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

Holiday Homes in Middletown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Middletown holiday homes

Living area

1. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
Wurtsboro
9.6 out of 10, Exceptional, (10 reviews)
"Came in to town for a bachelor party weekend and had a great time. Rooms were clean and nice, scenery was beautiful, and the host was very responsive. Beds were comfy but could use some more pillows. Kitchen/dining room was convenient but could definitely use a bigger fridge for people who want to bring stuff for meals. Overall great experience!"
United States
Nate R.
The price is AU$522
includes taxes & fees
7 Sept - 8 Sept
Hike & Fish: Outdoor Retreat Near Trails
Interior

2. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.8 out of 10, Excellent, (22 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is AU$221
includes taxes & fees
14 Sept - 15 Sept
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior

3. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (20 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is AU$204
includes taxes & fees
7 Sept - 8 Sept
Trails Head Tiny House
Beach

4. Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.8 out of 10, Exceptional, (41 reviews)
"Very thoughtfully appointed and lovingly maintained. Excellent value with lots of extras. I travelled in July, and the lake was amazing"
United States
Olga
The price is AU$331
includes taxes & fees
8 Sept - 9 Sept
Beaver Lake Escape
Interior

5. Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (15 reviews)
"It was great! "It's about a whale"."
United States
jwinegra W.
The price is AU$224
includes taxes & fees
10 Sept - 11 Sept
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Property grounds

6. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
9.0 out of 10, Wonderful, (4 reviews)
"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"
United States
Andie C.
The price is AU$213
includes taxes & fees
7 Sept - 8 Sept
Glamping Tent & Campsite by Minnewaska State Park
Interior

7. Big Stone House in Charming Catskills Village

Big Stone House in Charming Catskills Village
Wurtsboro
6.4 out of 10, (5 reviews)
"It was a great time"
United States
cesar s.
The price is AU$600
includes taxes & fees
14 Sept - 15 Sept
Big Stone House in Charming Catskills Village
Interior

8. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (42 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is AU$252
includes taxes & fees
10 Sept - 11 Sept
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior

9. Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.4 out of 10, Very good, (17 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!! Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
United States
Daisy
The price is AU$211
includes taxes & fees
7 Sept - 8 Sept
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Exterior

10. Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Vernon Township
9.4 out of 10, Exceptional, (60 reviews)
"The area is very convenient for doing outdoor activities. Room was clean."
United States
Siyu
The price is AU$426
includes taxes & fees
10 Sept - 11 Sept
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Outdoor spa tub

11. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (66 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is AU$837
includes taxes & fees
8 Sept - 9 Sept
Country House w/Hot Tub, Deck, Grill & Fire Pit
Interior

12. Scenic Views & River Access, Cozy River Home

Scenic Views & River Access, Cozy River Home
Montague
9.0 out of 10, Wonderful, (18 reviews)
"House was very homey feeling, very dog friendly with large yard."
United States
Catherine F.
The price is AU$260
includes taxes & fees
7 Sept - 8 Sept
Scenic Views & River Access, Cozy River Home
Interior

13. Cozy Riverside View House

Cozy Riverside View House
Montague
6.6 out of 10, (7 reviews)
"Great place and price. Stayed with my friends and we had a great time. The river view was amazing. House was clean and rooms were spacious. Cooktop worked fine and the dishwasher was working fine as well. Heater was functioning warm enough for 30F below. Great place and value for the stay."
United States
Dongjoo K.
The price is AU$260
includes taxes & fees
8 Sept - 9 Sept
Cozy Riverside View House
Property grounds

14. Rare River Views & Access, Cabin by Eden Islands

Rare River Views & Access, Cabin by Eden Islands
Montague
9.2 out of 10, Wonderful, (15 reviews)
"Host was accessible and very nice location to enjoy what nature brings."
United Kingdom
Rohan L.
The price is AU$275
includes taxes & fees
14 Sept - 15 Sept
Rare River Views & Access, Cabin by Eden Islands
Outdoor dining

15. Forest and River Side Tranquil House

Forest and River Side Tranquil House
Montague
7.8 out of 10, Good, (19 reviews)
"Wonderful place to relax! The location is convenient, the house is clean, cozy, and exactly as described. The hosts were very attentive and always ready to help. Great value for the price. We definitely recommend this place and would love to come back again!"
United Kingdom
Otabek K.
The price is AU$260
includes taxes & fees
7 Sept - 8 Sept
Forest and River Side Tranquil House
Private kitchen

16. Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and really cute place. "
United States
Katie C.
The price is AU$659
includes taxes & fees
28 Sept - 29 Sept
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Living area

17. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
9.8 out of 10, Exceptional, (8 reviews)
"Great space! Very nicely decorated. Host was very responsive and answered questions quickly. Also close to a great bakery and coffee shop!"
United States
Julie
The price is AU$370
includes taxes & fees
14 Sept - 15 Sept
Zen House at the Mountain Ridge
Terrace/patio

18. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (11 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AU$546
includes taxes & fees
8 Sept - 9 Sept
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds

19. Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (60 reviews)
"Had a wonderful time! Loved our stay at this beautiful river front property!"
United States
Debbie M.
The price is AU$560
includes taxes & fees
21 Sept - 22 Sept
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
Living area

20. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (38 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is AU$610
includes taxes & fees
7 Sept - 8 Sept
The DeVita House Est. 1900
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"I love staying at Bear mountain. The cottages are sometimes disappointing depending on which unit you get. This time the temperature was cold at night and there are no controls to regulate it. The building is regulated by one thermostat which is only controlled the facility. Also the bathroom was ridiculously small. The door opened in and if the door was open there literally was no room to actually stand in the bathroom. Smaller than the bathroom in my camper."
Sandra 2-night trip
Posted 6 hours ago
Overlook Lodge at Bear Mountain

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
403
Accommodation
470 Holiday Homes
Lowest Price
AU$204
Highest Price
AU$837