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

Search Holiday Homes in Middletown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Middletown holiday homes

A modern kitchen with a built-in microwave, a refrigerator, and a sink. There is a hallway leading to a bedroom with a bed and a window.

1. The Columbus Hotel - The Courtyard Suite - 89-303

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
The price is £159
includes taxes & fees
9 Sept - 10 Sept
The Columbus Hotel - The Courtyard Suite - 89-303
A room with a chandelier, a sofa, a table, and a cabinet.

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 £119
includes taxes & fees
14 Sept - 15 Sept
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A window with a view of a green, leafy outdoor area, possibly a garden or park.

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 £102
includes taxes & fees
15 Sept - 16 Sept
Trails Head Tiny House
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

4. 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 £276
includes taxes & fees
9 Sept - 10 Sept
Hike & Fish: Outdoor Retreat Near Trails
A fireplace with logs, a vase with flowers, and candles on a woven mat.

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 £120
includes taxes & fees
10 Sept - 11 Sept
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

6. 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 £133
includes taxes & fees
10 Sept - 11 Sept
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
A lakeside scene with a boat and a chair on the shore.

7. 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 £179
includes taxes & fees
9 Sept - 10 Sept
Beaver Lake Escape
A forest campsite with a tent, a fire pit, and a bench.

8. 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 £115
includes taxes & fees
9 Sept - 10 Sept
Glamping Tent & Campsite by Minnewaska State Park
A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

9. 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 £172
includes taxes & fees
14 Sept - 15 Sept
Zen House at the Mountain Ridge
A hotel with a swimming pool, green lawns, and a hilly backdrop.

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 £231
includes taxes & fees
10 Sept - 11 Sept
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
A hot tub in a lush garden with a stone wall and outdoor furniture.

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 £440
includes taxes & fees
13 Sept - 14 Sept
Country House w/Hot Tub, Deck, Grill & Fire Pit
A cozy room with a stone wall, wooden ceiling, and a large window. There is a round rug, a chair, and a small table with a vase of flowers.

12. 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 £321
includes taxes & fees
9 Sept - 10 Sept
Big Stone House in Charming Catskills Village
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

13. 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 £114
includes taxes & fees
14 Sept - 15 Sept
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
A modern kitchen with a central island, bar stools, a round table, and a window with a view.

14. 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 £352
includes taxes & fees
28 Sept - 29 Sept
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

15. 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 £295
includes taxes & fees
9 Sept - 10 Sept
House on the Babbling Brook- Quiet 2BR + King Bed!

16. 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 £148
includes taxes & fees
14 Sept - 15 Sept
Rare River Views & Access, Cabin by Eden Islands

17. 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 £140
includes taxes & fees
10 Sept - 11 Sept
Cozy Riverside View House
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

18. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (39 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is £335
includes taxes & fees
10 Sept - 11 Sept
The DeVita House Est. 1900
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

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 £313
includes taxes & fees
21 Sept - 22 Sept
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
A kitchen with wooden ceiling beams, a black countertop, and a white backsplash.

20. Sweet Suite Tiny House w/ Zen Vibes on Quiet Lake

Sweet Suite Tiny House w/ Zen Vibes on Quiet Lake
Woodridge
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our two night stay here. The tiny house was well maintained. "
United States
Chris D.
The price is £214
includes taxes & fees
9 Sept - 10 Sept
Sweet Suite Tiny House w/ Zen Vibes on Quiet Lake
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

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

8/10 Good
"Room was nice and clean no issues and ample space."
Rodolfo 1-night trip
Posted 1 hour ago
Holiday Inn Express Hotel & Suites Chester by IHG

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
407
Accommodation
486 Holiday Homes
Lowest Price
£102
Highest Price
£440