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Search Middletown Cottage Rentals from CA $120

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Check prices for these dates

Next weekend
Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20
In one month
Aug 1 - Aug 3
In two months
Aug 29 - Aug 31

Browse Select Middletown Cottages

Cozy Haven: A Romantic Retreat in our Tiny House!
TV, fireplace

Cozy Haven: A Romantic Retreat in our Tiny House!

7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
The price is CA $204
CA $408 total
includes taxes & fees
Jul 7 - Jul 8
Cozy Haven: A Romantic Retreat in our Tiny House!
Hello Small Stone
Exterior

Hello Small Stone

9.6 out of 10, Exceptional, (4)
"The house was great. It was nice to sit and relax by the small pond in the back."
The price is CA $245
CA $593 total
includes taxes & fees
Jul 16 - Jul 17
Hello Small Stone
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (114)
"We enjoyed our stay. The views are great and the space comfortable. It worked well for our visit with family living nearby and visiting Bear Mountain."
The price is CA $255
CA $406 total
includes taxes & fees
Jul 14 - Jul 15
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Luxury Mountain House: Pool, Theater & Outdoor Kitchen
Outdoor pool

Luxury Mountain House: Pool, Theater & Outdoor Kitchen

9.8 out of 10, Exceptional, (9)
"Was a great location for a family gathering. The pool was great. The layout of the house was awesome."
The price is CA $1,174
CA $2,138 total
includes taxes & fees
Jul 14 - Jul 15
Luxury Mountain House: Pool, Theater & Outdoor Kitchen
Charming Cottage in the Heart of the Shawangunks
Fridge, oven, stovetop, coffee/tea maker

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (12)
"Wonderful stay, exactly as advertised, everything brand new and very cozy."
The price is CA $374
CA $815 total
includes taxes & fees
Jul 11 - Jul 12
Charming Cottage in the Heart of the Shawangunks
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Terrace/patio

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

9.8 out of 10, Exceptional, (10)
"Wonderful cottage - lots of natural light - well equipped - great shower- comfortable beds- near Legoland - affordable- beautiful surroundings with great sunsets and sunrises - "
The price is CA $202
CA $391 total
includes taxes & fees
Jul 14 - Jul 15
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Miscellaneous

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

9.6 out of 10, Exceptional, (10)
"Great peaceful spot, close to a ton of outdoor activities. East check in and property was as advertised."
The price is CA $169
CA $304 total
includes taxes & fees
Jul 23 - Jul 24
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Property grounds

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

2.0 star property
8.0 out of 10, Very good, (2)
"Nice"
The price is CA $366
CA $727 total
includes taxes & fees
Jul 13 - Jul 14
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Exterior

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

The price is CA $152
CA $247 total
includes taxes & fees
Jul 7 - Jul 8
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Cozy Cottage with a Pond 2
1 bedroom, free WiFi

Cozy Cottage with a Pond 2

6.0 out of 10, (12)
"Was perfect place to stay with lots of hiking and waterfalls near by"
The price is CA $136
CA $198 total
includes taxes & fees
Jul 13 - Jul 14
Cozy Cottage with a Pond 2
Hike & Fish: Outdoor Retreat Near Trails
House (1 Bedroom) | Interior

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
The price is CA $249
CA $410 total
includes taxes & fees
Aug 5 - Aug 6
Hike & Fish: Outdoor Retreat Near Trails
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Property grounds

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

10.0 out of 10, Exceptional, (9)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
The price is CA $120
CA $379 total
includes taxes & fees
Jul 8 - Jul 9
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Cozy Cottage with Woodstock Scavenger Hunt
Terrace/patio

Cozy Cottage with Woodstock Scavenger Hunt

The price is CA $189
CA $383 total
includes taxes & fees
Jul 9 - Jul 10
Cozy Cottage with Woodstock Scavenger Hunt
Lakefront | 22 acres | HotTub | Game Room
Miscellaneous

Lakefront | 22 acres | HotTub | Game Room

10.0 out of 10, Exceptional, (32)
"We had a wonderful time and definitely would recommend!"
The price is CA $766
CA $1,796 total
includes taxes & fees
Jul 13 - Jul 14
Lakefront | 22 acres | HotTub | Game Room
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Miscellaneous

SwimSpa | Lake | Fish | Kayak | Hike | Firepit

9.6 out of 10, Exceptional, (4)
"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!"
The price is CA $338
CA $969 total
includes taxes & fees
Jul 8 - Jul 9
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
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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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.