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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 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, (107)
"Spectacular view and very convenient to USMA. "
The price is SAR 630
SAR 919 total
includes taxes & fees
17 Feb - 18 Feb
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)
"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
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 938
SAR 1,926 total
includes taxes & fees
4 Mar - 5 Mar
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
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
Lakefront | 22 acres | HotTub | Game Room
Hot tub and fire pit adjacent to screened in veranda

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 SAR 780
SAR 3,035 total
includes taxes & fees
18 Feb - 19 Feb
Lakefront | 22 acres | HotTub | Game Room
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, (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
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
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!
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 1,164 total
includes taxes & fees
17 Feb - 18 Feb
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Charming Cottage in the Heart of the Shawangunks
Exterior

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 SAR 750
SAR 1,740 total
includes taxes & fees
14 Feb - 15 Feb
Charming Cottage in the Heart of the Shawangunks
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
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 1,453 total
includes taxes & fees
25 Feb - 26 Feb
Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly
19'Heated SwimSpa | Lake | Snow | Hikes | Firepit
Backyard with 19' swim spa, Solo fire pit, Gazebo, Grill, and Sting lights

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

The price is SAR 559
SAR 2,147 total
includes taxes & fees
18 Feb - 19 Feb
19'Heated SwimSpa | Lake | Snow | Hikes | Firepit
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)
"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!

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
Ariel view of the property during sunset in winter

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 SAR 1,496
SAR 4,980 total
includes taxes & fees
18 Feb - 19 Feb
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 SAR 675
SAR 1,136 total
includes taxes & fees
19 Feb - 20 Feb
Hello Small Stone
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
14 Feb - 15 Feb
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
Autumn Foliage - Private Patio View

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 SAR 630
SAR 919 total
includes taxes & fees
17 Feb - 18 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Living room

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 SAR 598
SAR 1,210 total
includes taxes & fees
24 Feb - 25 Feb
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Exterior

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

9.6 out of 10, Exceptional, (38)
"The whole family had a great time! We would love to come back!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
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.