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 from CA $221

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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

Smart TV, fireplace
Dining
Interior
1 bedroom, in-room safe, iron/ironing board, WiFi

1. The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
United States
L M C.
CA $132
CA $240 total
includes taxes & fees
Sep 27 - Sep 28
The Pistachio Room at TPH - Boston
Interior
Coffee/tea maker, fridge, microwave, oven
5 bedrooms, iron/ironing board, travel crib, WiFi (free)
Interior

2. 5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
Melrose
United States
KATIE G.
CA $346
CA $790 total
includes taxes & fees
Sep 27 - Sep 28
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
Lobby
Ballroom
2 bars/lounges
Lobby

3. Hilton Boston Park Plaza

Hilton Boston Park Plaza
Bay Village
United States
Gabrielle
CA $348
CA $463 total
includes taxes & fees
Sep 20 - Sep 21
Hilton Boston Park Plaza
Interior
Exterior
2 bedrooms, iron/ironing board, WiFi, bed sheets
Terrace/patio

4. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
United States
Jenn K.
CA $285
CA $391 total
includes taxes & fees
Sep 20 - Sep 21
Near Boston Historic two-bedroom with Modern Amenities
1 bedroom, desk, iron/ironing board, WiFi (free)
Exterior
Smart TV
Interior

5. Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston

Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
Watertown
United States
Melissa F.
CA $208
CA $353 total
includes taxes & fees
Oct 13 - Oct 14
Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
Breakfast, lunch, dinner and brunch served
Interior detail
Bicycling
Exterior

6. The Dagny Boston

The Dagny Boston
Downtown Boston
United States
Keith
CA $477
CA $605 total
includes taxes & fees
Sep 20 - Sep 21
The Dagny Boston
2 bars/lounges
2 bars/lounges
Garden
2 bars/lounges

7. Concord's Colonial Inn

Concord's Colonial Inn
Concord
United States
Michelle
CA $198
CA $221 total
includes taxes & fees
Sep 28 - Sep 29
Concord's Colonial Inn
Exterior detail
Coffee/tea maker, fridge, microwave, oven
Interior
Terrace/patio

8. The heart Cambridge/Boston Studio private yard free permit parking 1#

The heart Cambridge/Boston Studio private yard free permit parking 1#
Cambridgeport
United States
Karen B.
CA $225
CA $442 total
includes taxes & fees
Sep 30 - Oct 1
The heart Cambridge/Boston Studio private yard free permit parking 1#
Exterior detail
1 bedroom, in-room safe, iron/ironing board, WiFi (free)
Dining
Coffee/tea maker, fridge, microwave, oven

9. Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#

Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
Cambridgeport
United States
Anonymous traveller
CA $238
CA $447 total
includes taxes & fees
Sep 20 - Sep 21
Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
Exterior
Lobby
Free daily buffet breakfast
Lobby

10. The Kendall Hotel at the Engine 7 Firehouse

The Kendall Hotel at the Engine 7 Firehouse
MIT
United States
Brenda
CA $385
CA $493 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 8 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 8 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 8 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 10 hours ago
Omni Parker House
Hilton Boston Park Plaza

Hilton Boston Park Plaza

10/10 Excellent
"Clean rooms, friendly staff, & great service"
Gabrielle 2-night trip
Posted 14 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 20 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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