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Check prices for these dates

Next weekend
Mar 14 - Mar 16
In two weeks
Mar 21 - Mar 23
In one month
Apr 4 - Apr 6
In two months
May 2 - May 4

Browse Select Middletown Cottages

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, (107)
"Spectacular view and very convenient to USMA. "
The price is CA $243
CA $353 total
includes taxes & fees
Mar 9 - Mar 10
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Mountain House Escape - 1 Hour from NYC
Outdoor pool

Mountain House Escape - 1 Hour from NYC

10.0 out of 10, Exceptional, (7)
"We recently had the pleasure of staying at Deer Hill in Warwick, NY, and it truly exceeded our expectations. The property is set on three-acre expanse in a lovely, and ultra-quiet neighborhood. It was an ideal home for our annual family gathering, which includes our 3 adult children, spouses and two young grandchildren. The large in-ground pool was a hit, and was a source of fun and relaxation throughout our stay. The pool has a shallow end and an 8-foot deep end. The spacious great room served...
Mountain House Escape - 1 Hour from NYC
Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (46)
"Can’t wait to go back, if I could move this home to Myrtle Beach I would. Fantastic communication with homeowner, great location. Homeowner keeps the home stocked with goodies, extra plus! Very cozy and Quiet it’s a 10 Star "
Mountain View escape
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 $362
CA $741 total
includes taxes & fees
Mar 4 - Mar 5
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Pool

Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick

10.0 out of 10, Exceptional, (142)
"Such a beautiful location. The cottage is quant while having all the modern updates. The hosts have carefully left an array of coffee and welcome goodies, including fresh eggs from their ducks. Will be back! "
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Lakefront | 22 acres | HotTub | Game Room
Aerial view

Lakefront | 22 acres | HotTub | Game Room

10.0 out of 10, Exceptional, (28)
"Truly a great getaway from the city for relaxation and nature. A beautiful property with great amenities to make it feel like home. The host checked in often and was very responsive. Great place to bring kids and enjoy the outdoors even in the cold winter! "
The price is CA $215
CA $1,071 total
includes taxes & fees
Mar 5 - Mar 6
Lakefront | 22 acres | HotTub | Game Room
Lazy River Cottage on the Delaware River
Fireplace, books, music library, stereo

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (137)
"what a lovely lovely cottage by the lake very clean all the amenities inside the house. Contact with the host was amazing. Fire pit fireplace very lovely place. Will stay there again."
Lazy River Cottage on the Delaware River
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Lake

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (98)
"Great Highland Lakes Cottage! Clean & well stocked kitchen. Be careful going up or down Breakneck Rd. Thus time of year every view is beautiful! We did lots of small road trips taking in the sites and autumnal views!!"
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Historic 1800's Cornwall-On-Hudson Cottage!
Outdoor dining

Historic 1800's Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (22)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800's Cornwall-On-Hudson Cottage!
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Terrace/patio

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

9.8 out of 10, Exceptional, (9)
"We had a great stay in this cozy cabin! The beds were comfortable and the views of the farm and deer were beautiful ! Communication with Ginny was quick and she let us adjust our dates of stay when needed. 😊"
The price is CA $239
CA $443 total
includes taxes & fees
Mar 11 - Mar 12
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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, (7)
"My bridesmaids and I stayed here the night before my wedding and my husband and I the night of my wedding ..it is absolutely beautiful and private just what we wanted! Would definitely stay here again!"
The price is CA $289
CA $671 total
includes taxes & fees
Mar 4 - Mar 5
Charming Cottage in the Heart of the Shawangunks
Stony Kill Ranch - Bohemian Paradise on Minnewaska
Fridge, microwave, oven, stovetop

Stony Kill Ranch - Bohemian Paradise on Minnewaska

7.4 out of 10, Good, (3)
"Some friends and our pups were looking to spend a nice weekend upstate with our dogs to relax and spend time, and this place was perfect. The location is GREAT! It is near hiking trails, some breweries/orchards and while we didn’t go to dinner, there were restaurants around as well. The house was as described, spacious and had a lot to offer. We loved spending time in the hot tub and around the fire pit. The jam shed was a lot of fun for some in our group too! Check in was easy and when we had a...
Stony Kill Ranch - Bohemian Paradise on Minnewaska
19'Heated SwimSpa | Lake | Snow | Hikes | Firepit
Miscellaneous

19'Heated SwimSpa | Lake | Snow | Hikes | Firepit

The price is CA $129
CA $715 total
includes taxes & fees
Mar 6 - Mar 7
19'Heated SwimSpa | Lake | Snow | Hikes | Firepit
A romantic cottage and artist's retreat looking down over an enchanted lake
Property grounds

A romantic cottage and artist's retreat looking down over an enchanted lake

9.4 out of 10, Exceptional, (96)
"It was an awesome stay we loved the couple days we got to spend there!!"
A romantic cottage and artist's retreat looking down over an enchanted lake
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
Miscellaneous

Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!

10.0 out of 10, Exceptional, (24)
"We loved our stay at this beautiful home! The property was nicely situated in a wooded neighborhood and the inside was very clean. We will definitely be returning. Also highly recommend a walk around the nearby lake and a visit to some local breweries! "
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
Outdoor spa tub

2 Lake Cabins | Pool+HotTub | Game Room | 23acs

10.0 out of 10, Exceptional, (1)
"Gorgeous property for a family reunion. Host was very accommodating and responsive. Lots of fun amenities and room for everyone to spread out. Great open space on the lake but still felt private and quiet. Wifi throughout entire property. Absolutely recommend and would definitely book again."
The price is CA $577
CA $1,926 total
includes taxes & fees
Mar 27 - Mar 28
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
Hello Small Stone
Exterior

Hello Small Stone

9.6 out of 10, Exceptional, (4)
"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."
The price is CA $260
CA $438 total
includes taxes & fees
Mar 5 - Mar 6
Hello Small Stone
Cozy Cottage with a Pond 2
1 bedroom, free WiFi

Cozy Cottage with a Pond 2

6.0 out of 10, (12)
"I don't like to put negative energy out into the Universe BUT... from the steep slippery stairs to the upside down entry door to the lack of water- no water at all in the morning- then the sulfuric water. And then there was the creepy cat picture on the wall. We named the place the S King Lodge after our favorite horror writer. The stairs alone are a red red flag. No light at the top of these steep, jankily constructed danger. And then theres the inside for which the only word that suits the...
The price is CA $145
CA $188 total
includes taxes & fees
Mar 4 - Mar 5
Cozy Cottage with a Pond 2
Magical, all season, multilevel treehouse on beautiful 120 acre property.
Exterior

Magical, all season, multilevel treehouse on beautiful 120 acre property.

10.0 out of 10, Exceptional, (3)
"Our two young children absolutely loved our stay at the treehouse! Such a unique and fun way to spend a few days in the woods!"
Magical, all season, multilevel treehouse on beautiful 120 acre property.
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
Exterior

NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!

10.0 out of 10, Exceptional, (5)
"The house is even more beautiful than the photos. From the spa-like bathrooms, to toys and books for kids, to the little extra amenities like qtips and bandaids, it was the perfect getaway for everyone in our party of all ages."
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
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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Other property types in Middletown

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
5 bedrooms, desk, iron/ironing board, free WiFi

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (70)
"This beautiful getaway was just what we needed. Fresh air, nature, and a gorgeous home. Already planning our next trip back..."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
The Philip Johnson Wolfhouse
Interior

The Philip Johnson Wolfhouse

10.0 out of 10, Exceptional, (3)
"This house is an architectural gem with great views to the Hudson river and very close to Dia Beacon and really nice hikes. We were a group of 7 and really enjoyed our time together during our stay. Jeremy was really nice and accommodating. I highly recommend this house."
The Philip Johnson Wolfhouse
Trails Head Cabin
Exterior

Trails Head Cabin

9.8 out of 10, Exceptional, (76)
"We had a wonderful stay! The property managers were wonderful. We stayed the night for a birthday celebration and they made the experience extra special. Will definitely return!"
The price is CA $146
CA $258 total
includes taxes & fees
Mar 4 - Mar 5
Trails Head Cabin
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.

Frequently asked questions

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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?
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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.