Fitness-friendly holiday rentals in Olive

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.

Spacecraft Sanctuary x Stargate Self-Care Retreat

Nestled into a private forested locus in the charming hamlet of Halcottsville, NY is SPACECRAFTX1 SANCTUARY, a transformed single wide trailer with walls of glass sliders that showcase the ultimate designer, Mother Nature with her majestic mountain vistas, perennial x calming Japanese rock gardens. SPACECRAFTX1 STARGATE (separate structure) is a wellness studio for yoga, pilates, barre x meditation with an infrared sauna with chromotherapy for a “Design Your Own” self-care retreat experience.

The Woodland Valley Spa Cabin (20min to Woodstock)

Get away from it all and connect with nature at our luxurious cabin located right in the heart of the highly coveted Woodland Valley neighborhood of the Catskills. Conveniently located 9 min from downtown Phoenicia, 20 min from Woodstock for dining and culture, and 4 min from hiking trailheads. We painstakingly and lovingly designed the spa cabin, and if you come take advantage of all that it has to offer, we have no doubt you'll come away feeling rested, rejuvenated, and at one with nature!

+Unique+Chic+Catskills Charmer+Barn Retreat+

PEACE + NATURE + COMFORT De-stress and de-compress in the heart of the Hudson Valley farm to table food and music scene. Be rural without being remote. Experience a country getaway in an architecturally renovated barn with a huge stone fireplace and creature comforts. Get away from it all while still remaining close to services and amenities. Near Mohonk Mountain, Minnewaska, and Rail Trails. Minutes from the "Cultivated Wild" of Inness, Westwind Orchard, Arrowood Farms, and Stonehill's.

Gorgeous Waterfront w/ Hot Tub and Game Level

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to The Glass House! Here are a few things I think you’ll especially enjoy about the house. Highlights – You’ll love the: Peaceful waterfront setting – tucked away on the lake, yet just minutes to town Year-round hot tub – the perfect way to unwind after hiking, or exploring Family-perfect layout – two spacious levels with a game/media room and screened porch Kayaks & life vests – easy, safe access to the water for all ages

Dreamy A-Frame Cabin Hot-Tub | Games Room | Firept

Escape just 2 hrs from NYC > our dreamy mountain facing A-Frame cabin in the Catskills foothills. Close Hike's to some of the most beautiful trails, Swim Waterholes, or even climb waterfalls, and explore charming towns, farms & breweries/wineries by day. By night, grill on the overhanging deck, stargaze by the firepit, watch a movie in the cozy cinema/game room or soak in the hot tub under the stars. A magical retreat for couples, families & friends to relax, play, and reconnect

Hudson Valley Home

Hudson Valley Home - Stylish, clean and comfortable 4 bedroom home with expansive outdoor double-deck, fireplace, fire pit, BBQ, on a 3-acre property. Amazing Hiking, Apple Picking, Scenic Golf Courses, Vineyards, Inness (4min. away), Minnewaska State Park, Historic Kingston, Hip Woodstock, and New Paltz are all easily accessible from this conveniently located gem on a private road in Accord directly off the 209. Comfortable for a large group yet cozy for a couple.

4 BR Stunning Mountain Retreat w Hot Tub!

Experience the mountains in elevated style. This 4-bedroom retreat offers refined comfort, generous space, and serene mountain views—perfect for group gatherings or families seeking a high-end escape surrounded by nature. ⛰️ Private hot tub + fire pit 🐶 Pet friendly with pet fee 💪 Home gym ☕ Coffee/tea bar 🍽️ Fully functional kitchen 🛁 Plush linens + towels 🎲 Family amenities—pack & play, games, kid-friendly items 🎹 Finely tuned piano for music lovers

Sunset Mountain View Retreat · 11 min to Woodstock

Some views stop you. This is one of them. Florentine is a sunset-facing mountain view retreat on 15 private acres, 11 min to Woodstock—quiet, solar-powered, designed by architect Barry Price with loft-size windows and golden walnut floors. Cook in the chef's kitchen, work on 520 Mbps Wi-Fi, then unwind by the fireplace or screened porch at golden hour. Minutes to Woodstock/Phoenicia cafés & trails; easy to Belleayre, Hunter & Windham. Permit #21N-224.

Modern & Chic Log Home-Spectacular Mountain Views!

Welcome to Fox Ridge Chalet! Minimum age to book 21. A newly renovated, stylish log cabin nestled on 7 private acres above the village of Margaretville, in the heart of Catskills Park. Though the home is secluded, offering spectacular mountain views and total privacy, it’s just a three-minute drive to Margaretville’s restaurants, shops and galleries and under ten minutes to Belleayre Ski Resort as well many other local attractions.

Country Tiny Home w/ King Bed & Hot Tub 18 Acres

Escape to a romantic rustic tiny home nestled on 18 private acres in the Catskills, just 90 miles from NYC. This charming one-bedroom cottage is perfect for couples seeking quiet mornings, forest views, and cozy evenings under the stars. Sip coffee surrounded by nature, explore nearby trails, then return to your peaceful retreat to unwind and reconnect. A secluded hideaway with warm, five-star hospitality and true Hudson Valley charm.

Bright, Airy Home in Hudson w/ TONS of Character!

Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.