Cottage holiday rentals in Monticello

Driftwood Cottage on Welcome Lake-peaceful retreat

This gem of a vacation rental is perfectly situated on a private lake. Recently renovated, the main level features an open concept living area, with a cozy fireplace for chilly evenings, upgraded kitchen, a master bedroom with a luxurious en-suite bathroom. A charming loft serves as a cozy relaxation spot or additional sleeping area. Each room offers a spectacular lake view. Two full bathrooms ensures everyone has space to unwind. Outdoor includes a hot tub, perfect for relaxation by the lake.

The Schoolhouse at Kenoza Lake

The Schoolhouse at Kenoza Lake. This late 1800's renovated schoolhouse is the perfect getaway. Only a 2 hour drive from NYC. Old world charm with modern finishes. House features one bedroom plus a sleeping loft, a total of 3 beds plus a bunk bed, claw foot tub, cast iron wood stove, dinner barn, sleeping loft, vegetable garden, outdoor fire pit with bistro lights and Adirondack chairs. 10-20 min driving distance to all of Sullivan County's culinary offerings. 7 min drive to grocery store.

Luxury Historic School House Cottage

Step into history inside our freshly renovated 1800s school house home. Relax and take it easy on the expansive front porch, with sweeping views of rural farmland and a historic cemetery next door. Sit by the fire and enjoy a book or beverage with friends and family and cook a nice farmhouse meal. This unique and tranquil getaway won't disappoint. And it's just 4 minutes from Narrowsburg's Main Street. Swimming holes and hiking trails along the Delaware River are just a stone's throw away.

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 #33593

Catskills Cozy Retreat:Comfy Beds, Firepit, & More

Experience vintage charm at Jameson Cottage, a mid-century farmhouse-style home surrounded by nature. • Modern amenities and rustic wood finishes. • Gas grill and fire pit. • Two queen bedrooms, open living area, and full bathroom await. • Compact kitchen features beautiful cabinets and open shelves. • Relax in the living room or explore the backyard with its bountiful flora. • Embrace the amenities, unleash culinary creativity, and indulge in the luxury of a clawfoot tub.

Modern Upstate Escape with Outdoor Sauna

Newly renovated two bedroom, two bath cottage with four person barrel sauna at Swinging Bridge Reservoir, Sullivan County's largest motorboat lake. Updated amenities and mid-century and modern furniture provide a welcome respite from the city just 90 miles away. Take in the local scenery, catch a show at the Forestburgh Playhouse or stop into some of the local vineyards and restaurants. For a low key weekend, hang out by the fireplace playing some records and cooking a meal.

Cozy Cottage w/ Infrared Sauna

Escape to a serene, nature-inspired cottage nestled on the Shawangunk Ridge. Relax by the warm gas fireplace, gather around the handmade dining table crafted from 100-year-old reclaimed wood, or unwind in the private infrared sauna, accessible from the master bedroom. Explore nearby hiking trails, discover hidden messages throughout the space, and enjoy a curated "meaningful library." Perfect for relaxation, adventure, and meaningful moments with loved ones.

Lovely Cottage w/ Jacuzzi+Woodstove!

Nestled in the hamlet of Smallwood, only 2 hours from NYC, this newly renovated cottage is the perfect getaway from the city and an oasis surrounded by nature. This cottage is perfectly located for access to surrounding lakes and seasonal beaches, hiking trails as well as exploring and discovering the lovely Catskills region. The cottage features a wood stove, spacious deck, a fire pit as well as an all-season jacuzzi to enjoy day or night.

Dutchhillcottage, gem in the southern Catskills.

The Dutch Hill Cottage is a renovated, rustic chic design waiting for you and your friends or family to enjoy. Private, comfy & cozy country getaway with amazing views situated on 10 acres of rolling hills in the southern Cattskils, perched on a peak at the forests edge with expansive views all the way down to the Never Sink river with amazing suntset views from our huge deck. Plenty of ameneties and we welcome your petdog!