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Compare 117 Cottages in Middletown with updated reviews, rates, and availability.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (106)
"Great place and host!"
The price is SAR 631
SAR 923 total
includes taxes & fees
15 Jan - 16 Jan
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Mountain House Escape - 1 Hour from NYC
Exterior

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)
"We had an extremely great time at this rental house and were blown away how the layout of the house provided all our conveniences. It was clean spacious and beautifully arranged as seen in pics online . It was our mountain escape dream and we would definitely recommend and stay here again ."
Mountain View escape
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
The Cottage at Millpond Falls is a romantic getaway -- an luxury experience you won't forget.

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
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Private kitchen

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 SAR 619
SAR 1,173 total
includes taxes & fees
18 Jan - 19 Jan
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Dining

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 SAR 1,047
SAR 2,067 total
includes taxes & fees
21 Jan - 22 Jan
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Lazy River Cottage on the Delaware River
Private river bank with seatings

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (134)
"Cottage was great! Quiet, clean and nicely renovated. "
Lazy River Cottage on the Delaware River
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Home Sweet Home ...

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
Stony Kill Ranch - Bohemian Paradise on Minnewaska

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
Historic 1800's Cornwall-On-Hudson Cottage!
Cornwall-On-Hudson Vacation Rental | 2BR | 2BA | Stairs Required | 2,000 Sq Ft

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!
Lakefront | 22 acres | HotTub | Game Room
Living room with fireplace, 55" smart TV, queen+ pullout sofa, and picturesque view of the lake

Lakefront | 22 acres | HotTub | Game Room

10.0 out of 10, Exceptional, (28)
"We had an amazing stay at the Highland Lake property! Everything exceeded our expectations, not only was every small detail considered but the host was extremely responsive as well. We especially enjoyed all the amenities the lake house had to offer, making our first stay in the Catskills a huge success. We would highly recommend to anyone looking to stay in the area! "
The price is SAR 747
SAR 3,033 total
includes taxes & fees
15 Jan - 16 Jan
Lakefront | 22 acres | HotTub | Game Room
Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly
Living area

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 SAR 788
SAR 1,459 total
includes taxes & fees
11 Jan - 12 Jan
Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly
Cozy Cottage with a Pond 2
Property grounds

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 SAR 375
SAR 488 total
includes taxes & fees
16 Jan - 17 Jan
Cozy Cottage with a Pond 2
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River
Property grounds

Tiny House on Spectacular Riverfront Property - Private Access to Delaware River

9.6 out of 10, Exceptional, (32)
"It was a lovely stay with easy access to the water. I recommend walking to the antique store nearby and consider bringing your own tube and life jacket."
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!

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!
Cozy Cottage with a Pond
Property grounds

Cozy Cottage with a Pond

10.0 out of 10, Exceptional, (1)
"My husband and I enjoyed two nights in this quiet and cozy cottage. I LOVED spending time on the porch looking out onto the beautiful pond and watching the stars at night. This was a perfect getaway and break from the busy world and look forward to future trips here again."
Cozy Cottage with a Pond
A romantic cottage and artist's retreat looking down over an enchanted lake
Stunning views

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

9.4 out of 10, Exceptional, (96)
"We cannot overstate how perfect this cottage was for us to have a quiet retreat. The place has all you need to unwind and drink in the view. The owners went above and beyond (we stayed 2 full months!). Everything was lovely, thanks Julia :)"
A romantic cottage and artist's retreat looking down over an enchanted lake
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
Living area

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!
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Nothing more beautiful than Fall foliage

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

10.0 out of 10, Exceptional, (9)
"If you are looking for peace, quiet, & nature then look no further. We will definitely go back when traveling in that area."
The price is SAR 369
SAR 1,016 total
includes taxes & fees
4 Feb - 5 Feb
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Charming Lakefront Cottage On Masten lake
Outdoor dining

Charming Lakefront Cottage On Masten lake

9.8 out of 10, Exceptional, (34)
"We really enjoyed this cozy little college next to the lake. It was a perfect place to stay when going to multiple nights of concerts at Bethel Woods. We would love to return some time. The owner is kind and communicative and the entire process was very stress free. Great little place for a couple."
Charming Lakefront Cottage On Masten lake
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

Cottage Suites
Room

Cottage Suites

3.0 star property
8.0 out of 10, Very Good, (3)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
Cottage Suites
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (106)
"Great place and host!"
The price is SAR 631
SAR 923 total
includes taxes & fees
15 Jan - 16 Jan
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Trails Head Tiny House
Updated picture of the exterior with the extended deck.

Trails Head Tiny House

9.2 out of 10, Wonderful, (11)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is SAR 297
SAR 465 total
includes taxes & fees
12 Jan - 13 Jan
Trails Head Tiny House
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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