Cottage holiday rentals in Middletown

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Waterfall Paradise | Romantic Cottage | Firepit

<b>Escape to your private waterfall cottage!</b> The Cottage at Millpond Falls is perfect for couples seeking a romantic, five-star retreat just one hour from NYC. ✅ Comfy queen bed & super-clean luxury linens ✅Crackling fire pit by the falls ✅ Minutes to wineries, breweries & trails ✅ Nearby adventures: skiing, lake fun, orchards ❤️ SUPERHOST • Our most frequent review: "The best AirBnb experience we’ve ever had, can't wait to come back!" Book your dates while they’re open.

Cozy Lake Cottage

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets in any temps from inside or out, or coffee in the tree hut! Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes COMPLIMENTARY Firewood, NO CLEANING/PET FEES🐕

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.

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

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.

Cozy Cottage | Sauna + Stone Patio w/ Firepit

Escape to a serene cottage nestled on the Shawangunk Ridge. Unwind by the fireplace, soak in the private infrared sauna (with direct patio access), or relax outside on the natural stone terrace with a firepit and forest views. Crafted with care—from a 100-year-old reclaimed wood dining table to a curated “meaningful library” and hidden messages—this space invites calm, curiosity, and connection. Near trails, lakes, and local adventure. Thoughtful, cozy, and quietly unforgettable.

Bella Cottage w/Pool, BBQ - Catskill Getaway

Make lasting memories at this cozy Catskills retreat surrounded by private woods. Kids and adults alike will love spotting deer, enjoying peaceful outdoor time, and stargazing at night. Tucked away on a quiet private drive, the home offers a relaxing escape while staying just minutes from grocery stores, restaurants, and local essentials. With modern comforts and easy access to hiking, skiing, waterfalls, farms, and charming towns, it’s a perfect home base for your next getaway.

Cozy Lake Cottage

Cozy cottage in residential lake community, adjacent to historic fine dining restaurant. There is an approximate 150 yard walk down to the lake to enjoy the spectacular sunsets . Centrally located in the Hudson Valley near everything there is to experience. Located in our area Many Local Wineries ( Angry Orchard) Woodbury Commons Outlet Mall Historic Newburgh and Waterfront Culinary Institute of America US Military Academy New Paltz and Mohonk Mountain House

Upper Delaware River cottage

1930's cottage with spectacular views. Fully stocked and situated on a stretch of Upper Delaware river rapids near Narrowsburg, NY. Heat/AC system, fireplace, solo stove, barbecue and porch. There are 7 acres with river views and access . River is a couple hundred yards from cottage, lots of lawn, hammock, kayaking, lawn games, board games, hiking, fire pits, lots to do or just relax.

Catskills Modern Amber Lake Cottage

Featured in the NY Times, Amber Lake Cottage is nestled right on the bank of Amber Lake in Livingston Manor, NY. Just 2 hours from the bustle of your 9-5 in NYC, the home lets you catch your breath. Sleep in. Rowboat. Fix a drink by the fire. Dance to a record. Experiment with local produce in the chef's kitchen. See the stars above you. Hear quiet for the first time in months.

Lakefront House w/Private Dock, Fire Pit & Hot Tub

Cozy and recently renovated 1940s lakefront house right on the water. Enjoy views of the lake all around the house. Private dock, fire pit, and cedar hot tub. Under 2 hours from NYC, and 20 minutes to nearby shopping and restaurants as well as great hiking trails. High speed Internet and TV provided.