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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Middletown holiday homes

A modern hotel room with a large bed, a desk, a chair, a TV, and a wardrobe.

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

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
The price is HK$841
HK$1,794 total
includes taxes & fees
1 Oct - 2 Oct
The Columbus Hotel - The Courtyard Suite - 89-303
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

2. 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, (19 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 HK$699
HK$1,217 total
includes taxes & fees
28 Sept - 29 Sept
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
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)
"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 HK$1,294
HK$2,600 total
includes taxes & fees
28 Sept - 29 Sept
Hike & Fish: Outdoor Retreat Near Trails
A window with a view of a green, leafy outdoor area, possibly a garden or park.

4. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (21 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is HK$628
HK$1,057 total
includes taxes & fees
28 Sept - 29 Sept
Trails Head Tiny House
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

5. 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, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is HK$459
HK$997 total
includes taxes & fees
29 Sept - 30 Sept
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

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

Rare River Views & Access, Cabin by Eden Islands
Montague
9.0 out of 10, Wonderful, (16 reviews)
"Host was accessible and very nice location to enjoy what nature brings."
United Kingdom
Rohan L.
The price is HK$1,082
HK$1,539 total
includes taxes & fees
1 Oct - 2 Oct
Rare River Views & Access, Cabin by Eden Islands
A hot tub in a lush garden with a stone wall and outdoor furniture.

7. 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, (67 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 HK$2,581
HK$4,465 total
includes taxes & fees
28 Sept - 29 Sept
Country House w/Hot Tub, Deck, Grill & Fire Pit
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (12 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is HK$981
HK$2,969 total
includes taxes & fees
30 Sept - 1 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A room with a chandelier, a sofa, a table, and a cabinet.

9. 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, (23 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is HK$808
HK$1,340 total
includes taxes & fees
27 Oct - 28 Oct
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A lakeside scene with a boat and a chair on the shore.

10. Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.6 out of 10, Exceptional, (42 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 HK$1,165
HK$1,929 total
includes taxes & fees
30 Sept - 1 Oct
Beaver Lake Escape
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.

11. 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 HK$769
HK$2,678 total
includes taxes & fees
28 Sept - 29 Sept
Big Stone House in Charming Catskills Village

12. Cozy Riverside View House

Cozy Riverside View House
Montague
6.8 out of 10, (8 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 HK$1,012
HK$1,455 total
includes taxes & fees
28 Sept - 29 Sept
Cozy Riverside View House

13. Scenic Views & River Access, Cozy River Home

Scenic Views & River Access, Cozy River Home
Montague
9.2 out of 10, Wonderful, (19 reviews)
"House was very homey feeling, very dog friendly with large yard."
United States
Catherine F.
The price is HK$1,012
HK$1,455 total
includes taxes & fees
28 Sept - 29 Sept
Scenic Views & River Access, Cozy River Home

14. 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 HK$1,012
HK$1,455 total
includes taxes & fees
28 Sept - 29 Sept
Country Comfort Cabin, Delaware River Eden Islands
A hotel with a swimming pool, green lawns, and a hilly backdrop.

15. 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 HK$1,122
HK$2,298 total
includes taxes & fees
2 Oct - 3 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

16. Forest and River Side Tranquil House

Forest and River Side Tranquil House
Montague
7.8 out of 10, Good, (19 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 HK$1,012
HK$1,455 total
includes taxes & fees
28 Sept - 29 Sept
Forest and River Side Tranquil House
A modern kitchen with a white island, stainless steel appliances, and wooden flooring.

17. Nurser * Private Garden * Minutes to Minnewaska

Nurser * Private Garden * Minutes to Minnewaska
Pine Bush
10.0 out of 10, Exceptional, (4 reviews)
"Nice property, very close to Sam’s Point trailheads. We were there to hike, so this was perfect. We would definitely book again."
United States
Amy L.
The price is HK$1,312
HK$4,571 total
includes taxes & fees
1 Oct - 2 Oct
Nurser * Private Garden * Minutes to Minnewaska
A kitchen with wooden ceiling beams, a black countertop, and a white backsplash.

18. 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 HK$699
HK$1,934 total
includes taxes & fees
28 Sept - 29 Sept
Sweet Suite Tiny House w/ Zen Vibes on Quiet Lake
A forest campsite with a tent, a fire pit, and a bench.

19. 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 HK$671
HK$1,190 total
includes taxes & fees
7 Oct - 8 Oct
Glamping Tent & Campsite by Minnewaska State Park
A covered deck with outdoor seating and string lights.

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

Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck
Sparrow Bush
10.0 out of 10, Exceptional, (7 reviews)
"Great stay, host was very responsive, would definitely stay again! "
United States
Shriraj S.
The price is HK$1,687
HK$2,086 total
includes taxes & fees
29 Sept - 30 Sept
Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"The room was a little warm. There was no way to make it cooler."
Marilyn 1-night trip
Posted 14 hours ago
Overlook Lodge at Bear Mountain

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
326
Accommodation
467 Vacation Homes
Lowest Price
HK$997
Highest Price
HK$4,571

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