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Compare 122 Cottages in Middletown with updated reviews, rates, and availability.

Exterior
Mountain View escape
10.0 out of 10, Exceptional, (24)
"We've stayed in a number of VRBOs and none have been as well-appointed and welcoming as this Mountain View Escape home. Privacy and space, while close to wonderful towns and places to explore. Highly recommend!"
Mountain View escape
Exterior
Historic Cornwall-On-Hudson Cottage w/ Deck!
10.0 out of 10, Exceptional, (8)
"This was our best experience with a VRBO. The posted photos are excellent but, yet the home still exceeded expectations. The hosts were friendly and welcoming. We felt right at home. Great location in Cornwall. We highly recommend and will be staying here again in the future!"
Historic Cornwall-On-Hudson Cottage w/ Deck!
Exterior
Cozy Catskills Cottage: Creekside Deck & Fire Pit
10.0 out of 10, Exceptional, (3)
Cozy Catskills Cottage: Creekside Deck & Fire Pit
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Property grounds
Cozy Cottage w/ Hot Tub! — Family Friendly
10.0 out of 10, Exceptional, (8)
"we had gr8 time with our family even though it rained enjoyed brook fire pit hot tub tramperlin a great place to go with family very freindly host good communication than you alex !!!!"
Cozy Cottage w/ Hot Tub! — Family Friendly
Pool
Cottage at Millpond Falls - A Romantic and Luxurious Escape
10.0 out of 10, Exceptional, (124)
"waterfall and cottage are perfect getaway from the real world. the owners are terrific hosts and provide a wide assortment of amenities"
Cottage at Millpond Falls - A Romantic and Luxurious Escape
Interior
Lakefront Property in the Heart of the Catskills!
10.0 out of 10, Exceptional, (31)
"We could not be more pleased. The cottage is lovely and well appointed. It was peaceful, restful and beautiful. We will be back to this exact location again. Loved it. The only slight downside is the comfort of the bed. But otherwise, perfect."
Lakefront Property in the Heart of the Catskills!
Fridge, microwave, oven, stovetop
A Quaint Escape!
10.0 out of 10, Exceptional, (1)
"My parents stayed here to celebrate their 50th wedding anniversary - they loved the property and location."
The price is $200
$348 total
includes taxes & fees
May 30 - May 31
A Quaint Escape!
Fireplace, books, music library, stereo
Lazy River Cottage on the Delaware River
10.0 out of 10, Exceptional, (119)
"The cottage was perfect! Everything about the cottage was just as it was described. The cottage was neat as a pin upon arrival, we got in at night and David had the light on and music playing for us. Would definitely recommend the Cottage to others as the perfect weekend retreat."
Lazy River Cottage on the Delaware River
Property grounds
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
10.0 out of 10, Exceptional, (14)
"Everything is new and works well. Cottage was spotless and prepared well. Check in process, door locks, internet etc all perfect. Just a little too early in the season for leaves on trees, so didn't get the secluded feeling that we imagine would have been there just a couple of weeks later. Visited with our standard poodle - he loved it. Excellent dog park nearby."
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
Dining
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
Highchair, dining tables
NEW Spacious 5 bedrooms with Private Lake & Beach Access and Kayak!
10.0 out of 10, Exceptional, (2)
"We came up in the fall to meet friends halfway. The house was so clean and loved all the white sheets and towels. Mostly hardwood or tile in the house. Heat worked great. Huge bath that five kids all got in together and has a blast. Close to warnick which was cute. We did vineyards and farm activities. Lots of foliage. Close to the lake. Would go back for sure!"
NEW Spacious 5 bedrooms with Private Lake & Beach Access and Kayak!
Property grounds
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
10.0 out of 10, Exceptional, (2)
"We loved our weekend in Beacon. This small, charming rental was very clean and updated. The outdoor space made it feel bigger and you can’t beat the location. We highly recommend staying here and we woulld definitely come back!"
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
Property grounds
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
10.0 out of 10, Exceptional, (6)
"Great host! Awesome property. Very accommodating and a pleasure to deal with!"
The price is $108
$280 total
includes taxes & fees
May 23 - May 24
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Property grounds
Waterfront | 22 acres | Boats | HotTub | Rafting
10.0 out of 10, Exceptional, (20)
"This was everything we needed to get away from the stresses of life! We loved it and would love to go back!"
Waterfront | 22 acres | Boats | HotTub | Rafting
Exterior
Warm welcoming cozy cottage in the woods
9.8 out of 10, Exceptional, (15)
"We were so lucky to get this property, it is only 7 miles from the Bethel venue where we saw Rod Stewart in concert. The house had everything we needed, the master bed was so comfortable & high up! The nearby park was well worth the visit. We were able to attend a pancake breakfast at the nearby fire station. We spent most of our time in the porch area, nicely furnished & plenty of Hummingbirds at the feeder. We saw the deers daily. Such a great get-away for 2 Florida girls!"
Warm welcoming cozy cottage in the woods
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is $184
$264 total
includes taxes & fees
May 27 - May 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lake
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
9.8 out of 10, Exceptional, (91)
"My family was down for the Spartan race weekend. The property is in a perfect location for proximity to the mountain, as well as Beaches and playgrounds for the kids. It comfortably fit four adults and two kids, and the fenced yard was great for the dog. Michael is a thoughtful and responsive owner, and we are looking forward to staying again next time we are down."
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Property grounds
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (7)
"Thank you Ginny we had a lovely stay at your cottage. Was exactly as pictured! Was perfect for a night away. The only feedback we have is there was no body wash/soap or shampoo (but 3 bottles of conditioner) for the shower. And also in the main bedroom, the center support of the bed frame would shift even just getting into and out of bed. We were a little concerned it might give way but it held and mattress was comfortable. Besides those notes we would definitely recommend staying here!"
The price is $165
$316 total
includes taxes & fees
Jun 9 - Jun 10
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Property grounds
Charming Lakefront Cottage On Masten lake
9.8 out of 10, Exceptional, (33)
"This is an excellent place. Very clean, everything you need is supplied and easy access to a large lake. Within 20 minutes there is a lot of entertainment and food. I will be back. "
Charming Lakefront Cottage On Masten lake
Exterior
Charming lake community cottage with hot tub PET FRIENDLY
9.8 out of 10, Exceptional, (19)
"This was a perfect little cabin for me to spend two nights while I was in the area for a youth retreat. I was only there long enough to shower and sleep but it was very quiet and comfortable."
Charming lake community cottage with hot tub PET FRIENDLY
Don't see what you're looking for?
See all available properties in Middletown
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.

Other property types in Middletown

Property grounds
Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, (115)
"We spent a much needed relaxing weekend at this location. I can't say enough good things about this property. It was beautifully decorated, perfectly supplied, and very clean. We would rent this property again."
Lakefront Luxury on Greenwood Lake
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is $184
$264 total
includes taxes & fees
May 27 - May 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
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.

Middletown Cottages information

Number of reviews
575
Accommodation
122 Cottages
Lowest Price
$100
Highest Price
$200

Frequently asked questions

Why book your cottage in Middletown with Expedia?
Booking a cottage in Middletown is as easy as clicking on your travel dates and selecting your ideal place for outdoor recreation and relaxation. From ritzy retreats to budget-friendly stays and cottages that feature perks like free WiFi, Expedia has something for all tastes. As for awesome deals? We’ve got your back!
How can I find cheap cottages in Middletown?
The easiest way to find cheap cottages in Middletown is with Expedia’s convenient filter tool. Narrow your search results by star rating, amenities and budget to secure unbeatable deals in just a few clicks.
What is there to do in Middletown near my cottage?
Middletown has enough activities and experiences to keep you on the go for weeks (or months!), starting with Paramount Theatre. Castle Fun Center, Harness Racing Museum and Hall of Fame and Highland Lakes State Park are other renowned attractions. If you’re staying a while longer, Orange County Fair Speedway and Thomas Bull Memorial Park will add the finishing touches to your itinerary.

Recent reviews of Middletown hotels
Expedia verified reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

5/5 Excellent
"Excellent!! "
A verified traveler stayed at Sleep Inn & Suites Middletown - Goshen
Posted 12 hours ago
Sleep Inn & Suites Middletown - Goshen