Pet-friendly holiday rentals in Middletown

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.

Serene Private Home • Light-Filled • Hot Tub •Deck

Spacious 3,600 sq ft home designed for comfort and ease in upstate New York 🌿 Light-filled rooms, open flow, and a hot tub + deck create a calm, elevated stay ✨ An open layout with multiple living areas makes it easy to gather while still having space to relax and unwind & enjoy throughout. The space functions as a self-contained part of a larger property, offering privacy and independence without feeling segmented. A comfortable base near farms, villages, dining, and outdoor activities.

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!

Enchanting River A-Frame|Fire Pit| Magical Forest

Escape to our Magical Riverside A-Frame on 4 secluded acres. Swim in the enchanting river, grill dinner under the trees, and gather by the fire pit beneath twinkling string lights & a sky scattered with endless stars. Watch deer, eagles & fireflies as you unwind in this cozy 2BR cabin. Perfect for couples, nature lovers, and anyone craving a peaceful retreat. Minutes from scenic hikes & Delaware River adventures connecting deep with nature - leave feeling like you stepped out of a storybook.

Victorian At Orange Square Entire Home

Immediately Feel Welcome As You Walk On To The Pillared Front Porch With Its Cushioned Deck Furniture. Enter The Welcoming Foyer And Feel The Comfort Of Home. Sink Deep In The Stuffed Couches In Front Of The Remote Controlled Gas Fireplace. Enjoy Your Favorite Book Or The Smart TV Entertainment Center. If Inclined Cook A Meal In The Modern Kitchen And Dine In The Elegant Dining Room With A Wood Burning Fireplace. Fire pit in back yard that can be viewed from the 6 person 104 degree Jacuzzi.

Modern BoHo 3BR Cottage Near by Hiking, Winery

Our newly modern bohemian cottage (aka Green House!) is perfect for your next weekend getaway or a new WFH locale. Decompress from city stress in this calm, serenely appointed private home. Close to attractions but far enough away to escape, you'll never want to leave. NYC: 79 mi. Hunter Mountain Ski Resort: 60 mi. Pine Bush - groceries/supplies: 7 mi. Middletown - shopping (Walmart, Target, Best Buy, Home Depot): 16 mi. Hiking trails: 7 mi. Horseback riding: 7 mi. Sky diving: 15 mi.

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!

Spacious 6BR Villa | Serene Scenic Mountain Escape

Escape to this spacious 6BR villa, a serene mountain retreat with scenic views. This peaceful getaway is perfect for families and groups. Located approximately 1 hour from New York city, it offers comfortable interiors, a well-equipped home, and ample outdoor space. Explore nearby hiking trails and relax in a tranquil setting just minutes from local attractions. Unwind and experience nature in every direction. Your peaceful mountain escape awaits—BOOK NOW FOR A SERENE GETAWAY!

Catskills Barn Retreat w/Fireplace & 9 Acres

Escape to this architecturally striking Catskills barn set on 9 private acres. Designed for gathering, the soaring living room features a massive stone fireplace, dramatic spiral staircase, and cozy seating for long nights in. Perfect for birthdays, friend weekends, and family getaways, with private hiking trails, fire pit evenings, and playful nooks like the bright silo lounge and hanging chair comfortably sleeping 12 people across 4 bedrooms — all just 90 minutes from NYC.

Your Summer Escape - Cozy Forest with Deck & Views

Welcome to our peaceful sanctuary, tucked away in nature's embrace! This delightful home fuses modern amenities with the beauty of the wild, ideally located near a vibrant forest filled with towering trees. Outside, nature’s wonders await. Step onto the expansive deck, where cozy seating invites you to relax and take in the mesmerizing forest views. You might catch sight of birds flitting through the canopy or glimpse wildlife roaming freely in their natural habitat.

Bright Farm House- Tranquil setting

Secluded 3-bedroom newly renovated late 1800 Farm house on a 50 acre working farm nestled in the Hudson Valley. Only 60 miles from NYC and close to everything the Hudson Valley has to offer. Many farms with seasonal apple picking and pumpkin picking ,West point , Woodbury Commons Premium outlets ,Resorts Casino. Tons of great local breweries ,Hudson Valley Wine Trail .. LegoLand Theme park is just 5 minutes away

Gorgeous Chalet with Lots of Room!

Unwind in style in our newly remodeled A-frame chalet! This cozy retreat comfortably sleeps 4 adults with room for more! Enjoy evenings around the fire pit in the backyard—everything you need is provided for a relaxing night under the stars. Inside, a spacious, custom-built dining table seats eight, offering plenty of room to dine, play games, and simply enjoy each other's company.