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Find Historic Hotels in Middletown, NY

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Top Middletown Historic Hotels

Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1001)
"Parking was very easy, beautiful area, very nice staff"
United States
Elizabeth
$101 nightly
The price is $115
Nov 18 - Nov 19
Total with taxes and fees
Overlook Lodge at Bear Mountain
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (126)
"I cannot say enough on this location. Peaceful, and the view was extraordinary. Highly recommend this to anyone that wants a getaway."
United States
Daniel R.
$272 nightly
The price is $308
Nov 16 - Nov 17
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A heated pool
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #340

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #340

Vernon
10.0 out of 10, Exceptional, (18)
"Gerry’s place was very clean, well s"
United States
Kristina V.
$274 nightly
The price is $308
Nov 16 - Nov 17
Total with taxes and fees
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #340
Fridge, microwave, oven, stovetop
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Beacon
10.0 out of 10, Exceptional, (46)
"Great spot"
United States
Jim M.
$211 nightly
The price is $243
Nov 20 - Nov 21
Total with taxes and fees
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
A heated pool
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #342

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #342

Vernon
10.0 out of 10, Exceptional, (22)
"We love this place and we will definitely come back, a lot of activity’s around. And Mountain view is amazing."
United States
Mariana
$274 nightly
The price is $308
Nov 16 - Nov 17
Total with taxes and fees
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #342
A heated pool
Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #241

Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #241

Vernon
9.2 out of 10, Wonderful, (9)
"My wife and I had a great night peaceful 4 days really enjoyed this place"
United States
Roberto
$237 nightly
The price is $266
Nov 16 - Nov 17
Total with taxes and fees
Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #241
A heated pool
Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek sunsets

Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek sunsets

Vernon
9.4 out of 10, Exceptional, (26)
"Great location and rooms are very homey! The cafe on site was not stocked with food and was out of most items. "
United States
Joanna
$232 nightly
The price is $261
Dec 2 - Dec 3
Total with taxes and fees
Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek sunsets
A heated pool
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #246

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #246

Vernon
9.6 out of 10, Exceptional, (5)
"The condo was clean and exactly as the pictures show. The management company was efficient and check in was easy. I would definitely rent this condo again!"
United States
Alyson M.
$274 nightly
The price is $308
Nov 16 - Nov 17
Total with taxes and fees
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #246
A heated pool
Heated Pool Hot Tubs Sauna Gym Patio Mtn Front Appalachian @ Mtn Creek #136

Heated Pool Hot Tubs Sauna Gym Patio Mtn Front Appalachian @ Mtn Creek #136

Vernon
10.0 out of 10, Exceptional, (2)
"The room was nice, updated and clean. The location is so close to the ski lift you can literally Ski in and out of the room. The beds could be a little softer but are adequate. They are doing work in the hallways of the building but it didn't disturb us. The pool is also right outside the room. The hallways smelled like weed for our entire stay but it didn't get into our room and this is not the owners fault at all. The room was stocked with more then enough paper goods and soaps for our...
United States
Jeff B.
$414 nightly
The price is $466
Nov 16 - Nov 17
Total with taxes and fees
Heated Pool Hot Tubs Sauna Gym Patio Mtn Front Appalachian @ Mtn Creek #136
Outdoor pool, a heated pool
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

Vernon
9.8 out of 10, Exceptional, (87)
"Great experience"
United States
Pat M.
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf
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.
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Top Middletown Hotel Reviews

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"Everything was good "
Shontia 1-night trip
Posted 3 days ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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 43 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, in the area you'll find LEGOLAND® New York and Woodbury Common Premium Outlets.
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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