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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Middletown cottages

Exterior

Cottage in Sparrow Bush

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
9.4 out of 10, Exceptional, (11 reviews)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
United States
Nicholas G.
The price is ￥13,832
￥42,300 total
includes taxes & fees
Jan 20 - Jan 21
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Smart TV

Cottage in Goshen

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is ￥23,481
￥46,578 total
includes taxes & fees
Jan 20 - Jan 21
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior

Cottage in Kerhonkson

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
9.4 out of 10, Exceptional, (12 reviews)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is ￥14,425
￥31,407 total
includes taxes & fees
Jan 26 - Jan 27
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Outdoor dining

Cottage in Highland Lake

Lakefront | Sport Courts | HotTub | GameRoom
10.0 out of 10, Exceptional, (33 reviews)
"We had a wonderful time and definitely would recommend!"
United States
Phillip C.
The price is ￥23,560
￥131,532 total
includes taxes & fees
Jan 26 - Jan 27
Lakefront | Sport Courts | HotTub | GameRoom
Outdoor dining

Cottage in Vernon Township

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
2.0 star property
8.8 out of 10, Excellent, (3 reviews)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
The price is ￥35,577
￥75,556 total
includes taxes & fees
Jan 20 - Jan 21
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Property grounds

Cottage in Fort Montgomery

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (131 reviews)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is ￥29,727
￥48,118 total
includes taxes & fees
Jan 20 - Jan 21
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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 really enjoyed my stay at kartrie ,the staff was very pleasant and helpful. The room was clean and the bed was very comfortable. I would definitely stay again. Thanks "
Simont 1-night trip
Posted 14 hours ago
The Kartrite Resort & Indoor Waterpark

Find out more about Middletown

Middletown Cottages information

Number of reviews
184
Accommodation
134 Cottages
Lowest Price
￥31,407
Highest Price
￥131,532

Frequently asked questions

Why book your cottage in Middletown with Expedia?
We think a getaway should be a walk in the park, so if you're seeking cottages in Middletown at a competitive rate, Expedia has got your back. Keep costs down and select an inexpensive option far from the downtown buzz, or splurge on a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Middletown?
With Expedia's useful filter tool, sourcing cheap cottages in Middletown is a cinch. To discover accommodations that'll make your wallet smile, narrow down your search by budget, amenities and star rating.
What is there to do in Middletown near my cottage?
If you'd like to see the sights of Middletown, be sure to visit Orange County Fair Speedway. It's a hit among visitors and locals alike.