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.

Luxurious Cozy Mountain Retreat 2BR-2BA - Ski/Spa.

✨ Luxurious Cozy 2 Bed/2 Bath Main-Level Condo ✨ Just 2 minutes from Minerals Resort and only 400 meters to Mountain Creek slopes🎿, water park, golf courses and scenic trails. Unwind in plush beds, spa-like baths, or enjoy board games by the 4K TVs and cozy fireplace. Features 2 private decks, a fully stocked kitchen, and a workstation💻. Pet 🐶, toddler, and senior-friendly. Located just steps from assigned parking and one of the few units with NO SPIRAL STAIRS. Perfect for families or groups!

Entire Home, Private Indoor Pool

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.

Mountain View Retreat w/ Hot Tub, Theater, and Gym

Thoughtfully designed, this secluded retreat is nestled on 12 acres of picturesque land in Warwick, NY. The exquisite home offers the perfect blend of luxury and tranquility, making it an ideal getaway for families and friends. Highlights include: -Huge deck with mountain views -115" 4k projection theater w/ seating for 10, wet bar, & popcorn machine -Hot tub w/ seating for 7 -Gym w/ indoor endless lap pool, Peloton bike, and yoga equipment -Game room w/ billiards & Pac-man -Gourmet kitchen

Remote Waterfall Cabin at Swiftwater Acres

Deep in a lush oak forest, on the bank of Bushkill Creek sits this hidden oasis. This is simply THEE most private abode in the entire area. Situated just feet from the water, the falls can be seen and heard from every room within the cabin’s charming, rustic interior. This spectacular 45 acre parcel is set within a vast reserve of state land: an oasis within an oasis. Just 90 minutes from NYC, this is a truly sublime atmosphere, perfect for those seeking a rejuvenating and inspiring getaway.

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.

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Spacious 6BR Villa | Serene Scenic Mountain Escape

Escape to this spacious 6-bedroom mountain villa, a peaceful retreat perfect for families and groups. Just about 1 hour from New York City, enjoy beautiful scenic views, comfortable living spaces, a well-equipped home, and plenty of outdoor space. Explore nearby hiking trails and local attractions, or simply relax and enjoy the quiet surroundings. Whether you're planning a family getaway or a weekend with friends, it's the perfect place to unwind, reconnect, and make lasting memories.

Modern 3BR BoHo Retreat/Nearby Hiking, Wineries

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.

Creekfront Cabin Sauna & Hot Tub Hikers Hollow

Tucked away in the small town of Cuddebackville, you will find a wonderful rough cut cabin with all the comforts and amenities for a relaxing stay. The cabin is situated on 3+ acres on a quiet dead end road with very minimal car activity. Enjoy the wonderful nature that surrounds you, with the calming sound of the stream in the background. The interior of the cabin has been updated to ensure an exceptionally comfortable stay while still holding true to its original 1940's charm.

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.

Balmville Mid-Century Gem & Work From Home Retreat

Gather with friends and family or enjoy a work from home getaway in this mid century gem, located in the lovely hamlet of Balmville. This section of the Hudson River Valley is known for its well-maintained historic homes, river views, and vibrant culture. Enjoy dinner and cocktails in the city of Newburgh just 1.5 miles away, or cross the bridge to Beacon (just 5 miles away) and enjoy all Main Street has to offer. Hike Mount Beacon, Breakneck Ridge, and more.