Find hotels in Winchester, MA from ¥16,665

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Compare 3,767 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Nantasket Beach Hotel

2.5 star property
9.2 out of 10, Wonderful, (1010)
"Always a great relaxing stay here!"
Nantasket Beach Hotel

Nantasket Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1007)
"We had a short overnight stay, super comfy beds, beautiful resort and very convenient location across street from the heach. "
The price is ¥20,719
¥26,182 total
includes taxes & fees
Sep 2 - Sep 3
Nantasket Beach Resort

The Wylie Inn and Conference Center at Endicott College

3.5 star property
9.0 out of 10, Wonderful, (1080)
"Gorgeous location and wonderful hotel. "
The price is ¥21,362
¥23,861 total
includes taxes & fees
Aug 17 - Aug 18
The Wylie Inn and Conference Center at Endicott College

Hawthorne Hotel

3.5 star property
9.4 out of 10, Exceptional, (1341)
"Amazing stay and I loved it will def be returning "
Hawthorne Hotel

The Cove At Salem

3.0 star property
9.4 out of 10, Exceptional, (656)
"It was a wonderful stay."
The price is ¥26,460
¥29,557 total
includes taxes & fees
Aug 20 - Aug 21
The Cove At Salem

The Hotel Salem

3.0 star property
9.2 out of 10, Wonderful, (1014)
"Great location and roof top deck"
The price is ¥33,651
¥37,587 total
includes taxes & fees
Aug 24 - Aug 25
The Hotel Salem

Howard Johnson by Wyndham Quincy/Boston

2.0 star property
7.8 out of 10, Good, (1004)
"I had an awsome stay will definitely go back again"
The price is ¥19,208
¥21,456 total
includes taxes & fees
Aug 24 - Aug 25
Howard Johnson by Wyndham Quincy/Boston

Hyatt Place Boston/Braintree

3.5 star property
9.0 out of 10, Wonderful, (2443)
"Great stay!"
The price is ¥19,509
¥21,791 total
includes taxes & fees
Sep 3 - Sep 4
Hyatt Place Boston/Braintree

Best Western Braintree Inn

2.5 star property
8.0 out of 10, Very Good, (1014)
"Great affordable hotel near Boston! I enjoyed my stay"
The price is ¥23,491
¥26,239 total
includes taxes & fees
Aug 13 - Aug 14
Best Western Braintree Inn

Sonesta Select Boston Danvers

3.0 star property
8.4 out of 10, Very Good, (1011)
"Great stay! "
The price is ¥19,148
¥21,388 total
includes taxes & fees
Sep 2 - Sep 3
Sonesta Select Boston Danvers

Best Western Adams Inn Quincy-Boston

2.5 star property
7.4 out of 10, Good, (1007)
"Hotel was really clean and nice. Excellent stay!!"
The price is ¥21,210
¥23,692 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Adams Inn Quincy-Boston

Hampton Inn Boston - Logan Airport

3.0 star property
8.2 out of 10, Very Good, (5209)
"Great place, great breakfast!"
The price is ¥22,976
¥25,663 total
includes taxes & fees
Aug 18 - Aug 19
Hampton Inn Boston - Logan Airport

Hyatt Regency Boston Harbor

4.0 star property
9.2 out of 10, Wonderful, (1567)
"Great Staff and Great View of the Boston Harbor!"
The price is ¥23,565
¥31,147 total
includes taxes & fees
Sep 1 - Sep 2
Hyatt Regency Boston Harbor

Hyatt Place Boston/Seaport District

3.0 star property
9.4 out of 10, Exceptional, (2095)
"Great stay "
The price is ¥31,513
¥36,696 total
includes taxes & fees
Aug 17 - Aug 18
Hyatt Place Boston/Seaport District

Embassy Suites Boston Logan Airport

3.5 star property
8.8 out of 10, Excellent, (2044)
"Excellent hotel located right at the airport!"
The price is ¥27,134
¥32,338 total
includes taxes & fees
Sep 1 - Sep 2
Embassy Suites Boston Logan Airport

Seaport Hotel Boston

4.0 star property
9.6 out of 10, Exceptional, (3211)
"We had a wonderful stay!"
The price is ¥27,122
¥32,323 total
includes taxes & fees
Aug 13 - Aug 14
Seaport Hotel Boston

Omni Boston Hotel at the Seaport

4.0 star property
9.2 out of 10, Wonderful, (3820)
"Great stay !"
The price is ¥30,184
¥41,190 total
includes taxes & fees
Aug 24 - Aug 25
Omni Boston Hotel at the Seaport

The Westin Boston Seaport District

4.0 star property
9.0 out of 10, Wonderful, (2092)
"Great stay!!"
The price is ¥26,544
¥36,088 total
includes taxes & fees
Aug 24 - Aug 25
The Westin Boston Seaport District

Aloft by Marriott, Boston Seaport District

3.0 star property
9.0 out of 10, Wonderful, (1327)
"Loved our stay "
The price is ¥22,973
¥31,065 total
includes taxes & fees
Aug 24 - Aug 25
Aloft by Marriott, Boston Seaport District

Best Western Plus North Shore Hotel

2.5 star property
9.0 out of 10, Wonderful, (1011)
"Nice to stay"
The price is ¥24,065
¥26,881 total
includes taxes & fees
Aug 19 - Aug 20
Best Western Plus North Shore Hotel
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Stay near popular Winchester attractions

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.

Top Winchester Hotel Reviews

Frequently asked questions

What's the best place to stay in Winchester?

Located 8.7 mi (14 km) from the heart of Winchester, Omni Boston Hotel at the Seaport is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Hilton Boston Park Plaza and citizenM Boston Back Bay. See all available top hotels, or vacation rentals in Winchester.

What are some of the best vacation rentals that Winchester has to offer?

House near down town Salem: This vacation home rental outside of Winchester offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. 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?

Embassy Suites Boston Logan Airport: 3.5-star hotel located near New England Aquarium. Features a snack bar, an indoor pool, and free buffet breakfast. Seaport Hotel 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 New England Aquarium are some of the top sights around the area. In Winchester, there are 3 hotels and other accommodations to choose from. Find out more about Winchester.

What are the top places to visit in Winchester?

The picturesque setting of Middlesex Fells Reservation and Winter Pond exemplify the area's natural beauty. 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.