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Cottages in Middletown

Our top choices for Middletown cottages

Creek side cottage with awesome porch and fire pit

10.0 out of 10, Exceptional, (62)
"The home was so cute, clean and conveniently located. It was well stocked and the owners thought of everything to make it a home away from home. The driveway was a little challenging but it was a great place. Highly recommend!"
$215 nightly
The price is $228
Aug 24 - Aug 25
Total with taxes and fees
Creek side cottage with awesome porch and fire pit

Sleeps 8! Foosball+Arcade, Private Courtyard, Parking, Washer+Dryer. Great home!

9.6 out of 10, Exceptional, (11)
"Great house"
$293 nightly
The price is $323
Aug 25 - Aug 26
Total with taxes and fees
Sleeps 8! Foosball+Arcade, Private Courtyard, Parking, Washer+Dryer. Great home!

Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

10.0 out of 10, Exceptional, (120)
"This was a great overnight in a cute spot that we have seen along the higheay for years. Glad our fanily was finally able to check it out!"
$419 nightly
The price is $463
Sep 3 - Sep 4
Total with taxes and fees
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

Stone Cottage at Roundtop Estate couples Retreat

10.0 out of 10, Exceptional, (4)
"This property is pretty secluded and quiet. The pool and hot tub were a super plus. The pool cottage was very charming for my wife and myself. I wouldn't go with friends or children. The space is small but just right for a romantic getaway. The stringlights at dark, eating our late night snack on the patio, made for a very enchanting evening. The walking trails were nice also. We enjoyed it very much. "
$511 nightly
The price is $536
Sep 2 - Sep 3
Total with taxes and fees
Stone Cottage at Roundtop Estate couples Retreat
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