Photo by Vincent Ramundo

Search Middletown Cottage Rentals from CA $128

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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

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, (106)
"Great place and host!"
The price is CA $242
CA $354 total
includes taxes & fees
Feb 4 - Feb 5
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 $410
CA $805 total
includes taxes & fees
Feb 3 - Feb 4
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 $287
CA $1,150 total
includes taxes & fees
Feb 3 - Feb 4
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, (136)
"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 $238
CA $446 total
includes taxes & fees
Feb 1 - Feb 2
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 $491
CA $850 total
includes taxes & fees
Feb 23 - Feb 24
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
Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly
Fridge, microwave, oven, stovetop

Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly

6.8 out of 10, (19)
"Contacted host on the morning of stay about instructions to access house. Had not received them. Cancelled on me shortly after."
The price is CA $302
CA $560 total
includes taxes & fees
Feb 1 - Feb 2
Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly
19'Heated SwimSpa | Lake | Snow | Hikes | Firepit
Miscellaneous

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

The price is CA $128
CA $722 total
includes taxes & fees
Feb 3 - Feb 4
19'Heated SwimSpa | Lake | Snow | Hikes | Firepit
A romantic cottage and artist's retreat looking down over an enchanted lake
Interior

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."
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 $259
CA $438 total
includes taxes & fees
Feb 6 - Feb 7
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 $144
CA $187 total
includes taxes & fees
Feb 1 - Feb 2
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.
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

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, (106)
"Great place and host!"
The price is CA $242
CA $354 total
includes taxes & fees
Feb 4 - Feb 5
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Greenwoods of Warwick
Fridge, microwave, oven, stovetop

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Smart TV, fireplace

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

9.6 out of 10, Exceptional, (23)
"Great place for family ski vacation. Apt was clean, with amenities for cooking. Great fireplace. The ski areas are very kid friendly. The bunny slope was carved up into different trails for learning different skills. Didn’t need to drive to get things. Everything for a great stay was right on site."
The price is CA $230
CA $470 total
includes taxes & fees
Feb 3 - Feb 4
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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

Why book your cottage in Middletown with Expedia?
Expedia has some great cottages in Middletown, so get ready for a memorable vacay close to nature. If you’re on a budget, choose how much you’re willing to spend and the preferred star rating of your property. Or, make your way to the filters to search for cottages with a hot tub or free WiFi. We’ll help you find the perfect place whatever your trip looks like.
How can I find cheap cottages in Middletown?
Expedia is here to help you locate cheap cottages in Middletown. To discover the perfect stay in a couple of clicks, try out the filter tool to tailor your search results by budget, amenities and star rating.
What is there to do in Middletown near my cottage?
The ideal travel accessory is a well-planned schedule. Highland Lakes State Park is a wonderful place to kick-start your exploration of Middletown.