Holiday houses 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.

%{current} / %{total}1 / 1
Top Guest favourite
An open artist loft features exposed wooden beams and a cozy seating area with a white sofa. A large area rug with vibrant patterns is situated on the wooden floor, while art pieces are displayed on the walls. A spacious bed is arranged at the far end, illuminated by natural light.
Guesthouse in Warwick
4.94 out of 5 average rating, 416 reviews

Rustic Loft Space with Distinctive Artistic Charm

Beautiful spacious and bright artist loft on the second floor of a newly renovated Warwick barn behind our 1893 Warwick Village home. More information The space We offer our furnished live and work artist loft on a daily or weekly basis. The loft : -is 400 sqf -is located on the second floor -has nicely designed bathroom -has a very comfortable queen size bed -has high speed internet access -is very tidy and clean The neighborhood: -one blocks from the NJ Transit bus to Manhattan. -great restaurants and cafés nearby This loft is wonderful is perfect for 2-4 visitors. You are in the middle of lovely village neighborhood, but get the comfort of a cozy retreat. Guests will have access to the entire SECOND FLOOR space. Situated in the lower Hudson Valley, the town of Warwick is just over an hour’s bus ride New York City. Explore its numerous orchards and wineries, head to the drive-in movie theater, or grab a bite from one of the village restaurants. The loft is just one block from the NJ Transit bus that leaves from Port Authority.

Guest favourite
The kitchenette features a compact design with white cabinets and a wooden countertop. A convection toaster oven, pots, and a sink are visible, along with various kitchenware including plates and glasses. A towel hangs nearby, providing convenience for guests.
Guest suite in Mountainville
4.94 out of 5 average rating, 150 reviews

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited. We live here with kids/dogs so you may hear us moving

Guest favourite
A welcoming living area displays a warm leather sofa and a glass coffee table. A stylish hammock chair hangs nearby, while a fireplace with a stone surround serves as a focal point. Natural light filters through sheer curtains, enhancing the cozy ambiance.
Cottage in Middletown
4.96 out of 5 average rating, 85 reviews

⌂ Backyard Porch ⌂ Cozy Getaway ⌂ Catskills Hikes

• 1,200 sq. ft Charming Cottage • Beautiful decor, extra comfy beds • Central A/C • Screened-in porch overlooking private yard • 10 minutes to downtown area with bars & restaurants • Full kitchen + Propane Grill • Great for a retreat or to relax between adventures • Direct trains from NYC / Hoboken Renovated modern cottage is the perfect getaway - only 90 min from NYC! Close to all the beautiful sights Catskills / Hudson Valley has to offer. Families, explorers, business travelers will love it

Guest favourite
A two-story building is featured with large panoramic windows on the facade, allowing natural light to fill the interior. The first floor is occupied by an optical shop, while the surrounding area includes paved parking spaces and landscaped elements in front.
Place to stay in Warwick
4.95 out of 5 average rating, 352 reviews

Luxe Penthouse Studio MainSt Warwick, SteamShower!

Relax & Indulge in our Luxe Penthouse Studio with Elevator & Parking! Beautifully furnished on Main St. in Warwick- Walk to Everything! Panoramic windows with amazing views over Warwick. Spa steam shower with bluetooth speakers, luxury bath toiletries, Heavenly King bed with Egyptian cotton linens, 65 in. HD Smart TV, reclining leather theater seats, velvet loungers convert into sleepers, fully stocked designer kitchen with all appliances, Nespresso & Keurig, coffee, tea, bottled water included.

Top Guest favourite
Chalet in Pine Bush
4.97 out of 5 average rating, 118 reviews

Spacious A-Frame Getaway near Hiking and Wineries

Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

Guest favourite
Guest suite in Montgomery
4.94 out of 5 average rating, 543 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Guest favourite
Apartment in Goshen
4.8 out of 5 average rating, 282 reviews

Great apartment- closest to Legoland

Large studio apartment in an historic luxury setting. Guests have a private entrance with parking to a first floor, fun studio. Our property boasts a private tennis/pickleball court for guest use and is situated directly on the Heritage Trail, which is perfect for biking and jogging. Our home borders several hundred acres of scenic rural property, yet we are conveniently located in the charming, historic Village of Goshen - within walking distance to restaurants and the Trotting Horse Museum

Guest favourite
The exterior of the Victorian mansion features a vibrant yellow facade with intricate trim details. A spacious porch is adorned with potted plants, and green trees provide shade over the yard. Steps lead up to the entrance, inviting visitors to explore the interior.
Guest suite in Chester
4.95 out of 5 average rating, 365 reviews

Serene Victorian Guest Apartment with Clawfoot Tub

Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–6 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

Guest favourite
Cottage in Goshen
4.92 out of 5 average rating, 306 reviews

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

Guest favourite
Apartment in Newburgh
4.89 out of 5 average rating, 239 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Top Guest favourite
A red house is surrounded by vibrant autumn foliage, highlighting orange and yellow leaves on trees. A gravel path leads to the home, with two chairs visible in the outdoor seating area. Natural landscaping complements the serene wooded setting.
Home in Middletown
4.98 out of 5 average rating, 207 reviews

Peace and quiet. Comfy, private house to relax in

Quiet property,almost 8 acres, of beautiful wooded property . Set back from the road. Many trails, wineries and breweries nearby. Legoland is 20 minutes away and many antique shops within 30 minutes or so. We live in the other house on the property, so we are accessible. You can take a stroll on the path by the stream or sit on the spacious 35 x 10 foot deck and enjoy the natural setting of the property. Fire pit is now available. Enjoy the night air and gaze at the stars.

Guest favourite
A charming red farmhouse is showcased against a backdrop of blue skies with scattered clouds. The structure features numerous windows, allowing natural light to illuminate the interior. Lush greenery surrounds the building, enhancing its inviting appearance.
Home in Wurtsboro
4.88 out of 5 average rating, 140 reviews

Cozy Rustic Farmhouse With Wood Stove

Make yourself at home in this unique farmhouse just an hour and a half away from NYC! Located right on the Bashakill Wildlife Refuge. this is the perfect getaway near Neversink Unique Area, Minnewaska State Park, Sam's Point, Legoland, and more! Enjoy the flicker of a wood-burning stove, make a BBQ feast on the outdoor deck, or admire the stars on a clear, dark night while sitting around the campfire. Good for couples, friends, or families–just no pets, please!

Popular amenities for Middletown holiday rentals

When is the best time to visit Middletown?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$124 AUD$111 AUD$101 AUD$87 AUD$105 AUD$142 AUD$142 AUD$142 AUD$142 AUD$136 AUD$132 AUD$145 AUD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

Frequently Asked Questions

  • Where should I stay in Middletown?

    Make yourself at home in Middletown by choosing from our most frequently booked neighborhoods. We have over 140 vacation rentals in Washington Heights, and over 140 vacation rentals in Middletown.

  • Are there vacation rentals with a dedicated workspace in Middletown?

    Yes! Work meets play with ease at over 30 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 wifi?

    Absolutely! We offer over 20 apartment rentals with wifi 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.

  • What are the most popular amenities for Apartment Rentals in Middletown?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Middletown

  • Total holiday rentals

    Explore 40 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at $56 AUD per night before taxes and fees

  • Verified guest reviews

    Over 540 verified reviews to help you choose

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Middletown holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Middletown rentals

  • 4.6 Average rating

    Middletown stays receive an average rating of 4.6 out of 5 from guests

  1. Airbnb
  2. United States
  3. New York
  4. Orange County
  5. Middletown