Holiday rentals with outdoor seating in Olive

Catskills Getaway w/AC on 3 Acres near Woodstock

You have the whole house and three acres to enjoy. The two bedrooms are upstairs, with skylights and a bright, airy feel to them. The wood burning stove is an awesome way to make things cozy. There's also a firepit and grill you're welcome to use. Guests have complete access to the home and three-acre property. The garage on the property is inaccessible by guests. We're available to contact anytime. Hike, ski, swim, bike, do yoga, or whatever comes to mind— all is possible in the Catskills. The Ashokan reservoir bike/walk path is a few miles down the road. Not far the other way is Marty's Mercantile for coffee, lunch, and basic supplies. There's plenty of parking in the driveway. Don't expect to Uber while up here. Walk, bike, or ride a horse instead. :) There's plenty of parking in the driveway.

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

The Lily Cottage Guesthouse

Tuck up in a thoughtfully renovated 1950s one bedroom cottage, perfect for a solo or a couples Catskill getaway! Situated in a quiet hamlet, nights in are lit by starlight and serenaded by peepers. Perfectly hemmed in by the Ashokan Reservoir, hiking, and the rail trail. The interior features a mix of vintage furnishings along with modern comforts. A 20 minute drive takes you to Rosendale, Kingston, or Woodstock for shops, breweries and excellent dining. Town of Olive Registration # STR-22-23

Catskills Mountain River Dream House

*Art-filled c. 1910 Cottage w/ wrap-around porch *Self-contained natural wonderland for grownups, kids, & dogs *Riverfront w/ amazing swimming hole: trout fishing, swimming, tubing on site *Huge back yard w/ meandering brook, seasonal cascade, classic tree swing, & surrounding woods *Speedminton court *Mature perennial butterfly gardens *Fire pit *Weber Gas Grill *Cedar hot outdoor rain shower nestled in side garden *Minutes walk to Ashokan Reservoir Rail Trail (run/bike/stroll); 2 adult bikes

Hudson Valley Botanical Garden Rental

Located in Upstate New York on the edge of our Botanical Garden in the Lower Hudson Valley the "Barnette" is for nature lovers. This newly built repurposed barn is perfect for relaxing, exploring nature, and getting away from it all. Nearby are lots of hiking, rail trails, and farms. We are within driving distance of the Mohonk Mountain House, Minnewaska, Catskill Mountains, and a 2 hour drive from Manhattan. For winter enthusiasts there’s places to snowshoe, ski, and hike 20-60 minutes away.

Cozy, Serene, Modern Cabin Escape

Escape to a cozy, modern log cabin nestled on 6 private, wooded acres. Designed for rest, reconnection, and comfort, this dog-friendly cabin offers total privacy with the convenience of being just minutes from town. Whether you’re planning a romantic weekend getaway, a peaceful work-from-home escape, or a nature-filled retreat, we invite you to slow down and unwind. You’ll feel worlds away from the noise, yet close to everything that makes the Hudson Valley special. IG:@griffithhousecabin

Stylish and Cozy Mountain Retreat

Private entrance into a stylish, cozy upstairs studio in artist's mid-century home near The Ashokan Reservoir. The Catskills are the destination for hiking, art, skiing, swimming or checking out the local food scene and breweries - all within minutes. Guests have the second floor to the home with no shared spaces with host. Outdoor seating with grill, barn with bocci and other yard games. King size bed, day bed with plush bedding. Spacious new bathroom with tiled shower and skylight.

Artful and Serene Woodstock Getaway

Please read description thoroughly before booking. Relax with a comfortable mix of rustic and elegant in this colorful studio with loft bedroom in the Catskill Mountains of NY. Midway between lovely towns, Woodstock and Phoenicia. Full kitchen and bath, closet, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. Not suitable for children or infants. No smoking or vaping. We use fragrance free laundry detergent.

The Ashokan Guest House

This newly renovated guest house is attached to a 120 year-old farmhouse which originally housed the workers building the Ashokan Reservoir. This quiet refuge sits on a lovely 3-acre lot in Catskill Park within .5 mile of Ashokan Reservoir. An outdoor adventure in our beautiful Catskill Mountains awaits any direction you go. This is the perfect location for couples or individuals looking for a retreat (it is not child-proofed). Near Kingston, Woodstock and Stone Ridge.

Relaxing Cottage in the Catskill Mountains

1000 sq ft. cottage located on a 7 acre partially wooded property in the Catskills. Two bedrooms (one queen, one full), one bath, open floor plan with vaulted ceilings and sliding glass doors opening to a deck in the back yard. Cook and eat on the deck with both gas and charcoal grills, plus large dining table with umbrella. Fire pit outside and wood burning stove inside for extra warmth and ambience. Equipped with a backup generator. Dogs considered, just ask.

Cook House | Modern Cottage w/ Hot Tub & Fireplace

Featured in Vogue, Curbed, and Remodelista, Cook House by Reset Club is a fully renovated modern cottage in the Catskills with cozy minimalist vibes and kitchen gear designed to inspire your inner chef. Enjoy cooking while records spin across the Sonos. Eat al fresco on the porch, then head to the hot tub. Or binge your favorite show on the projection screen at the foot of the bed. Great for couples or individuals looking to relax and enjoy nature.

Fenced & Salt Water Pool | Cozy Catskills Cottage

The perfect spot to unwind with family, friends, and pups. Spend the day hiking, visiting farms, or trying local restaurants, then come home to the yard for kid-and-dog frolicking, “Squirrel TV” through long windows. Soak in the claw-foot tub or the jetted spa tub, then gather by the fire with wine and board games. Swim and make s’mores in summer, watch snow fall in winter, and enjoy peaceful views in every season, relax, play, laugh, repeat.