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Vacation rentals in Middletown

Vacation rentals in Middletown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Sparrow’s Nest in Sparrow Bush, NY
SUPERHOSTEntire apartment · 10 guests · 7 beds · 2 baths
Sparrow’s Nest in Sparrow Bush, NY

Sparrow's Nest is embedded in evergreen and deciduous trees that make it a slice of heaven! Located 10 miles from town, it's a quiet get-away without being too remote from stores and sites. perfect for several couples, extended families. and friends' get-togethers. A full hot breakfast cooked by the hostess (in lower level) is offered at an additional price upon request. How convenient! Otherwise, help yourself to the breakfast items stored in the kitchen and freezer ~

What guests are saying:

“Janan is a true GEM. The space was great for my two good friends and I who were staying for a 7-day getaway from our current COVID lives. The home had everything we needed, and Janan was always there to provide a helping hand. We were comfortable, safe, clean and happy. All 3 of us were working M-F and had no issues with wifi, despite the numerous video calls. The fire pit was used daily and it was really easy to set up. Looking forward to stay again in the future. - tolu Janan was an exceptional host! Her place truly felt like a "home away from home" and gave us much-needed respite. The bedrooms, bathrooms, and common areas were clean and comfortable. The place is spacious, with lots of little nooks to explore (or work in)! The highlight of the space is the patio, which turns into an enchanting outdoor area at night with a fire pit and string lights. Janan does an amazing job maintaining the grounds - we took full advantage of the outdoor areas as weather permitted. Janan's warmth and hospitality made our stay an unforgettable one. THANK U JAN WE LOVE U AND CAN'T WAIT FOR THE WEDDING. XOXO - rachel”

Stargaze Lodge
SUPERHOSTEntire house · 8 guests · 3 beds · 2 baths
Stargaze Lodge

The house is brand new. It is set back off the road. its just minutes from the D&H Canal & Neversink river , 15 min from Bashakill vineyards oakland valley race track, also trains are available in either Port Jervis or Otisville & the same time to rt 17 or 84. 30 minutes to the Monticello casino or rt 97 Barryville also ski locations near both places , 40 minutes to warwick and chester & Milford Pa ,

What guests are saying:

“LOOK NO FURTHER THIS IS THE PLACE YOU WANT TO STAY AT ! GARY IS AN EXCEPTIONAL SUPER HOST AND GOES ABOVE AND BEYOND TO MAKE YOU STAY WONDERFUL. YOU WILL NEED NOTHING BUT THE CLOTHES YOU COME WITH BECAUSE HE HAS EVERYTHING YOU COULD THINK OF TO MAKE A GREAT GETAWAY TRIP. Me and my fiance were blown away once we arrived. The house is absolutely immaculate. Our dream home we have always wanted. Gary provides you with breakfast from eggs,bacon,bread, butter,waffles, Jimmy Dean breakfast sandwiches to coffee and tea ALL INCLUDED AT NO ADDITIONAL CHARGE. AND PLUS A COUPLE OF SURPRISES BUT I WON'T SAY A WORD. Also has some other goodies you can purchase for a low price . The best thing that we enjoyed was the huge tub in the master bedroom so relaxing. And the TV is HUGE AF big enough to enjoy movie night. If you enjoy grilling you'll enjoy the smoker/grill he has on the azing deck.Gary is so detailed with everything to make your stay remarkable and memorable. Anything you need help with he is there to answer that the drop of a dime. It was like having a tour guide he knows everything and every place to go . We will most definitely be back for sure and we will miss Frosty the cutest kitty who comes to visit. Thank you Soo much Gary for our special getaway during this pandemic .”

Mountain View House
SUPERHOSTEntire house · 6 guests · 3 beds · 2 baths
Mountain View House

Relax and take in the gently sloping woods of upstate New York from this newly renovated Mountain View House. Completely outfitted with a large kitchen, 3 remodeled, private bedrooms and 2 remodeled bathrooms, this listing is clean, cozy, and close to attractions like West Point Military Academy, Woodbury Outlets, Clearview Vineyard, horseback riding stables and farms with fresh, organic produce. Guests can also take a quick drive to the nearby towns of Port Jervis and Middletown.

What guests are saying:

“We really enjoyed this clean and spacious house. Our 14 month old was able to run around the place. The house is baby friendly and we felt comfortable letting him do so. Large size Smart TV, fully stock kitchen, excellent WI Fi signal and amazing pool- good recipe for great vacation Amazing, and very accommodating host. Hope to come back soon.”

Vacation rentals for every style

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  • Homes
  • Hotels
  • Unique stays

Popular amenities for Middletown vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Middletown

Sweet and spacious mountain view home w/fireplace!
SUPERHOSTEntire house
Sweet and spacious mountain view home w/fireplace!
Price:$171 / night
Beautiful home for rent
Entire house
Beautiful home for rent
Price:$214 / night
The Catskill Cube Tiny House.
SUPERHOSTTiny house
The Catskill Cube Tiny House.
Price:$123 / night
Private Waterfront home in 50 Acres of Woodland
Entire bungalow
Private Waterfront home in 50 Acres of Woodland
Price:$162 / night
Black Brook Schoolhouse,
Sullivan County NY
Entire cottage
Black Brook Schoolhouse, Sullivan County NY
Price:$164 / night
Delaware River Access, Pool, 90 miles from NYC
SUPERHOSTEntire cottage
Delaware River Access, Pool, 90 miles from NYC
Price:$139 / night
Creekside Lodge on the Mighty Delaware River
SUPERHOSTEntire guest suite
Creekside Lodge on the Mighty Delaware River
Price:$140 / night
The Goshen Slow Motion
SUPERHOSTEntire house
The Goshen Slow Motion
Price:$169 / night
Seclusion and romance, most popular airbnb around
SUPERHOSTEntire cottage
Seclusion and romance, most popular airbnb around
Price:$464 / night
On Golden Pond - Paradise! Very private.
SUPERHOSTEntire cabin
On Golden Pond - Paradise! Very private.
Price:$104 / night
R & R On The Knoll
SUPERHOSTEntire guest suite
R & R On The Knoll
Price:$87 / night
Glamping Dome
SUPERHOSTDome house
Glamping Dome
Price:$129 / night
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