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Search Middletown Cottage Rentals from CA $137

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Middletown Cottages

Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (52)
"This was such a lovely place to stay! Great location and beautiful setting. "
Mountain View escape
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, (109)
"Great place and host!"
The price is CA $232
CA $378 total
includes taxes & fees
May 13 - May 14
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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, (25)
"The cabin is in a great location for hiking and outdoor activities. We enjoyed the dog park and hiking trails close by. "
The price is CA $311
CA $612 total
includes taxes & fees
May 22 - May 23
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
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, (10)
"Wonderful stay, exactly as advertised, everything brand new and very cozy."
The price is CA $586
CA $1,093 total
includes taxes & fees
May 11 - May 12
Charming Cottage in the Heart of the Shawangunks
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 was great. It was nice to sit and relax by the small pond in the back."
The price is CA $248
CA $466 total
includes taxes & fees
May 14 - May 15
Hello Small Stone
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, (142)
"Everything was amazing. We spent Thanksgiving here. We definitely come back!"
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, (99)
"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
A romantic cottage and artist's retreat looking down over an enchanted lake
Property grounds

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
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, (144)
"Me and my boyfriend had an amazing time here. The property was very clean and well maintained. It’s a short drive to anywhere you want to go in Warwick! We will definitely be coming back to stay again :)"
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Historic 1800s Cornwall-On-Hudson Cottage!
Outdoor dining

Historic 1800s Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (22)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800s Cornwall-On-Hudson Cottage!
Charming Lakefront Cottage On Masten lake
Property grounds

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
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Miscellaneous

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

9.6 out of 10, Exceptional, (7)
"Great peaceful spot, close to a ton of outdoor activities. East check in and property was as advertised."
The price is CA $132
CA $267 total
includes taxes & fees
May 13 - May 14
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Miscellaneous

SwimSpa | Lake | Fish | Kayak | Hike | Firepit

10.0 out of 10, Exceptional, (1)
"We had the pleasure of staying at the Garden Cottage for a nice weekend getaway. Prior to arriving, our host, Jason sent detailed instructions, house policies and an amazing list of activities, attractions, restaurants and more so that we were able to have an idea of what we could do when we got here. Very helpful! Upon arrival, it was easy to get inside of this extremely clean, lovely abode. The space is warm and welcoming, decorated with much greenery in a very comforting environment. The...
The price is CA $155
CA $723 total
includes taxes & fees
May 4 - May 5
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Cozy Cottage with a Pond 2
1 bedroom, free WiFi

Cozy Cottage with a Pond 2

6.0 out of 10, (12)
"Was perfect place to stay with lots of hiking and waterfalls near by"
The price is CA $138
CA $201 total
includes taxes & fees
Jun 1 - Jun 2
Cozy Cottage with a Pond 2
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 $345
CA $700 total
includes taxes & fees
May 5 - May 6
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
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)
"Overall Great"
The price is CA $228
CA $425 total
includes taxes & fees
May 12 - May 13
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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 is perfectly located by the river. Breathe taking views"
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River
Charming Lake Community Cottage 2BR Retreat Near Mountain Creek
Fridge, microwave, oven, stovetop

Charming Lake Community Cottage 2BR Retreat Near Mountain Creek

10.0 out of 10, Exceptional, (1)
"We recently stayed here for the first time in order to visit with our new grandbaby nearby. It far exceeded our expectations - absolutely charming, two good sized bedrooms, working fireplace!, lovely living space, clean, clean, clean, parking spot, anything you forgot (toothbrush, etc.) provided, and a free snack basket! We'll be back. Communication with the host was immediate and helpful. Easy check-in and check-out. Ten stars."
Charming Lake Community Cottage 2BR Retreat Near Mountain Creek
Mountain House Escape - 1 Hour from NYC
Outdoor pool

Mountain House Escape - 1 Hour from NYC

10.0 out of 10, Exceptional, (7)
"Was a great location for a family gathering. The pool was great. The layout of the house was awesome."
Mountain House Escape - 1 Hour from NYC
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

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
5 bedrooms, desk, iron/ironing board, free WiFi

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (73)
"Celebrated my husbands 50th birthday and the property was perfect!"
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
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, (109)
"Great place and host!"
The price is CA $232
CA $378 total
includes taxes & fees
May 13 - May 14
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Cabin with Sauna & Firepit!
Outdoor dining

Cozy Cabin with Sauna & Firepit!

9.6 out of 10, Exceptional, (24)
"Excellent "
Cozy Cabin with Sauna & Firepit!
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.