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Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Middletown cottages

Exterior

Cottage in Middletown

Hello Small Stone
9.6 out of 10, Exceptional, (5 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is ￥28,411
￥69,279 total
includes taxes & fees
Apr 8 - Apr 9
Hello Small Stone
Exterior

Cottage in Kerhonkson

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
9.4 out of 10, Exceptional, (13 reviews)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is ￥17,615
￥32,989 total
includes taxes & fees
Apr 19 - Apr 20
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
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 ￥17,047
￥45,891 total
includes taxes & fees
Apr 15 - Apr 16
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)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is ￥23,729
￥46,750 total
includes taxes & fees
Mar 24 - Mar 25
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
House (1 Bedroom) | Interior

Cottage in Westbrookville

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
The price is ￥26,044
￥48,576 total
includes taxes & fees
Apr 13 - Apr 14
Hike & Fish: Outdoor Retreat Near Trails
Property grounds

Cottage in Fort Montgomery

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (132 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is ￥29,674
￥48,032 total
includes taxes & fees
Mar 23 - Mar 24
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Outdoor dining

Cottage in Vernon Township

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
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 ￥35,514
￥75,738 total
includes taxes & fees
Mar 24 - Mar 25
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Outdoor dining

Cottage in Highland Lake

Lakefront | Sport Courts | HotTub | GameRoom
10.0 out of 10, Exceptional, (33 reviews)
"This property is absolutely beautiful. The check in process was easy and the host was super helpful and sweet! Highly recommend this place."
United States
Christina V.
The price is ￥23,809
￥134,130 total
includes taxes & fees
Mar 26 - Mar 27
Lakefront | Sport Courts | HotTub | GameRoom
Terrace/patio

Cottage in Highland Lake

SwimSpa | Sport Courts | Lake | Fishing | Firepit
9.6 out of 10, Exceptional, (8 reviews)
"Enjoyed our stay very much! Would highly recommend for someone seeking a nice quite get-away. Very nice Swim-spa for relaxation, many board games. We look forward to returning!"
United States
Dave M.
The price is ￥32,917
￥136,151 total
includes taxes & fees
Apr 6 - Apr 7
SwimSpa | Sport Courts | Lake | Fishing | Firepit
Property grounds

Cottage in Bloomingburg

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
10.0 out of 10, Exceptional, (1 review)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
The price is ￥22,098
￥33,731 total
includes taxes & fees
Apr 1 - Apr 2
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
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

Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent
"We were only supposed to stay for a little rest but ended up getting stuck in a snow storm. Ended up staying 2 extra a nights. Breakfast was great. Staff were all very friendly. Clean & well stocked. "
Theresa 1-night trip
Posted 3 hours ago
Best Western Hunt's Landing Hotel Matamoras/Milford

Find out more about Middletown

Middletown Cottages information

Number of reviews
205
Accommodation
134 Cottages
Lowest Price
￥32,989
Highest Price
￥136,151

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.