House vacation rentals in Middletown
Find and book unique houses on Airbnb
Top-rated house rentals in Middletown
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middletown house rentals
House rentals with a pool
Home in New Paltz
4.98 out of 5 average rating, 468 reviewsmidcentury mod fireplace walk 2 hiking trl/village
Home in Woodstock
4.99 out of 5 average rating, 250 reviewsThe Woodstock Barn House - Sauna, Gym, Jacuzzi
Home in East Stroudsburg
4.99 out of 5 average rating, 195 reviewsSki | Hike | Hot Tub | Firepit I Sauna
Home in West Milford
4.98 out of 5 average rating, 132 reviewsOn The Rocks In The Hot Tub
Home in Stroudsburg
5 out of 5 average rating, 101 reviewsSimply Serene 4 acres Sauna/Spa/Golf/Pool & More
Home in Pound Ridge
5 out of 5 average rating, 148 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
Home in Newburgh
4.98 out of 5 average rating, 100 reviewsBeautiful riverfront mid-century house
Home in Narrowsburg
4.95 out of 5 average rating, 177 reviewsMid-Century Modern House with Fireplace & Hot-Tub
Weekly house rentals
Home in Newburgh
4.99 out of 5 average rating, 141 reviewsBalmville Mid-Century Gem & Work From Home Retreat
Home in Woodstock
4.92 out of 5 average rating, 130 reviewsSerene Retreat w/ Cedar Hot Tub & Fire Pit
Home in Catskill
4.97 out of 5 average rating, 179 reviewsModern Prefabricated Architectural Retreat
Home in Germantown
4.95 out of 5 average rating, 398 reviewsAirbnb Magazine Featured Gorgeous Swedish Barn
Home in Parksville
4.97 out of 5 average rating, 157 reviewsCooley Mountain House *Hot Tub*
Home in Accord
4.97 out of 5 average rating, 124 reviewsLittle Minka - Woodland Japanese Cabin.
Home in West Milford
4.96 out of 5 average rating, 114 reviewsThe Wine & Wilderness Hideaway [Cal King •1hr NYC]
Home in Greenwood Lake
4.96 out of 5 average rating, 236 reviewsStylish Lakeside Chalet with Hot Tub
Private house rentals
Home in Highland Falls
4.92 out of 5 average rating, 115 reviewsLuxury Home Near West Point
Home in Middletown
4.89 out of 5 average rating, 93 reviewsHudson Valley Log Cabin with Lake Access & View
Home in Otisville
4.83 out of 5 average rating, 12 reviews3BedRM Cozy home Otisville Middletown Deer Park
Home in Greenwood Lake
4.98 out of 5 average rating, 110 reviewsHoliday season with Lake View!
Home in Germantown
4.96 out of 5 average rating, 298 reviewsModern Country Cottage, Views, Trails, Fireplace!
Home in Livingston Manor
4.95 out of 5 average rating, 280 reviewsRiver view:
Home in Wurtsboro
4.84 out of 5 average rating, 86 reviewsCozy Rustic Farmhouse With Wood Stove
Home in Middletown
4.96 out of 5 average rating, 55 reviewsWawayanda Lodge - Port Jervis, Hudson River
Quick stats about house rentals in Middletown
Total rentals
10 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
180 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Orange County Fair Speedway, Coney Island, and IHOP
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Niagara Falls Vacation rentals
- Montreal Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Cape Cod Vacation rentals
- Beach house rentals New York
- Lakehouse rentals New York
- Townhouse rentals New York
- Guesthouse rentals New York
- House rentals New York
- Earth house rentals United States
- Guesthouse rentals United States
- Lighthouse rentals United States
- House rentals United States
- Townhouse rentals United States
- Townhouse rentals Manhattan
- House rentals Manhattan
- Guesthouse rentals Brooklyn
- House rentals Brooklyn
- Townhouse rentals Brooklyn
- Treehouse rentals New York
- Tiny house rentals New York
- House rentals New York
- Lakehouse rentals New York
- Townhouse rentals New York
- Guesthouse rentals New York
- Monthly Rentals Middletown
- Rentals with a washer and dryer Middletown
- House rentals Orange County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom