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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Featured Cottages in Middletown

Cozy Haven: A Romantic Retreat in our Tiny House!
Exterior

Cozy Haven: A Romantic Retreat in our Tiny House!

7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
The price is AU$460
includes taxes & fees
9 Oct - 10 Oct
Cozy Haven: A Romantic Retreat in our Tiny House!
Hello Small Stone
Exterior

Hello Small Stone

9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
The price is AU$664
includes taxes & fees
15 Oct - 16 Oct
Hello Small Stone
Creek Dips & Smores: Catskills Gem
House (3 Bedrooms) | Interior

Creek Dips & Smores: Catskills Gem

3.0 star property
The price is AU$677
includes taxes & fees
9 Oct - 10 Oct
Creek Dips & Smores: Catskills Gem
Hike & Fish: Outdoor Retreat Near Trails
House (1 Bedroom) | Interior

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
The price is AU$465
includes taxes & fees
9 Oct - 10 Oct
Hike & Fish: Outdoor Retreat Near Trails
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Exterior

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

10.0 out of 10, Exceptional, (1)
"The place was as described, quaint, clean, no issues with communication or check in"
The price is AU$328
includes taxes & fees
9 Oct - 10 Oct
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Cozy Cottage with Woodstock Scavenger Hunt
Terrace/patio

Cozy Cottage with Woodstock Scavenger Hunt

10.0 out of 10, Exceptional, (4)
"Great little cottage close to Bethel Woods."
The price is AU$426
includes taxes & fees
12 Oct - 13 Oct
Cozy Cottage with Woodstock Scavenger Hunt
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Exterior

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

9.4 out of 10, Exceptional, (12)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
The price is AU$412
includes taxes & fees
9 Oct - 10 Oct
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Exterior

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

9.4 out of 10, Exceptional, (11)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
The price is AU$453
includes taxes & fees
9 Oct - 10 Oct
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Terrace/patio

SwimSpa | Lake | Fish | Kayak | Hike | Firepit

9.6 out of 10, Exceptional, (8)
"Enjoyed our stay very much! Would highly recommend for someone seeking a nice quite get-away. Very nice Swim-spa for relaxation, many board games. We look forward to returning!"
The price is AU$1,104
includes taxes & fees
6 Nov - 7 Nov
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Children’s area

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

9.8 out of 10, Exceptional, (11)
"Wonderful cottage - lots of natural light - well equipped - great shower- comfortable beds- near Legoland - affordable- beautiful surroundings with great sunsets and sunrises - "
The price is AU$441
includes taxes & fees
16 Oct - 17 Oct
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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, (122)
"It has an incredible mountain and water view. "
The price is AU$472
includes taxes & fees
9 Oct - 10 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Outdoor dining

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

2.0 star property
8.8 out of 10, Excellent, (3)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
The price is AU$721
includes taxes & fees
15 Oct - 16 Oct
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Lakefront | Foliage | HotTub | GameRoom | Firepit
Outdoor dining

Lakefront | Foliage | HotTub | GameRoom | Firepit

10.0 out of 10, Exceptional, (33)
"It's a gem place that offers adventure for kids and relaxing for adults. Anyone could have awonderful time with family or friends. Definitel friends! "
The price is AU$1,293
includes taxes & fees
15 Oct - 16 Oct
Lakefront | Foliage | HotTub | GameRoom | Firepit
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
Terrace/patio

2 Lake Cabins | Pool+HotTub | Game Room | 23acs

10.0 out of 10, Exceptional, (2)
"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 AU$2,564
includes taxes & fees
6 Nov - 7 Nov
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
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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Top Middletown Hotel Reviews

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Found this hotel last year, it is super convenient for getting to the NY ren faire and has a Popeye's just up the driveway plus a whole shopping complex but you would never know when you are at the hotel. It is tucked all the way in the back and is nice & quiet. "
Jennifer 3-night trip
Posted 2 days ago
Hampton Inn Harriman Woodbury

Find out more about Middletown

Find out more about Middletown

Middletown Cottages information

Number of reviews
187
Accommodation
136 Cottages
Lowest Price
AU$328
Highest Price
AU$2,564

Frequently asked questions

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 Centre, 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.

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