Holiday rentals in Middletown

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Popular amenities for Middletown holiday rentals

Other great holiday rentals in Middletown

Top guest favourite
Flat in Montgomery
4.96 out of 5 average rating, 25 reviews

Apt 201 · Hudson Valley Luxury Apartment!

AmerigoRating, 5 stars5 days ago
Very spacious apartment. Very clean. Great location. The walking trails nearby were fun too.
Place to stay in Goshen
4.7 out of 5 average rating, 89 reviews

Groovy Digs for a unique stay on Murray Hill

JayleeRating, 5 stars1 month ago
Very glad I found Groovy Digs!! Loved the decor and how well put the together the host has the place. Great neighborhood with many things to do nearby. Would definitely recommend this place to others :) We hope to back again!
Home in Middletown
4.73 out of 5 average rating, 11 reviews

Cozy Delight

Sarah-JaneRating, 5 stars1 week ago
Sue was a super communicative and gracious host. Right down to ordering a French press for me since that is the way I prefer my coffee and having it delivered to the property. Super cute place, very comfortable, clean, comfy beds, and killer location.
Place to stay in Cuddebackville
4.78 out of 5 average rating, 180 reviews

Welcome to your twelve-sided getaway!

Rafael ArcesioRating, 5 stars2 weeks ago
The dodecagon house is located in a slightly remote area with good access. For those searching for nature, privacy, and outdoor activities. Many surrounding places for trekking. There is also at 20 minutes drive a small town Port Jarvis, with good restaurants and friendly people that we visited. If you have more time, you can go to Woodstock and return the same day. The house is pet friendly, there is no mobile phone signal but the house has internet and you can connect with the house network if you need. Shashin is in contact and responds promptly. We recommend it for nature lovers.
Top guest favourite
Tent in Livingston Manor
4.98 out of 5 average rating, 142 reviews

Milkweed Camp - Glamping in a Blueberry Field

MichelleRating, 5 stars5 days ago
Our stay at Milkweed camp was amazing! It was extremely serene and private. Alan provided everything you could think of for the stay. If you get a chance, I would peruse his pottery as well ! We stayed during a bit of a rainy day it was so nice falling asleep to the sound of the rain. If you’re looking for a little city get away - I would highly recommend!
Guest favourite
Home in Bloomingburg
4.93 out of 5 average rating, 61 reviews

Quiet Homey Rustic Retreat

KarenRating, 5 stars1 week ago
A lovely spot! Clean, well laid out and cozy. We loved the porch and kids had a blast w the ping pong and air hockey. Nice big kitchen that we enjoyed cooking in! Comfy beds, great water pressure in the showers and AC was a plus w the humid day. We stayed here for a family trip to Lego land and it was a great location!
Apartment in Vernon Township
5 out of 5 average rating, 5 reviews

Luxurious Cozy Mountain Retreat

MilagrosRating, 5 starstoday
Staying at this Airbnb was like stepping into a dream. From the moment I arrived, I was completely enveloped in peace, beauty, and the soothing sounds of nature. Tucked away in a serene, picturesque location, the property is surrounded by towering trees, birdsong, and fresh, crisp air that instantly melts away stress. The apartment/condo was spotless, beautifully designed, and cozy, with thoughtful touches throughout—from fresh coffee to comfy linens. I spent my day hiking at a nearby trail, bird watching, and simply relaxing on the porch with a good book. At night, the stars were unbelievable—no light pollution, just a sky full of wonder. The host was incredibly welcoming and responsive, providing everything I needed for a perfect stay. He even left a personalized note and some homemade treats, which made me feel very welcome. If you're looking to disconnect from the noise and reconnect with nature this is the place.
Home in Wurtsboro
4.86 out of 5 average rating, 109 reviews

Cozy Rustic Farmhouse With Wood Stove

RosauraRating, 5 stars1 month ago
This place was stunning, truly truly it looks better in person seriously, you just have to go. Very clean, very peaceful, great for pictures and very comfortable! Would 100% come back, my friends all agreed.

Quick stats about holiday rentals in Middletown

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹3,471 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

Destinations to explore

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