Winchester Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Winchester hotels

La Quinta Inn & Suites by Wyndham Boston-Andover

3.0 star property
8.2 out of 10, Very Good, (1817)
"Cimfortable bed, good shower, clean."
The price is P6,891
P7,698 total
includes taxes & fees
Aug 14 - Aug 15
La Quinta Inn & Suites by Wyndham Boston-Andover

The Beverly

3.0 star property
8.4 out of 10, Very Good, (326)
"Soft sheets, easy check-in and check-out, and lots of space. Great value."
The price is P8,847
P9,882 total
includes taxes & fees
Aug 3 - Aug 4
The Beverly

Sonesta Select Boston Danvers

3.0 star property
8.6 out of 10, Excellent, (1002)
"Great place"
The price is P7,381
P8,245 total
includes taxes & fees
Sep 2 - Sep 3
Sonesta Select Boston Danvers

The Wylie Inn and Conference Center at Endicott College

3.5 star property
9.0 out of 10, Wonderful, (1063)
"Gorgeous location and wonderful hotel. "
The price is P8,009
P8,946 total
includes taxes & fees
Aug 6 - Aug 7
The Wylie Inn and Conference Center at Endicott College

Best Western Plus North Shore Hotel

2.5 star property
9.0 out of 10, Wonderful, (1004)
"Nice to stay"
The price is P9,474
P10,583 total
includes taxes & fees
Aug 10 - Aug 11
Best Western Plus North Shore Hotel

The Boxboro Regency

3.0 star property
7.2 out of 10, Good, (1005)
"Dated and charming property. Great stay!"
The Boxboro Regency

Sonesta ES Suites Andover Boston

2.5 star property
8.8 out of 10, Excellent, (1004)
"Excellent stay. "
The price is P7,193
P8,035 total
includes taxes & fees
Sep 1 - Sep 2
Sonesta ES Suites Andover Boston

Nantasket Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1004)
"Nice location, wonderful staff"
The price is P8,677
P10,878 total
includes taxes & fees
Sep 1 - Sep 2
Nantasket Beach Resort

Bedford Plaza Hotel - Boston

2.5 star property
7.4 out of 10, Good, (379)
"Would definitely stay again !"
The price is P6,125
P6,841 total
includes taxes & fees
Aug 3 - Aug 4
Bedford Plaza Hotel - Boston

Nantasket Beach Hotel

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Nice room across the street from the beach and within walking distance to some decent restaurants. "
Nantasket Beach Hotel

The Cove At Salem

3.0 star property
9.4 out of 10, Exceptional, (641)
"It was a wonderful stay."
The price is P10,417
P11,636 total
includes taxes & fees
Aug 6 - Aug 7
The Cove At Salem

The Hotel Salem

3.0 star property
9.2 out of 10, Wonderful, (1012)
"This place is amazing! Comfy beds, spacious rooms, friendly staff and close to everything! Will recommend and stay again"
The price is P10,996
P12,282 total
includes taxes & fees
Aug 5 - Aug 6
The Hotel Salem

Hawthorne Hotel

3.5 star property
9.4 out of 10, Exceptional, (1312)
"The hotel and our room were beautiful. Fantastic place to stay. "
Hawthorne Hotel

Hilton Garden Inn Tewksbury Andover

3.0 star property
8.8 out of 10, Excellent, (695)
"Just love being at this Hilton!!!"
The price is P6,863
P7,666 total
includes taxes & fees
Aug 10 - Aug 11
Hilton Garden Inn Tewksbury Andover

Andover Inn

3.5 star property
9.2 out of 10, Wonderful, (439)
"Great location."
The price is P8,650
P9,662 total
includes taxes & fees
Aug 3 - Aug 4
Andover Inn

HYATT house Boston/Waltham

3.0 star property
8.8 out of 10, Excellent, (1003)
"Great place!"
The price is P7,271
P8,121 total
includes taxes & fees
Sep 1 - Sep 2
HYATT house Boston/Waltham

Best Western Plus Waltham Boston

3.0 star property
8.0 out of 10, Very Good, (1005)
"Clean place, great restaurant. "
The price is P5,769
P6,444 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Waltham Boston

Aloft by Marriott, Boston Seaport District

3.0 star property
9.0 out of 10, Wonderful, (1330)
"Loved our stay "
The price is P9,015
P12,192 total
includes taxes & fees
Aug 24 - Aug 25
Aloft by Marriott, Boston Seaport District

Omni Boston Hotel at the Seaport

4.0 star property
9.2 out of 10, Wonderful, (3759)
"Great stay !"
The price is P10,656
P14,779 total
includes taxes & fees
Aug 24 - Aug 25
Omni Boston Hotel at the Seaport

Archer Hotel Boston/Burlington

4.0 star property
9.6 out of 10, Exceptional, (1002)
"Good place to stay "
Archer Hotel Boston/Burlington
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.
Save an average of 15% on thousands of hotels when you're signed in

Near an Attraction

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 citizenM Boston Back Bay and citizenM Boston North Station. 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! 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.