Family-friendly holiday rentals in Middletown

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited. We live here with kids/dogs so you may hear us moving

Luxe Penthouse Studio MainSt Warwick, SteamShower!

Relax & Indulge in our Luxe Penthouse Studio with Elevator & Parking! Beautifully furnished on Main St. in Warwick- Walk to Everything! Panoramic windows with amazing views over Warwick. Spa steam shower with bluetooth speakers, luxury bath toiletries, Heavenly King bed with Egyptian cotton linens, 65 in. HD Smart TV, reclining leather theater seats, velvet loungers convert into sleepers, fully stocked designer kitchen with all appliances, Nespresso & Keurig, coffee, tea, bottled water included.

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.

Fireplace—Chic & Renovated—Near Skiing & Tubing

Escape to The Original Bungalow, part of the @boutiquerentals_ collection–a newly renovated Scandi-chic retreat with a cozy gas fireplace & woodland backyard with a fire pit. Located just 2 hours from NYC in the Catskills (one of Travel+Leisure’s 50 Best Places), Smallwood is a destination in itself: walk along the lake, waterfall or hike the forest trails. Nearby are Holiday Mountain (skiing+tubing), Kartrite Waterpark, Bethel Woods+dining & shopping in Callicoon,Livingston Manor & Narrowsburg

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Forest Retreat in the Gunks | Cozy Mountain Escape

Set on the side of the Gunks and surrounded by quiet forest, this warm, cozy home is designed for guests who love nature and simple comfort. Just minutes from Minnewaska and Stony Kill Falls. Enjoy wood-burning stove, a handmade L-couch, premium queen mattresses, a forest-view kitchen stocked with high quality coffee, tea, and essentials. Thoughtful touches include incense, essential oils, Puracy toiletries, and a meaningful library. Two porches facing the woods create a warm, peaceful escape.

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

Great apartment- closest to Legoland

Large studio apartment in an historic luxury setting. Guests have a private entrance with parking to a first floor, fun studio. Our property boasts a private tennis/pickleball court for guest use and is situated directly on the Heritage Trail, which is perfect for biking and jogging. Our home borders several hundred acres of scenic rural property, yet we are conveniently located in the charming, historic Village of Goshen - within walking distance to restaurants and the Trotting Horse Museum

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!

Serene Victorian Guest Apartment with Clawfoot Tub

Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–6 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

Renovated 2 Bedroom Apartment in Heart of Village

Our newly renovated apartment is the lower level of a 1920 Victorian in the heart of the Village of Warwick. It boasts 650 sq ft of space with 2 bedrooms, and a full kitchen and bath. You can walk to beautiful shops, parks, and restaurants, or drive (free off-street parking) only minutes to ski, golf, hike, or enjoy our local orchards and wineries. There's even a doughnut shop across the street! All this with a huge backyard with it's own babbling creek! Welcome to 69 South St.