A lake surrounded by autumn-colored trees reflecting on the water.

Find Historic Hotels in Middletown, NY from CA $175

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Check availability on Middletown Historic Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Middletown historic hotels

A spacious dining area with multiple tables and chairs, a stone wall with a mounted deer head, and a fireplace.
A large outdoor swimming pool surrounded by trees and a covered pavilion.
A large, multi-story stone building with a prominent arched entrance and multiple windows.
A wooden reception desk with a man standing behind it, a staircase, and a wooden interior.

1. Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
Bear Mountain
United States
Lawrence
CA $148
CA $175 total
includes taxes & fees
Nov 2 - Nov 3
Overlook Lodge at Bear Mountain
A house with a view of a bridge and mountains.
A kitchen with a marble table, white chairs, wooden cabinets, a microwave, a toaster, and a clock on the wall.
A room with a telescope on a tripod near a window with a view of a mountainous landscape.
A room with a wooden dresser, a mirror, a red chair, and a patterned rug.

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
United States
Jasmine
CA $280
CA $474 total
includes taxes & fees
Oct 20 - Oct 21
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Interior
A large tree with white blossoms in front of a white building.
A well-maintained lawn, a garden with flowers, and a house with a porch.
A wooden-paneled bedroom with a bed, dresser, and a window with curtains.

3. Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets

Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets
Mountainville
United States
Robert D.
CA $1,626
CA $1,895 total
includes taxes & fees
Oct 18 - Oct 19
Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets
A stone pathway leading to a white gate, surrounded by lush greenery and a red building.
A wooden bench with a window above it, a pair of shoes on the floor, and a potted plant on the bench.
A modern kitchen with white cabinets, a black countertop, and a window with a view of greenery.
A cozy living room with a wood-burning stove, leather furniture, and a view of the outdoors.

4. Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.

Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.
Accord
United States
Stuart V.
CA $368
CA $757 total
includes taxes & fees
Nov 3 - Nov 4
Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.
View all properties

Top Middletown Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Bear Mountain Inn is a unique and beautiful retreat in the heart of the Hudson Valley. We go for the scenery, hiking, and watching the marine and rail traffic along the Hudson River. Staff is always helpful. We booked 2 nights but could only. stay 1 due to a family emergency and the staff worked with Expedia to refund the 2nd night. Will definitely return as we love the atmosphere. Stayed in 1 of the stone cottages in the woods above the lake. Basic room with a shared common area and outdoor porch/deck. Room had a small refrigerator and TV with local channels. Clean and quiet and what you'd expect in a state or national park setting. Great 1.5 mile paved walking trail below the cottage that circles the picturesque lake on the property grounds. Nice way to start the day."
Robert K 2-night trip
Posted 7 hours ago
Overlook Lodge at Bear Mountain
Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent
"Easy access from the highway. Friendly staff. Great value."
Bill 1-night trip
Posted 10 hours ago
Best Western Hunt's Landing Hotel Matamoras/Milford

Frequently asked questions

What should a history enthusiast expect from a trip to Middletown?
A trip to the historical sites in Middletown is probably first on your sightseeing list. During your stay, you can visit the shops and restaurants.
How many historical hotels are located in Middletown?
In Middletown, there are 63 hotels and other lodging options bookable on Expedia though not many historic hotels to choose from.
What are the most important historical sites and other places to visit in Middletown?
Middletown is notable for landmarks like Paramount Theatre. The picturesque setting of Highland Lake and Thomas Bull Memorial Park exemplify the area's natural beauty. Additionally, you'll find Woodbury Common Premium Outlets in the area.
What is a historic hotel like in Middletown?
Guests who choose a historic hotel can enjoy a vacation in a building that has an official historic designation. A castle, a palace or even a pub or an old police station can be transformed into a historic hotel as long as it's a place of special interest. Traditional architecture and period features are typically preserved in the public spaces and guestrooms of such hotels in Middletown, bringing the history to life.
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 a term often used in the U.S. but overall the terms are quite similar. The architecture and actual building of historic hotels tend to be the most significant aspect. For a heritage hotel, it's mainly the cultural value and how it shaped the community.
Do historic hotels in Middletown have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, but every effort is made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities, and the amenities found at a contemporary hotel will be available in a historic hotel. Rest assured that when you select a historic hotel in Middletown, you won't find yourself staying at a place that's uncomfortable or rundown.

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