
Holiday rentals in Middletown
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Middletown
Guests agree: these stays are highly rated for location, cleanliness and more.
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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 reviewsApt 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 reviewsGroovy 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 reviewsCozy 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 reviewsWelcome 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 reviewsMilkweed 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 reviewsQuiet 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 reviewsLuxurious 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 reviewsCozy 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
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- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- Bethel Woods Center for the Arts
- Bushkill Falls
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Delaware Water Gap National Recreation Area
- Ringwood State Park
- Promised Land State Park
- Resorts World Catskills
- Rockland Lake State Park
- Walkway Over the Hudson State Historic Park
- Riverside Park
- Van Cortlandt Park Golf Course
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- St. Nicholas Park
- Inwood Hill Park
- Great Falls Park
- Wawayanda State Park
- Sterling Forest State Park