
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.

Fully stocked creekside sauna retreat with privacy
Welcome to Bluskyz! (Blue Skies) Perfectly nestled between the charming village of New Paltz and the beauty of the Gunks and it’s surrounding countryside. Quiet culdesac road close to everything, ONE HOUR FROM THREE MOUNTAINS and within walking distance to a couple of real country gems. Top of a hill, this home has amazing privacy, and the quiet of being the last home on a dead end street. With a natural spring pool, pergoladining, sauna in the back yard, your private spa in the Gunks awaits

Entire Home (private pool), Event Friendly
This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Beaver Lake Escape
Welcome to Beaver Lake Escape! This one bedroom, one bathroom lakeview home has all of the amenities you will need for a relaxing vacation getaway! Come experience a warm & cozy environment with full access to the community beach where you can enjoy kayaking, swimming and fishing (catch & release). You'll also find great hiking in the Spring, Summer and Fall at the Neversink Gorge Unique Area and skiing/snow boarding in the winter at Holiday Mountain! Only a 25 minute drive to Bethel Woods!

Stunning Passive Solar Cabin on 135 acres & pond
Just the perfect cabin. This newly built, passive solar house has a wood-burning stove, incredible views and is drenched with light. The house is intimate yet connected to the outside, with total seclusion and every imaginable modern convenience! It’s an architect-designed marvel of concrete, glass and reclaimed wood that sits on 135 acres of field and forest with a lovely swimming pond and miles of hiking trails. The cabin sleeps up to 6 people in two bedrooms and a spacious sleeping loft.

The Little Green Farmhouse
Built in the mid 1800s, this 2,400 square foot. 2 story farmhouse is a comfortable country getaway with space for the whole family. Nestled on 2.5 acres, the house is perfectly positioned between the villages of Warwick and Sugar Loaf. There are 4 bedrooms on the 2nd floor with the ability to sleep 8 people. There are also 2 full bathrooms, a dining room, living room, office space, fully equipped kitchen, and a bonus space with a table to play board games, cards or puzzles.

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.

Historic Hudson Valley Farm House
This lovely historic farm house in the heart of the Hudson Valley is the perfect location for your next get away. The relaxation begins as you turn onto our long private drive, watch for wild turkey and deer. This is the perfect spot if you are coming to the area for a wedding, to visit West Point or LEGOLAND, go hiking, skiing or just to sample the local craft breweries and wineries. For art and music lovers Storm King Art Center, Dia Beacon and Bethel Woods are nearby.

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!

Cook House | Modern Cottage w/ Hot Tub & Fireplace
Featured in Vogue, Curbed, and Remodelista, Cook House by Reset Club is a fully renovated modern cottage in the Catskills with cozy minimalist vibes and kitchen gear designed to inspire your inner chef. Enjoy cooking while records spin across the Sonos. Eat al fresco on the porch, then head to the hot tub. Or binge your favorite show on the projection screen at the foot of the bed. Great for couples or individuals looking to relax and enjoy nature.

The Blue House on the Hill Catskills
Spectacular Mountain & Valley Views—Streamside. A beautifully renovated getaway located in the heart of the Catskill Mountains. Upon entering this gorgeous retreat, you will be instantly taken by the designer's attention to detail. Enjoy the open floor plan kitchen with soapstone countertops overlooking the amazing vaulted great room with spectacular views of the farm, valley, and surrounding mountains.

Architectural wonder in the woods
Unique experience, secluded. Enjoy a weekend or a few days eco-friendly retreat in an architectural, geometric masterpiece on 30 preserved acres just minutes from all that Rhinebeck and the Hudson Valley have to offer. The house is an open plan, and though it has zero bedrooms, it can sleep 4! Feel free to send us a message for any requests, we love hearing from people.

View House
Magnificent views from this fully renovated octagonal, mid-century glass house on secluded hilltop site. Views of and close access to Storm King Art Center, Schunnemunk State Park, Black Rock Forest. 60 mi from Manhattan, Town of Cornwall, NY. Perfect getaway from the city.
Popular amenities for Middletown house rentals
House rentals with a pool

Woodstock Family Home w/ Tree House + Heated Pool

midcentury mod * POOL * walk out trail 2 mohonk

TheGoshenGetawayPoolHotTubLegoLandArcade.

Private Retreat w/Pool, Hot Tub & Fire Pit, 6 BR

4Br Mountain Brook House on 130 acres w/ trails

Design Farmhouse w/ Pool + Firepit | Hudson Valley

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing

Cozy & Spacious Country Home - All Seasons
Weekly house rentals

Debruce Riverside Cabin directly on the Willowemoc

Cozy forest luxury cabin

Hilltop Hideaway Forest Villa on 13 acres!

Private Large Villa With Pool

Architect's Hudson Valley Home in the Woods

Accord River House

Cozy A-Frame with Deck and Fire Pit

Modern Luxe Lakefront Cabin
Private house rentals

Wellness Retreat w/ Hot Tub, Gym, Cold Plunge

4 bedroom house with pool (Kids & Dog Friendly)

Stone Sanctuary

The Montgomery Chalet

Rhinebeck Lakefront Private Retreat

The First House

Hemlock Cliffhouse: Secluded with Stunning Views

That 70s Camp
Quick stats about house rentals in Middletown

Total vacation rentals
Explore 10 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 50 verified reviews to help you choose

Wi-Fi availability
10 of Middletown vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middletown rentals

4.7 Average rating
Middletown stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Washington Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Bushkill Falls
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- Resorts World Catskills
- Delaware Water Gap National Recreation Area
- American Dream
- Mount Peter Ski Area
- Shawnee Mountain Ski Area
- Brotherhood, America's Oldest Winery
- Riverside Park
- Promised Land State Park
- Nickelodeon Universe
- Bear Mountain State Park
- Wawayanda State Park
- St. Nicholas Park
- Opus 40
- Paterson Great Falls National Historical Park
- Claws 'N' Paws
- Inwood Hill Park




