A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Find Historic Hotels in Winchester, MA

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Check availability on Winchester Historic Hotels

Tonight
Sep 18 - Sep 19
Tomorrow
Sep 19 - Sep 20
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Winchester historic hotels

Lobby
Exterior
Ballroom
2 bars/lounges

1. Hilton Boston Park Plaza

Hilton Boston Park Plaza
Bay Village
United States
Gabrielle
NT$7,306
NT$9,808 total
includes taxes & fees
Sep 20 - Sep 21
Hilton Boston Park Plaza
Breakfast, lunch, dinner and brunch served
Interior detail
Bicycling
Library

2. The Dagny Boston

The Dagny Boston
Downtown Boston
United States
Keith
NT$10,950
NT$13,865 total
includes taxes & fees
Sep 19 - Sep 20
The Dagny Boston
2 bars/lounges
2 bars/lounges
Garden
2 bars/lounges

3. Concord's Colonial Inn

Concord's Colonial Inn
Concord
United States
Michelle
NT$4,509
NT$5,036 total
includes taxes & fees
Sep 27 - Sep 28
Concord's Colonial Inn
Exterior
Lobby
Lobby
Free daily buffet breakfast

4. The Kendall Hotel at the Engine 7 Firehouse

The Kendall Hotel at the Engine 7 Firehouse
MIT
United States
Brenda
NT$8,773
NT$11,245 total
includes taxes & fees
Sep 20 - Sep 21
The Kendall Hotel at the Engine 7 Firehouse
View all properties

Top Winchester Hotel Reviews

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Great location by the water"
Mark 2-night trip
Posted 3 hours ago
Seaport Hotel Boston
Harborside Inn Of Boston

Harborside Inn Of Boston

8/10 Good
"Great location. Clean and helpful staff but no laundry facilities or gym. The restaurant next door has a great western omelette."
David 2-night trip
Posted 4 hours ago
Harborside Inn Of Boston
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

8/10 Good
"Need more coffee in the room. We stay 2 nights but no coffee replenishment.. house keeping was every 2 nights but but seems like need more coffee.."
Ratna 2-night trip
Posted 4 hours ago
Hilton Garden Inn Tewksbury Andover
Omni Parker House

Omni Parker House

10/10 Excellent
"Excellent stay with amazing staff"
Emily 3-night trip
Posted 6 hours ago
Omni Parker House
The Dagny Boston

The Dagny Boston

10/10 Excellent
"It was a fantastic stay- would absolutely recommend for any trip to boston!"
Kelsey 3-night trip
Posted 7 hours ago
The Dagny Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

10/10 Excellent
"Clean rooms, friendly staff, & great service"
Gabrielle 2-night trip
Posted 10 hours ago
Hilton Boston Park Plaza
The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

8/10 Good
"Very helpful staff. Clean room. No breakfast. Very expensive parking, Very good location walking distance to most places."
jim 3-night trip
Posted 15 hours ago
The Westin Copley Place, Boston, a Marriott Hotel

Frequently asked questions

What can I expect on my historical trip to Winchester?
You're already probably planning a visit to historical sites while on vacation in Winchester. You can also enjoy all there is to see and do such as the soccer matches and lake views
How many historical hotels are there in Winchester?
In Winchester, there are 7 hotels and other accommodations bookable on Expedia but not many designated as historic hotels.
What are the must-see historical places and other sights to visit in Winchester?
Favorite places to visit include Winter Pond, Middlesex Fells Reservation, and Griffin Photography Museum. In the area, you'll also find Fenway Park and Encore Boston Harbor.
What is a historic hotel like in Winchester?
Guests who book a historic hotel can enjoy a vacation in a building that has a national historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be transformed into a historic hotel as long as it's of special interest. Traditional architecture and period features are typically found within the guestrooms or public spaces of historic hotels in Winchester, giving a sense of history.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. but overall the terms are quite similar. The architecture and actual building of a historic hotel is generally what's most important. For a heritage hotel, often it's the cultural value and how it inspired the community.
Do historic hotels in Winchester have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, though efforts have been made to preserve historic facades and treasured traditions. Smart TVs, WiFi, updated bathroom facilities, and the amenities found in any hotel should be available at a historic hotel. Rest assured that when you select a historic hotel in Winchester, you won't find yourself staying at a place that's uncomfortable for guests or simply rundown.

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