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Check prices for these dates

Tonight
Jan 26 - Jan 27
Tomorrow
Jan 27 - Jan 28
This weekend
Jan 30 - Feb 1
Next weekend
Feb 6 - Feb 8

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Our top choices for Winchester hotels

Terrace/patio

Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
2.5 star property
Woburn
9.0 out of 10, Wonderful, (1,371 reviews)
"Very good room and great breakfast!"
United States
Rodrigo
The price is ￥17,236
￥19,253 total
includes taxes & fees
Feb 6 - Feb 7
Hampton Inn Boston Woburn
Exterior

Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
Watertown
9.4 out of 10, Exceptional, (1,019 reviews)
"Friendly staff, good free breakfast included!"
Canada
kennedy
The price is ￥17,314
￥19,340 total
includes taxes & fees
Feb 1 - Feb 2
Hampton Inn & Suites Watertown Boston
Lobby sitting area

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
3.0 star property
Chelsea
9.0 out of 10, Wonderful, (1,002 reviews)
"Room was clean and staff was very friendly and helpful. Will stay again. "
United States
Sonia
The price is ￥15,749
￥17,592 total
includes taxes & fees
Jan 28 - Jan 29
Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
Lobby

Hampton Inn Boston Bedford Burlington

Hampton Inn Boston Bedford Burlington
2.5 star property
Billerica
9.2 out of 10, Wonderful, (1,006 reviews)
"Staff very pleasant, clean room"
United States
Jean
The price is ￥15,193
￥16,971 total
includes taxes & fees
Feb 20 - Feb 21
Hampton Inn Boston Bedford Burlington
View from property

Nantasket Beach Resort

Nantasket Beach Resort
3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1,008 reviews)
"Great room off season, great view of the ocean. Have stayed before and will be back!"
United States
Patricia
The price is ￥18,552
￥24,363 total
includes taxes & fees
Jan 27 - Jan 28
Nantasket Beach Resort
Reception

Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree
3.5 star property
North Braintree
9.0 out of 10, Wonderful, (2,668 reviews)
"Staff was great, room was nice and clean!"
United States
Robert
The price is ￥17,602
￥19,661 total
includes taxes & fees
Feb 1 - Feb 2
Hyatt Place Boston/Braintree
Exterior

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, (1,049 reviews)
"Convenient to airport. "
United States
Patricia
The price is ￥13,702
￥15,305 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Express Boston - Saugus by IHG
Indoor pool

Sheraton Boston Needham Hotel

Sheraton Boston Needham Hotel
3.5 star property
Needham
8.8 out of 10, Excellent, (1,542 reviews)
"Great stay! Loved the location and staff was wonderful. Great gym. "
United States
Andrew
The price is ￥14,558
￥16,260 total
includes taxes & fees
Feb 1 - Feb 2
Sheraton Boston Needham Hotel
Courtyard

Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston
2.5 star property
Andover
8.8 out of 10, Excellent, (1,013 reviews)
"Staff is great and the hotel is clean "
United States
Fernando
The price is ￥16,193
￥18,087 total
includes taxes & fees
Feb 16 - Feb 17
Sonesta ES Suites Andover Boston
Lobby

Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea
4.0 star property
Chelsea
8.6 out of 10, Excellent, (1,680 reviews)
"Spotless room, friendly staff! "
United States
Crystal
The price is ￥15,193
￥16,971 total
includes taxes & fees
Jan 28 - Jan 29
Doubletree By Hilton Boston Logan Airport Chelsea
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, (1,990 reviews)
"Great stay ! "
United States
Gabby
The price is ￥15,274
￥17,061 total
includes taxes & fees
Feb 8 - Feb 9
La Quinta Inn & Suites by Wyndham Boston-Andover
Lobby sitting area

The Arcadian Hotel

The Arcadian Hotel
3.5 star property
Brookline
8.0 out of 10, Very Good, (3,898 reviews)
"Staff was courteous, hotel was in a good location "
United States
Jill
The price is ￥15,583
￥22,624 total
includes taxes & fees
Feb 1 - Feb 2
The Arcadian Hotel
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)
"I’ve stayed here numerous times. It’s my go to place when visiting the Boston area."
United States
Brian
The price is ￥12,640
￥14,120 total
includes taxes & fees
Jan 30 - Jan 31
Hilton Garden Inn Boston/Waltham
Lobby

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
3.0 star property
Spring Hill
9.6 out of 10, Exceptional, (1,005 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 ￥18,396
￥20,548 total
includes taxes & fees
Feb 1 - Feb 2
Cambria Hotel Boston Somerville
Porch

The Cove At Salem

The Cove At Salem
3.0 star property
Salem
9.4 out of 10, Exceptional, (882 reviews)
"Great place to stay "
United States
Krista
The price is ￥16,255
￥18,156 total
includes taxes & fees
Feb 1 - Feb 2
The Cove At Salem
Exterior

Hyatt Place Boston/Medford

Hyatt Place Boston/Medford
3.0 star property
Medford
8.4 out of 10, Very Good, (1,638 reviews)
"Great place!"
United States
EDILAINE
The price is ￥17,127
￥19,131 total
includes taxes & fees
Feb 1 - Feb 2
Hyatt Place Boston/Medford
Exterior

Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
7.6 out of 10, Good, (2,333 reviews)
"Another great stay!"
United States
Brian
Lakeside Inn
Free daily continental breakfast

avid hotel Boston Logan Airport - Revere by IHG

avid hotel Boston Logan Airport - Revere by IHG
2.5 star property
Revere
9.0 out of 10, Wonderful, (1,516 reviews)
"Clean rooms, convenient to airport and friendly staff. "
United States
Caitlin
The price is ￥16,193
￥18,087 total
includes taxes & fees
Jan 28 - Jan 29
avid hotel Boston Logan Airport - Revere by IHG
Lobby

Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham
2.5 star property
Waltham
9.4 out of 10, Exceptional, (1,623 reviews)
"Great hotel, very polite staff!"
United States
Cantay
The price is ￥11,376
￥12,706 total
includes taxes & fees
Feb 1 - Feb 2
Hampton Inn & Suites Boston/Waltham
Restaurant

Porter Square Hotel

Porter Square Hotel
3.0 star property
North Cambridge
9.2 out of 10, Wonderful, (1,003 reviews)
"This was a good place for a stay in a convenient location."
United States
Corey
The price is ￥17,747
￥20,578 total
includes taxes & fees
Feb 8 - Feb 9
Porter Square 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.
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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

The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Every single staff member I interacted with was very friendly and helpful. The entire hotel was lovely and clean, including my room. The on site restaurant, bar, and coffee spot were all great as well and overall contributed to an excellent experience. "
Hunter 2-night trip
Posted 8 hours 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 ￥11,376 per night from Feb 1 to Feb 2
￥11,376
￥12,706 total
Feb 1 - Feb 2
includes taxes & fees
9.2/10 Wonderful! (1,618 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
Located 8.6 mi (13.9 km) from the heart of Winchester, Seaport Hotel Boston is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Harborside Inn Of Boston and The Langham, Boston. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals that Winchester has to offer?
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino: This vacation home rental outside of Winchester is located on the waterfront and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! You'll find that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
To access more information about picking new dates or cancelling your trip to Winchester, head over to our customer service page.
What are some accommodations with pools in Winchester?
Seaport Hotel Boston: Hotel, 9-minute walk from Boston Convention and Exhibition Center. Features 2 restaurants, an indoor pool, and a health club. The Langham, Boston and Hilton Boston Logan Airport are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What's the best hotel for staying near Logan International Airport (BOS)?
Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.
What is staying in Winchester like?
Visitors can enjoy all that Winchester has to offer including the soccer matches and lake views. TD Garden, Fenway Park, and Encore Boston Harbor are some of the top sights around the area. In Winchester, there are 5 hotels and other accommodations to choose from. Find out more about Winchester.
What are the top places to visit in Winchester?
A couple of favorite places to visit are Winter Pond and Middlesex Fells Reservation. Additionally, you'll find TD Garden and Fenway Park in the area. Check out what more to see and do in Expedia's Winchester guide.
How should I get around Winchester?
To see more of 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 temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.