
Middletown vacation rentals
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Top-rated vacation rentals in Middletown
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Middletown vacation rentals
Other great vacation rentals in Middletown

Cozy mountain top home - views, 5acres & a gym.
What a perfect place to stay and unwind. The views are gorgeous, everything was comfortable and uncluttered and we felt perfectly at home. We actually both worked remotely for a few days, then took the last few for ourselves and everything worked fine (no internet issues being fairly remote). We cooked after shopping at Main Street and Pecks, ordered takeout from the Kaatskeller, and spent too much in the local shops. We love the area and now we have a new favorite location. Thanks for everything!

The Stonefire Cabin!
I booked this property as a kind of ad hoc writing retreat. It was the perfect location to complete what work I needed to do. A quick drive into Sparta for restaurants and supplies also made this a great location.

The Great Escape
Great place. House is lovely, clean and peaceful.

200 yds Minerals - great for hotel weddings
The place was great and just as pictured/described. Joann gave great instructions and was very responsive. We were only there for a short stay for a race, but it looked like a great area I would’ve loved to explore if we had more time. The only thing I didn’t care for was the requirement for to wash and dry all towels before leaving. Since I already paid a hefty cleaning fee that seemed like a bit much. And the washer/dryer is small so this took a couple of loads to get done.

Driftwood Cottage on Welcome Lake-peaceful retreat
This home was an absolutely beautiful gateway for an 3 anniversary weekend with my girlfriend. The house was spotless clean with everything you could need. Beautiful views from everywhere in the house. Amazing kitchen fully stocked and 2 perfect bathrooms makes for a very convenient stay. The property was so beautifully filled with so much nature and I could stare at the lake all day. Wonderful fishing and birds all day. Truly a beautiful place all around and made for a perfect weekend filled with great memories.

Perfect Vacation Home w/ Game Room Theater Hot Tub
We love the home. Amazing outdoor space. The children and adults enjoyed the game room. The home was close to everything only 10 minute drive to the local plaza. It was clean and looked just as expected

5 bedroom 7 bed Cottage Sauna, Lake, Hike & Winery
House was very well stocked, great location, great communication, recommended!

Sweet Home Poconos
We had a terrific time. It’s a lovely home- 20 min from Shawnee mountain and steps away from an indoor/outdoor pool facility (depends on weather), sledding hill and small skiing hill with ski lift. I would absolutely stay here again- and highly recommend for anyone with young kids looking to teach them to ski. Very very convenient. The hosts were available for questions and were friendly/flexible. Incredible customer service. We will be back!
Quick stats about vacation rentals in Middletown
Total rentals
40 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
550 reviews
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Middletown?
Yes! Work meets play with ease at over 20 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Middletown?
Experience the best of Middletown with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Middletown have wireless internet?
Absolutely! We offer over 10 apartment rentals with wireless internet in Middletown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middletown have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Middletown. Enjoy a tailored experience with all the comforts you desire.
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- Mountain Creek Resort
- Yankee Stadium
- MetLife Stadium
- St. Nicholas Park
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Bushkill Falls
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Thunder Ridge Ski Area
- Delaware Water Gap National Recreation Area
- Ringwood State Park
- Promised Land State Park
- Resorts World Catskills
- Rockland Lake State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Walkway Over the Hudson State Historic Park
- Riverside Park
- Sterling Forest State Park
- Inwood Hill Park
- Great Falls Park
- Van Cortlandt Park Golf Course
- Tallman Mountain State Park
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