
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

4Br Mountain Brook House on 130 acres w/ trails

Modern Lux 5-Bed, Pool Open! Dogs Welcome

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Wander Inn! Golf Sim, Hot Tub, Pools, Lake

Modern House with Private Pool, Hot-Tub, Fireplace

Stylish Woodstock Pool Home

Spacious Catskills Farmhouse w/ In-Ground Pool!

Peace & Privacy - High Falls (hot tub & salt pool)
Weekly house rentals

Unique Dutch Barn in the Hudson Valley

Welcome to Newburgh's Cozy Cove

Country Modern Home w/5-Acre land Relax Retreat

The Alexandria - Wurtsboro, NY

Cozy Delight

Ridgeview A-Frame: Stylish Kerhonkson Escape

The Montgomery Chalet

The First House
Private house rentals

little cozy house in the village

Renovated & Spacious 3BR Catskills Retreat

Retreat w/ Hot Tub, Gym, Cold Plunge, Office

Luxury Mountain Retreat with Panoramic Vista Views

Beautiful modern Catskills home

Boulder Tree House

Stylish river town escape with hot tub + fire pit

10-Acre Catskills Cabin | Pond, Firepit & Trails
Quick stats about house rentals in Middletown
Total rentals
10 properties
Nightly prices starting at
$54 CAD before taxes and fees
Total number of reviews
170 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Coney Island, Orange County Fair Speedway, and ShopRite of Wallkill
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- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- Bethel Woods Center for the Arts
- Bushkill Falls
- Delaware Water Gap National Recreation Area
- Minnewaska State Park Preserve
- Belleayre Mountain Ski Center
- The Kartrite Resort & Indoor Waterpark
- Thunder Ridge Ski Area
- Resorts World Catskills
- Promised Land State Park
- Ringwood State Park
- Hudson Highlands State Park
- Riverside Park
- Brotherhood, America's Oldest Winery
- Van Cortlandt Park Golf Course
- Walkway Over the Hudson State Historic Park
- Sterling Forest State Park
- St. Nicholas Park
- Rockland Lake State Park
- Inwood Hill Park
- Wawayanda State Park
- Villa Roma Ski Resort