Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.

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Check prices for these dates

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Jun 12 - Jun 14
Next weekend
Jun 19 - Jun 21

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Our top choices for Winchester hotels

View from property

Nantasket Beach Resort

Nantasket Beach Resort
3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1,013 reviews)
"Very cute, great vacation spot"
United States
sharon
The price is ￥29,495
￥36,891 total
includes taxes & fees
Jun 14 - Jun 15
Nantasket Beach Resort
Front of property

The Hotel Marblehead

The Hotel Marblehead
3.5 star property
Marblehead
9.2 out of 10, Wonderful, (505 reviews)
"Clean room and comfortable beds!"
United States
Adam
The price is ￥30,094
￥33,614 total
includes taxes & fees
Jul 6 - Jul 7
The Hotel Marblehead
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, (1,176 reviews)
"Top notch place to stay, and the ability to walk to the shore was delightful."
United States
Dirk
The price is ￥28,553
￥31,894 total
includes taxes & fees
Jun 15 - Jun 16
The Wylie Inn and Conference Center at Endicott College
Bar (on property)

Hawthorne Hotel

Hawthorne Hotel
3.5 star property
Downtown Salem
9.4 out of 10, Exceptional, (1,590 reviews)
"Great hotel! Was in perfect location in Salem!! We had a wonderful stay there on our girls trip!!"
United States
Samantha Lynn
The price is ￥39,592
￥44,225 total
includes taxes & fees
Jun 21 - Jun 22
Hawthorne Hotel
Porch

The Cove At Salem

The Cove At Salem
3.0 star property
Salem
9.4 out of 10, Exceptional, (995 reviews)
"The place was great, the room was awesome. The location is perfect, I would have liked to use the patio but it was unfortunately raining."
United States
Ryan
The price is ￥33,552
￥37,478 total
includes taxes & fees
Jun 30 - Jul 1
The Cove At Salem
Lobby

The Hotel Salem

The Hotel Salem
3.0 star property
Downtown Salem
9.4 out of 10, Exceptional, (1,017 reviews)
"Amazing location and good service."
United States
Chris
The price is ￥35,653
￥39,824 total
includes taxes & fees
Jul 5 - Jul 6
The Hotel Salem
Reception

Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree
3.5 star property
North Braintree
9.0 out of 10, Wonderful, (2,866 reviews)
"Great Stay."
United States
Mark
The price is ￥25,166
￥28,111 total
includes taxes & fees
Jun 30 - Jul 1
Hyatt Place Boston/Braintree
Exterior

Best Western Braintree Inn

Best Western Braintree Inn
2.5 star property
North Braintree
8.2 out of 10, Very Good, (1,009 reviews)
"Parking was safe and easy, Room was clean. Friendly staff"
United States
Mary-Beth
The price is ￥20,422
￥22,812 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Braintree Inn
Restaurant

Sonesta Select Boston Danvers

Sonesta Select Boston Danvers
3.0 star property
Danvers
8.6 out of 10, Excellent, (1,015 reviews)
"Great stay"
United States
Verinda
The price is ￥27,286
￥30,479 total
includes taxes & fees
Jul 1 - Jul 2
Sonesta Select Boston Danvers
Lobby

Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport
2.5 star property
Revere
9.0 out of 10, Wonderful, (2,325 reviews)
"The cleanliness was awesome, breakfast was great and staff were top notch..."
United States
Frank
The price is ￥27,554
￥31,741 total
includes taxes & fees
Jul 2 - Jul 3
Comfort Inn & Suites Logan International Airport
Dinner served

Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport
3.0 star property
Revere
8.2 out of 10, Very Good, (5,628 reviews)
"Amazing breakfast, kind staff and very clean rooms!"
United States
Breanna
The price is ￥21,848
￥24,404 total
includes taxes & fees
Jul 2 - Jul 3
Hampton Inn Boston - Logan Airport
Exterior

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, (1,601 reviews)
"Very clean, comfortable and convenient to stay night before early morning flight."
United States
Douglas
The price is ￥25,367
￥28,335 total
includes taxes & fees
Jul 2 - Jul 3
avid hotel Boston Logan Airport - Revere by IHG
Exterior

Hilton Garden Inn Boston Logan Airport

Hilton Garden Inn Boston Logan Airport
3.0 star property
East Boston
9.2 out of 10, Wonderful, (2,301 reviews)
"Great stay!"
United States
Rachel
The price is ￥26,624
￥31,005 total
includes taxes & fees
Jul 6 - Jul 7
Hilton Garden Inn Boston Logan Airport
Lobby

Hilton Boston Logan Airport

Hilton Boston Logan Airport
4.0 star property
East Boston
9.0 out of 10, Wonderful, (3,828 reviews)
"Great place to stay "
United States
William
The price is ￥36,031
￥41,958 total
includes taxes & fees
Jul 5 - Jul 6
Hilton Boston Logan Airport
Sports facility

Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor
4.0 star property
East Boston
9.2 out of 10, Wonderful, (1,904 reviews)
"It's a great place to stay"
United States
James
The price is ￥36,233
￥46,203 total
includes taxes & fees
Jul 1 - Jul 2
Hyatt Regency Boston Harbor
Lobby

Homewood Suites by Hilton Boston Seaport District

Homewood Suites by Hilton Boston Seaport District
3.0 star property
Seaport District
9.2 out of 10, Wonderful, (1,497 reviews)
"Great location!"
United States
Alaina
The price is ￥28,803
￥33,109 total
includes taxes & fees
Jul 5 - Jul 6
Homewood Suites by Hilton Boston Seaport District
Exterior

Hampton by Hilton at the Boston Seaport District

Hampton by Hilton at the Boston Seaport District
3.0 star property
Seaport District
9.2 out of 10, Wonderful, (2,884 reviews)
"Great for just an overnight.. clean room and friendly staff."
United States
Barbara
The price is ￥28,711
￥33,433 total
includes taxes & fees
Jul 5 - Jul 6
Hampton by Hilton at the Boston Seaport District
Marina

Best Western Adams Inn Quincy-Boston

Best Western Adams Inn Quincy-Boston
2.5 star property
Quincy
7.6 out of 10, Good, (1,171 reviews)
"Staff were incredibly friendly and helpful throughout our stay."
United States
Riley
The price is ￥24,275
￥27,115 total
includes taxes & fees
Jul 12 - Jul 13
Best Western Adams Inn Quincy-Boston
Bar (on property)

Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District
3.0 star property
Seaport District
9.4 out of 10, Exceptional, (2,403 reviews)
"Amazing place to stay!"
United States
Heather
The price is ￥40,803
￥47,515 total
includes taxes & fees
Jun 30 - Jul 1
Hyatt Place Boston/Seaport District
Executive Double Room | Individually decorated, individually furnished, blackout drapes

The Northshore Hotel - Boston/Danvers

The Northshore Hotel - Boston/Danvers
2.0 star property
Danvers
7.6 out of 10, Good, (1,025 reviews)
"Nice hotel… hard to find, but nice & quiet area…"
United States
Pamela
The price is ￥20,711
￥23,134 total
includes taxes & fees
Jun 14 - Jun 15
The Northshore Hotel - Boston/Danvers
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

4.5/5 (2 reviews)
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

Seaport Hotel Boston

Seaport Hotel Boston

8/10 Good
"This was a decent hotel overall. The best part is the location to restaurants and boardwalk. It was in South Boston the calmer side of Boston as North Boston is where all the action is with tourists. I feel the amenities could have been better considering you are charged a daily resort fee. The pool was a basic lap pool with no jacuzzi. The exercise area was small. We did enjoy the complimentary bikes which are helpful in getting around. The rooms were standard and no one cleaned our room for two days and I had to request it be cleaned. Staff were quick to address issues quickly as I had a few regarding service and beds. Food in restaurants were good. Overall this hotel was average and too pricey for what you get."
London 4-night trip
Posted 8 hours ago
Seaport Hotel Boston

More cheap stays in Winchester

Lakeside Inn

Lakeside Inn

595 North Ave Wakefield MA
The price is ￥14,115 per night from Jun 15 to Jun 16
￥14,115
￥15,766 total
Jun 15 - Jun 16
includes taxes & fees
7.6/10 Good! (2,371 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 The Revolution Hotel and Seaport Hotel Boston. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals that Winchester has to offer?
Cozy 3BD 1BA near Beach T-10 Min from Boston: This vacation home rental outside of Winchester is equipped with a patio, free WiFi, and a Smart TV to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. 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?
Omni Boston Hotel at the Seaport: Hotel, 2-minute walk from Boston Convention and Exhibition Center. Features 4 restaurants, an outdoor pool, and a full-service spa. 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. 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 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 Fenway Park and Encore Boston Harbor 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.

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