Title: Book the Best HISTORIC Hotels in Middletown in 2025 | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d8864.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.ca/Middletown-Vacation-Rentals.d8864.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.ca/Cheap-Flights-To-Middletown.d8864.Travel-Guide-Flights)[Things to do in Middletown](https://expedia.ca/Things-To-Do-In-Middletown.d8864.Travel-Guide-Activities)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d8864.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.ca/Middletown.d8864.Destination-Travel-Guides) ![Route 17 in ny is a great road to view the fall foliage](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Vincent Ramundo # Find Historic Hotels in Middletown, NY from CA $165 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Middletown Historic Hotels Tonight [Nov 13 - Nov 14](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-11-13&endDate=2025-11-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 14 - Nov 15](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-11-14&endDate=2025-11-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middletown Historic Hotels ![Restaurant](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/383ffb6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Non Smoking (Stone Cottages at Bear Mountain)](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/42067525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain Bear Mountain 8.4/10 Very good (1002) "Parking was very easy, beautiful area, very nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $145 CA $165 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/67801e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands Fort Montgomery 9.8/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel R. CA $263 CA $431 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/40000000/39690000/39683500/39683459/46472573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/40000000/39690000/39683500/39683459/ea0c572d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/40000000/39690000/39683500/39683459/79184095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39690000/39683500/39683459/c3264217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #340 Vernon 10/10 Exceptional (18) "Gerry’s place was very clean, well s" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristina V. CA $209 CA $432 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Vernon-Hotels-Appalachian-Mtn-Creek-Pool-Hot-Tubs-Sauna-Gym-Deck-Mtn-Front-340.h39683459.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/ab271dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/13b54d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/04adf8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/97dee96b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer Beacon 10/10 Exceptional (46) "Great spot" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim M. CA $154 CA $341 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/40000000/39640000/39631300/39631236/dfd29c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/40000000/39640000/39631300/39631236/76cf78e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39640000/39631300/39631236/8904a079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/40000000/39640000/39631300/39631236/0685a0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #342 Vernon 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Mariana CA $209 CA $432 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Vernon-Hotels-Appalachian-Mtn-Creek-Pool-Hot-Tubs-Sauna-Gym-Deck-Mtn-Front-342.h39631236.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/75000000/74660000/74658300/74658223/fd568e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74660000/74658300/74658223/f72e512c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/75000000/74660000/74658300/74658223/fe281a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/75000000/74660000/74658300/74658223/79339c7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #241 Vernon 9.2/10 Wonderful (9) "My wife and I had a great night peaceful 4 days really enjoyed this place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberto CA $165 CA $373 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Vernon-Hotels-Heated-Pool-Hot-Tubs-Sauna-Gym-Mtn-Views-Appalachian-Mtn-Creek-241.h74658223.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/22000000/21710000/21700200/21700168/71f309f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/22000000/21710000/21700200/21700168/657b20fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/22000000/21710000/21700200/21700168/7cfab122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/22000000/21710000/21700200/21700168/6c1369f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek sunsets Vernon 9.4/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanna CA $171 CA $363 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Vernon-Hotels-Water-Park.h21700168.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/31000000/30360000/30358400/30358328/b81fb5b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/31000000/30360000/30358400/30358328/5f3802a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30360000/30358400/30358328/02984dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/31000000/30360000/30358400/30358328/d72ba3d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #246 Vernon 9.6/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyson M. CA $209 CA $432 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Vernon-Hotels-Cozy-1BR-The-Appalachian-Ski-InOut.h30358328.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/68000000/67350000/67340400/67340345/954dd944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/68000000/67350000/67340400/67340345/c03af65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/68000000/67350000/67340400/67340345/079fb1d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/68000000/67350000/67340400/67340345/8e308a69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool Hot Tubs Sauna Gym Patio Mtn Front Appalachian @ Mtn Creek #136 Vernon 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff B. CA $327 CA $652 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Vernon-Hotels-Appalachian-Mtn-Creek-Pool-Hot-Tubs-Sauna-Gym-Deck-Mtn-Front-136.h67340345.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/28000000/27690000/27682300/27682249/1cd1ebc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27690000/27682300/27682249/84330e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27690000/27682300/27682249/c107a24d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27690000/27682300/27682249/c62a123a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf Vernon 9.8/10 Exceptional (87) "Great experience" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pat M. [](https://www.expedia.ca/Vernon-Hotels-Ski-InSki-Out-Luxury-For-18-WHot-TubMnt-CreekHeated-PoolPrivate-Tennis-Crt.h27682249.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-27&endDate=2025-11-28®ionId=8864&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Middletown Hotel Reviews ![The Crossroads Hotel, Newburgh](//images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg) ### The Crossroads Hotel, Newburgh 10/10 Excellent "Convenient to West Point, clean nice staff. Beds comfy, bathroom clean. Great for the money. Allowed us early checkin to get to an event on time." [](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](//images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Very nice front desk people " [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Overlook Lodge at Bear Mountain](//images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Parking was very easy, beautiful area, very nice staff" [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Best Western Hunt's Landing Hotel Matamoras/Milford](//images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319_y.jpg) ### Best Western Hunt's Landing Hotel Matamoras/Milford 10/10 Excellent "Barbara does an excellent job with the breakfast! Plenty of hot food items and delirious options. She keeps it full and clean. She deserves a raise." [](https://expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) ## 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. ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bloomingburg](https://www.expedia.ca/Bloomingburg-Hotels-Cheap-Hotels.0-0-d3000448043-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Bloomingburg](https://www.expedia.ca/Bloomingburg-Hotels-Hotel-With-Pool.0-0-d3000448043-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Campbell Hall](https://www.expedia.ca/Campbell-Hall-Hotels-Cheap-Hotels.0-0-d6338665-tCheapHotels.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Adults-Only-Resorts.0-n553248633938969338-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Beach-Hotel.0-n553248633938969338-0-tBeachHotel.Travel-Guide-Filter-Hotels) - 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