A coastal town with a lighthouse, sandy beach, and residential buildings.

Find Historic Hotels in Winthrop, MA from CA $243

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Check availability on Winthrop Historic Hotels

Tonight
Sep 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Winthrop historic hotels

Little Pearl
Butter soft sofa provides additional sleep space for one.
Interior
cable tv and wifi

1. Your Floating Suite in Boston Harbor

Your Floating Suite in Boston Harbor
Thompson Square - Bunker Hill
United States
Jason J.
CA $184
CA $728 total
includes taxes & fees
Sep 29 - Sep 30
Your Floating Suite in Boston Harbor
A restaurant with a long dining area, high ceilings, and exposed beams. Tables are set with glassware and centerpieces.
A grand lobby with a large arched entrance, a high ceiling with a detailed mural, and a view of the street outside.
A couple walking on a sidewalk with a restaurant named "THE DAGNY" in the background.
A building with a sign reading "THE DAGNY" and a brick facade. There are two bicycles parked in front.

2. The Dagny Boston

The Dagny Boston
Downtown Boston
United States
Carol
CA $480
CA $609 total
includes taxes & fees
Oct 29 - Oct 30
The Dagny Boston
Lobby
Lobby
Room
Bar (on property)

3. The Kendall Hotel at the Engine 7 Firehouse

The Kendall Hotel at the Engine 7 Firehouse
MIT
United States
Fiona
CA $386
CA $495 total
includes taxes & fees
Oct 11 - Oct 12
The Kendall Hotel at the Engine 7 Firehouse
A living room with a brick fireplace, a brown leather sofa, a patterned rug, and a dining area with a table and chairs.
A room with a wooden floor, a large window with curtains, a chandelier, and a potted plant with white flowers.
A living room with a brown leather sofa, two patterned throw pillows, a small wooden side table with a stack of books, and a window with white curtains.
A bedroom with a bed, bedside lamps, a window with curtains, a painting on the wall, and a hallway leading to another room.

4. The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
United States
L M C.
CA $134
CA $243 total
includes taxes & fees
Oct 4 - Oct 5
The Pistachio Room at TPH - Boston
A spacious lobby with a central seating area, a bar, and a chandelier.
A hotel with a classic facade, large windows, and an American flag.
A spacious lobby with a modern design, featuring a sofa, armchairs, a dining area, and a large staircase.
A spacious lobby with a grand chandelier, a reception desk, and a seating area with a table and chairs.

5. Hilton Boston Park Plaza

Hilton Boston Park Plaza
Bay Village
United States
Lesley
CA $386
CA $508 total
includes taxes & fees
Oct 4 - Oct 5
Hilton Boston Park Plaza
A marina with boats docked, a red brick building, and modern high-rise apartments in the background.
A dining area with a wooden table and white chairs, a window with a view of a waterfront and buildings, and a wooden ceiling with exposed beams.
A kitchen with a bar area, wooden paneling, and a view of a dock.
A wooden dock extending into calm water with a sunset in the background.

6. Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
United States
Angela L.
CA $290
CA $858 total
includes taxes & fees
Oct 27 - Oct 28
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A spacious living room with a dining area, wooden columns, and a large window providing natural light.
A dining area with a wooden table, chairs, a potted plant, and a fireplace.
A two-story house with a covered patio, a staircase, and a garden area.
A two-story house with a front porch, a staircase, and a driveway.

7. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
United States
Jenn K.
CA $283
CA $410 total
includes taxes & fees
Sep 30 - Oct 1
Near Boston Historic two-bedroom with Modern Amenities
An outdoor patio area with a covered seating area, a fire pit, and a well-lit ambiance.
A kitchen with white cabinets, a backsplash, and a brick wall. There is a sign that reads "BOSTON CITY LIMITS."
A spacious hotel room with a large bed, a television, and a brick wall.
A modern kitchen with white cabinetry, a red kettle, and a variety of kitchen items on the counter.

8. 🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
United States
Katie C.
CA $141
CA $465 total
includes taxes & fees
Oct 18 - Oct 19
🎖The Boiler Room - Close to Subway & Downtown🎖
An outdoor patio area with a covered seating area, a fire pit, and a well-lit ambiance.
A spacious living room with a large flat-screen TV mounted on the wall, a wooden coffee table, and a comfortable sofa.
A modern living room with a flat-screen TV, a sofa, a coffee table, and a bed with a headboard.
A modern kitchen with white cabinetry, stainless steel appliances, and pendant lighting.

9. 🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Dorchester
United States
Elizabeth F.
CA $281
CA $642 total
includes taxes & fees
Sep 30 - Oct 1
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
A spacious living area with a large sectional sofa, a glass dining table, and multiple windows providing natural light.
A green bridge spanning a river with a marina and residential buildings in the foreground.
A brick building with a covered patio, outdoor seating, and a well-maintained garden.
A large brick building with a central entrance, steps leading up to it, and a well-maintained lawn.

10. Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Chelsea
United States
Ted W.
CA $509
CA $962 total
includes taxes & fees
Oct 4 - Oct 5
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
View all properties

Top Winthrop Hotel Reviews

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

8/10 Good
"Clean, not really a breakfast though, more like a snack."
Julie 4-night trip
Posted less than an hour ago
The Midtown Hotel MOD Collection by Sonesta
Harborside Inn Of Boston

Harborside Inn Of Boston

8/10 Good
"Clean and very convenient location to everything!"
Glenn 1-night trip
Posted less than an hour ago
Harborside Inn Of Boston
The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"This was a wonderful hotel in a great location. Just a few steps away from the freedom trail. The hotel is very upscale. Has a great coffee shop in the bottom and a really good restaurant-Ruka- which I did a DoorDash order from. Free water and snacks in the room and they had a clothes steamer in the wardrobe! The staff were very attentive, friendly, and accommodating. The front lobby is a great place to hang out as well."
Holly 1-night trip
Posted 2 hours ago
The Godfrey Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

8/10 Good
"Beautiful hotel located in great location near all sites. Only complaint is that the air conditioning unit was quite noisy. This would not prevent us from staying here again,"
Ines 2-night trip
Posted 2 hours ago
Hilton Boston Park Plaza
Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

10/10 Excellent
"Great location"
Brent 5-night trip
Posted 3 hours ago
Copley Square Hotel, a FOUND Hotel

Frequently asked questions

What should a history buff expect from a stay in Winthrop?
A trip to the historical places in Winthrop is probably on top of your sightseeing list. While you're here, why not check out the beaches and restaurants?
How many historical hotels will I find in Winthrop?
Winthrop is home to 18 hotel accommodations bookable on Expedia but not many designated as historic hotels.
What are the must-see historical places and other sights in Winthrop?
Favorite places to visit include Winthrop Beach, Winthrop Shore Reservation, and Donovan Beach. In the area, you'll also find Fenway Park and Boston Harbor.
What is a historic hotel like in Winthrop?
By choosing a historic hotel, you can spend a night or two in a place that has a national historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be turned into a historic hotel provided that it's of special interest. Traditional architecture and period features are typically preserved within the guestrooms or public spaces of historic hotels in Winthrop, giving a sense of history.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is more common in the U.S. though overall the terms are quite similar. The architecture and building of a historic hotel is generally the most important aspect. For a heritage hotel, often it's the cultural value as well as how it influenced the community.
Do historic hotels in Winthrop have modern facilities?
Hotels have the safety features and modern conveniences you've come to expect, but every effort is made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the amenities found in a hotel should be available at a historic hotel. When you choose a historic hotel in Winthrop, don't worry that you'll find a place that's uncomfortable or rundown.

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