
"Staff was delightful and rooms were cute! "
United States
Robert
The price is ฿3,706
฿4,793 total
includes taxes & fees
28 Dec - 29 Dec
Nantasket Beach Resort
Exterior
Hyatt Place Boston/Medford

Hyatt Place Boston/Medford

Hyatt Place Boston/Medford
3.0 star property
Medford
8.4 out of 10, Very good, (1593)
Discover stylish comfort minutes from Boston's attractions. This Medford hotel offers 24-hour fitness facilities, fresh coffee around the clock, and convenient transport to Harvard Square and TD Garden. Guests praise the helpful staff and complimentary morning meal.
"Amazing stay and friendly staff! "
United States
Caterin
The price is ฿3,422
฿3,822 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hyatt Place Boston/Medford
Exterior
Hilton Garden Inn Boston Brookline, MA

Hilton Garden Inn Boston Brookline, MA

Hilton Garden Inn Boston Brookline, MA
3.0 star property
Brookline
9.0 out of 10, Wonderful, (1006)
Surrounded by Boston landmarks, this Brookline hotel offers an indoor pool, restaurant, and bar. Just 4 minutes from Brookline Village Station, enjoy easy access to Fenway Park and Children's Hospital Boston. Unwind in the 24-hour fitness centre after exploring the city.
"cleanliness, affordable, great location, great staff"
United States
Amy
The price is ฿4,056
฿4,530 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Boston Brookline, MA
Italian cuisine
Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
3.0 star property
Spring Hill
9.6 out of 10, Exceptional, (1008)
Experience Italian cuisine at Josephine restaurant after exploring nearby Harvard Square and TD Garden. A 24-hour gym keeps your routine on track, while helpful staff ensure a pleasant stay. Gilman Square Station is just 14 minutes away on foot.
"Great room, wonderful staff, convenient "
United States
Sarah
The price is ฿4,217
฿4,711 total
includes taxes & fees
2 Jan - 3 Jan 2026
Cambria Hotel Boston Somerville
Interior
The Arcadian Hotel

The Arcadian Hotel

The Arcadian Hotel
3.5 star property
Brookline
8.0 out of 10, Very good, (3862)
Step into this Brookline hotel with free continental breakfast and WiFi, just minutes from Fenway Park and top universities. Enjoy the 24-hour fitness centre, then explore nearby Harvard Square using Kent St. Station right outside.
"Wonderful stay"
United States
Victoria
The price is ฿2,889
฿4,270 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Arcadian Hotel
Indoor pool
Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG
2.5 star property
Chelmsford
8.8 out of 10, Excellent, (1000)
Discover comfort at this Chelmsford hotel with complimentary WiFi, parking, and hot breakfast. The indoor swimming pool offers relaxation after exploring nearby Bowlero Lowell or Cambodia Town. Business travellers appreciate the fitness centre and attentive service.
"Good stay"
United States
Jay
The price is ฿2,926
฿3,268 total
includes taxes & fees
30 Dec - 31 Dec
Holiday Inn Express Chelmsford by IHG
Daily full breakfast (USD 17 per person)
Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham

Hilton Garden Inn Boston/Waltham
3.0 star property
Waltham
8.8 out of 10, Excellent, (1001)
This tranquil Boston-area hotel offers an indoor pool and 24-hour fitness centre just 15 minutes from Harvard University. Enjoy American cuisine at The Garden Grille, plus clean rooms with refrigerators and microwaves near Moody Street Historic District.
"clean room, good location, great bathroom amenities, good staff"
United States
Sanjeev
The price is ฿2,526
฿2,821 total
includes taxes & fees
23 Jan - 24 Jan 2026
Hilton Garden Inn Boston/Waltham
Exterior
Lakeside Inn

Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
7.6 out of 10, Good, (2325)
This charming Wakefield hotel offers stunning lake views and peaceful surroundings. After enjoying a free breakfast, take a dip in the seasonal outdoor pool or unwind at Waves restaurant and bar. Just 15 minutes from Tufts University with complimentary parking.
"Another great stay!"
United States
Brian
Lakeside Inn
Exterior
Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG
3.0 star property
Saugus
8.6 out of 10, Excellent, (1001)
Surprisingly quiet Boston area retreat offering free breakfast, WiFi, and parking. The seasonal outdoor pool and 24-hour fitness centre enhance your stay. Located near shopping, restaurants, and just a short drive to city centre attractions.
"Nice hotel near everything "
United States
Patricia
The price is ฿2,706
฿3,023 total
includes taxes & fees
9 Jan - 10 Jan 2026
Holiday Inn Express Boston - Saugus by IHG
Exterior
La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville
3.0 star property
Assembly Square
7.6 out of 10, Good, (3063)
Stylish accommodation just minutes from Assembly Station with free WiFi, airport shuttle, and daily breakfast. Guests praise the comfortable beds and helpful staff, with TD Garden and Harvard Square nearby for exploration.
"Hotel looks old, but we had a very comfortable stay."
United States
Alejandro
The price is ฿2,380
฿2,658 total
includes taxes & fees
4 Jan - 5 Jan 2026
La Quinta Inn & Suites by Wyndham Boston Somerville
Indoor pool
Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham
2.5 star property
Waltham
9.4 out of 10, Exceptional, (1589)
Minutes from Harvard University, this welcoming hotel features an indoor pool and fitness centre. Guests praise the comfortable beds and helpful staff. Enjoy complimentary breakfast, WiFi, and parking, plus drinks at the bar. Lyman Estate and Walden Pond attractions are nearby.
"Clean room and friendly staff."
United States
Junghoon
The price is ฿2,780
฿3,106 total
includes taxes & fees
31 Dec - 1 Jan 2026
Hampton Inn & Suites Boston/Waltham
Reception
Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree
3.5 star property
North Braintree
9.0 out of 10, Wonderful, (2609)
Stay just 15 minutes from Northeastern University at this Braintree hotel offering free breakfast, WiFi, and parking. Enjoy American cuisine at 24/7 Gallery restaurant, workout in the fitness centre, or relax at the bar. Near South Shore Plaza with convenient transit options.
"Clean rooms, friendly staff, good breakfast and great location for visiting Boston."
United States
Chris
The price is ฿3,369
฿3,763 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hyatt Place Boston/Braintree
Reception
Hotel 1868

Hotel 1868

Hotel 1868
3.5 star property
Agassiz
9.4 out of 10, Exceptional, (1000)
Chic Cambridge hotel offers direct access to Porter Square Station for easy Harvard University visits. Contemporary rooms and a 24-hour fitness centre complement the excellent location near Harvard Square and Fenway Park with attentive staff to assist.
"Great stay overall "
United States
Elisabet
The price is ฿3,546
฿4,111 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hotel 1868
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

Hilton Boston Back Bay

Hilton Boston Back Bay

10/10 Excellent
"Clean room, convenient location."
Hua 3-night trip
Posted 2 days ago
Hilton Boston Back Bay

More cheap stays in Winchester

Ramada by Wyndham Boston

Ramada by Wyndham Boston

800 Morrissey Blvd Boston MA
The price is ฿2,464 per night from 31 Dec to 1 Jan
฿2,464
฿2,869 total
31 Dec - 1 Jan 2026
includes taxes & fees
6.6/10 (1,585 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 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.