Photo by Vincent Ramundo

Search Cottages in Middletown

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

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 AED 617
AED 896 total
includes taxes & fees
24 Jan - 25 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)
"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
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 AED 731
AED 2,968 total
includes taxes & fees
26 Jan - 27 Jan
Lakefront | 22 acres | HotTub | Game Room
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 AED 1,039
AED 2,040 total
includes taxes & fees
3 Feb - 4 Feb
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, (135)
"We had such an amazing time!! David is so kind, helpful, and very responsive. Answered any/all questions we had in a timely manner. We’re looking forward to returning!! "
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
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 AED 606
AED 1,136 total
includes taxes & fees
26 Jan - 27 Jan
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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!
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 AED 1,252
AED 2,167 total
includes taxes & fees
23 Feb - 24 Feb
Charming Cottage in the Heart of the Shawangunks
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 AED 771
AED 1,427 total
includes taxes & fees
24 Jan - 25 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 AED 367
AED 477 total
includes taxes & fees
31 Jan - 1 Feb
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)
"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
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 AED 361
AED 983 total
includes taxes & fees
13 Feb - 14 Feb
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
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.
Don't see what you're looking for?
See all available properties in Middletown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
Royal Garden Main Cabin
Bathroom

Royal Garden Main Cabin

9.6 out of 10, Exceptional, (4)
"ABSOLUTELY BEAUTIFUL!!! Its was a treat staying here. Its out in the country. Its called a cabin but its more of a house. The bedrooms were perfect and the beds were comfy. The property had a pond, and a fire pit. We seen 3 deer as we were pulling into the driveway. ABSOLUTELY RECOMMEND THIS RENTAL!!"
Royal Garden Main Cabin
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 AED 617
AED 896 total
includes taxes & fees
24 Jan - 25 Jan
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.