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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Middletown holiday homes

A modern kitchen with a built-in microwave and a dining area with a table and chairs.

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

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
The price is £163
includes taxes & fees
27 Oct - 28 Oct
The Columbus Hotel - The Courtyard Suite - 89-303
A room with a sloped ceiling, wooden beams, and two windows with curtains.

2. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
8.8 out of 10, Excellent, (22 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is £96
includes taxes & fees
1 Nov - 2 Nov
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.

3. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
Wurtsboro
9.6 out of 10, Exceptional, (10 reviews)
"Clean, cozy, relaxing vibes"
United States
Daniel S.
The price is £258
includes taxes & fees
27 Oct - 28 Oct
Hike & Fish: Outdoor Retreat Near Trails
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

4. 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
8.6 out of 10, Excellent, (20 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 £123
includes taxes & fees
2 Nov - 3 Nov
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
A hot tub in a lush garden with a stone wall and outdoor furniture.

5. 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, (69 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 £399
includes taxes & fees
1 Nov - 2 Nov
Country House w/Hot Tub, Deck, Grill & Fire Pit
A circular outdoor seating area with a fire pit, surrounded by a stone border, set in a lush green forest.

6. Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Goshen
10.0 out of 10, Exceptional, (35 reviews)
"Great house, as advertised!"
United States
Steven K.
The price is £542
includes taxes & fees
1 Nov - 2 Nov
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Living room (3)

7. Scenic Views & River Access, Cozy River Home

Scenic Views & River Access, Cozy River Home
Montague
9.2 out of 10, Wonderful, (20 reviews)
"House was very homey feeling, very dog friendly with large yard."
United States
Catherine F.
The price is £142
includes taxes & fees
27 Oct - 28 Oct
Scenic Views & River Access, Cozy River Home
Beautiful Montague sunset

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

Rare River Views & Access, Cabin by Eden Islands
Montague
9.0 out of 10, Wonderful, (17 reviews)
"Host was accessible and very nice location to enjoy what nature brings."
United Kingdom
Rohan L.
The price is £142
includes taxes & fees
28 Oct - 29 Oct
Rare River Views & Access, Cabin by Eden Islands
A two-story house with a front porch and a landscaped garden.

9. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (18 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is £109
includes taxes & fees
28 Oct - 29 Oct
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Patio (2)

10. Forest and River Side Tranquil House

Forest and River Side Tranquil House
Montague
7.8 out of 10, Good, (20 reviews)
"Over all ok property. A bit outdated but comfortable. Check on and out very smooth and easy."
United States
Connie B.
The price is £142
includes taxes & fees
27 Oct - 28 Oct
Forest and River Side Tranquil House
Fireplace (4)

11. Cozy Riverside View House

Cozy Riverside View House
Montague
6.8 out of 10, (8 reviews)
"The house was ok but some of the lights did not work and was difficult to have someone come out. The river access was difficult and hard to understand the directions."
United States
Chris M.
The price is £142
includes taxes & fees
28 Oct - 29 Oct
Cozy Riverside View House
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 £336
includes taxes & fees
1 Nov - 2 Nov
Big Stone House in Charming Catskills Village
A clear blue pool surrounded by rocks and trees.

13. Spectacular Historic Mansion w/Pool&Tennis

Spectacular Historic Mansion w/Pool&Tennis
Goshen
10.0 out of 10, Exceptional, (20 reviews)
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
United States
Aditya U.
The price is £1,951
includes taxes & fees
1 Nov - 2 Nov
Spectacular Historic Mansion w/Pool&Tennis
A room with a chandelier, a sofa, a table, and a cabinet.

14. 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, (24 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is £122
includes taxes & fees
2 Nov - 3 Nov
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A house with a covered porch, stone pillars, and a black railing.

15. Cozy Huguenot Hideaway

Cozy Huguenot Hideaway
Huguenot
The price is £440
includes taxes & fees
2 Nov - 3 Nov
Cozy Huguenot Hideaway
A tent with a central pole, a view of the forest through the entrance, and a bed with patterned bedding.

16. 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 £116
includes taxes & fees
27 Oct - 28 Oct
Glamping Tent & Campsite by Minnewaska State Park
A covered deck with outdoor seating and string lights.

17. Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck

Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck
Sparrow Bush
9.4 out of 10, Exceptional, (9 reviews)
"Great stay, host was very responsive, would definitely stay again! "
United States
Shriraj S.
The price is £191
includes taxes & fees
27 Oct - 28 Oct
Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck
20250709 000242657 iOS

18. Country Comfort Cabin, Delaware River Eden Islands

Country Comfort Cabin, Delaware River Eden Islands
Montague
6.6 out of 10, (4 reviews)
"This was a fine stay at a no-frills cabin home in the tri-states. Easy check-in and out and the amenities you'd expect for a low key weekend. A word of warning for those sensitive to cigarette smoke: this very much seems like a former smokers home and the smell took me back decades (not in a good way)."
United States
Anonymous traveller
The price is £142
includes taxes & fees
27 Oct - 28 Oct
Country Comfort Cabin, Delaware River Eden Islands
A modern living room with a stone fireplace, a flat-screen TV, and a sliding glass door leading to an outdoor area.

19. Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.6 out of 10, Exceptional, (44 reviews)
"It was amazing quiet, clean, in a great location. Will go back again."
United States
GinaMarie C.
The price is £195
includes taxes & fees
27 Oct - 28 Oct
Beaver Lake Escape
A hotel with a swimming pool, green lawns, and a hilly backdrop.

20. 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, (64 reviews)
"Really nice retreat , not far from NYC, place very clean , great pool ,"
United States
Jakub S.
The price is £232
includes taxes & fees
1 Nov - 2 Nov
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

10/10 Excellent
"I took my daughter here for her birthday weekend last week and she had a blast!! The resort has everything a six year old would want. Food, ice cream, plenty of games and the water park was fun. Pretty nice bar downstairs in the main lobby and inside the water park for us adults. Drinks cost what you’d expect at a water park resort about $12-15 on average ."
Anton L 1-night trip
Posted 7 hours ago
The Kartrite Resort & Indoor Waterpark

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
337
Accommodation
461 Holiday Homes
Lowest Price
£96
Highest Price
£1,951