Photo by Vincent Ramundo

Search Middletown Cottages

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

Cottages in Middletown

Exterior
Hello Small Stone
Hello Small Stone
9.6 out of 10, Exceptional, (5)
"The house has a lot of character and the outdoor areas are really peaceful. The owner just needs to resolve the issue with sulfur in the water because the rotten egg smell is too strong to tolerate."
United States
David
$369 nightly
The price is $417
Nov 5 - Nov 6
Total with taxes and fees
Hello Small Stone
Exterior
Cozy Haven: A Romantic Retreat in our Tiny House!
Cozy Haven: A Romantic Retreat in our Tiny House!
7.0 out of 10, Good, (9)
"I love the place but the cleanliness was bad, we found a condom under the bed and there was also blood on the bed sheets and a yellow stain on the bed. I’m sorry but for the price I expected something better than this."
United States
Jeferson Eleazar P.
$254 nightly
The price is $300
Nov 4 - Nov 5
Total with taxes and fees
Cozy Haven: A Romantic Retreat in our Tiny House!
Children's area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (11)
"Wonderful cottage - lots of natural light - well equipped - great shower- comfortable beds- near Legoland - affordable- beautiful surroundings with great sunsets and sunrises - "
United States
Teresa
$281 nightly
The price is $293
Nov 4 - Nov 5
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
9.4 out of 10, Exceptional, (11)
"Peaceful, comfortable, serene, just what we were looking for...felt like home."
United States
Blanche R.
$247 nightly
The price is $280
Nov 4 - Nov 5
Total with taxes and fees
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
House (1 Bedroom) | Interior
Hike & Fish: Outdoor Retreat Near Trails
Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
$271 nightly
The price is $306
Nov 4 - Nov 5
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
Exterior
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
10.0 out of 10, Exceptional, (1)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
$191 nightly
The price is $215
Nov 4 - Nov 5
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Terrace/patio
Cozy Cottage with Woodstock Scavenger Hunt
Cozy Cottage with Woodstock Scavenger Hunt
10.0 out of 10, Exceptional, (6)
"The property was perfect for our overnight stay. Needed a place to stay after a concert at Bethel Woods and this home met our needs. Very cute and we really enjoyed the Woodstock vibe. The scavenger hunt was a fun added touch."
United States
Kimberly N.
$247 nightly
The price is $278
Nov 5 - Nov 6
Total with taxes and fees
Cozy Cottage with Woodstock Scavenger Hunt
Outdoor dining
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
2.0 star property
8.8 out of 10, Excellent, (3)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$423 nightly
The price is $478
Nov 4 - Nov 5
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Exterior
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
9.4 out of 10, Exceptional, (12)
"The Dream Cottage at the Gunks is a perfect place for a cozy stay in a scenic location. Everything was very clean and decorated with good taste. Although we were not there much due to how much we did over the weekend, our time there was very pleasant. I highly recommend staying at this property."
United States
kim h.
$207 nightly
The price is $210
Nov 4 - Nov 5
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Outdoor dining
Lakefront | Sport Courts | HotTub | GameRoom
Lakefront | Sport Courts | HotTub | GameRoom
10.0 out of 10, Exceptional, (33)
"It's a gem place that offers adventure for kids and relaxing for adults. Anyone could have awonderful time with family or friends. Definitel friends! "
United States
Valbona S.
$816 nightly
The price is $889
Nov 10 - Nov 11
Total with taxes and fees
Lakefront | Sport Courts | HotTub | GameRoom
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (124)
"Great place and host!"
United States
Jacqueline
$272 nightly
The price is $308
Nov 9 - Nov 10
Total with taxes and fees
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.
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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Nice and quiet "
Yoan 2-night trip
Posted 13 hours ago
Hampton Inn Harriman Woodbury

Find out more about Middletown

Middletown Cottages information

Number of reviews
184
Accommodation
136 Cottages
Lowest Price
$210
Highest Price
$889

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.

Explore a world of travel with Expedia