Fitness-friendly holiday rentals in Olive

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 🚐 Airstream included in your stay 🐶 Pet friendly* 💪 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 *Fees apply.

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!

Comfortable Woodstock Getaway

Our peaceful property is 5 minutes from the Town of Woodstock, 15 minutes to historic Kingston and Exit 19 of the NYS-Thruway, and 45 minutes to ski areas. The house is large and spacious with a fully equipped kitchen, plenty of lounge space, a sunlit expansive library with a large variety of old and new books, a home gym, and a backyard with a fire pit. Great for families with or without kids and weekend getaways with friends. Our goal is to offer an affordable experience for all our guests.

Sunset Mountain View Retreat · 11 min to Woodstock

Florentine is a sunset-facing, mountain-view retreat on 15 private acres, 11 min to Woodstock—quiet, solar-powered, and designed by architect Barry Price with loft-size windows and golden walnut floors. Cook and gather in the chef’s kitchen, work on 520 Mbps Wi-Fi, then unwind by the fireplace or screened porch as sunset settles over the mountains. Early check-in/late check-out when available. Minutes to Woodstock/Phoenicia cafés & trails; easy to Belleayre, Hunter & Windham. Permit #21N-224.

Chef's kitchen, seclusion, and breathtaking views

This is an incredible house for groups, spacious, flooded with light, andd spectacular views from almost every room. The main level is a massive open living room/ chef's kitchen/ dining/ fireplace on one level and a sweeping sunny deck. The home features 3 main bedrooms with ensuites, plus 2 other big bedrooms, a total of 5 bathrooms, and a yoga room with views. The perfect, central Catskill location gives you access to restaurants, farm stands, hiking, skiing, Phoenicia, Woodstock, and more!

+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.

Antique Uptown Charmer w/ Five-Star Modern Kitchen

The best of modern designed paired with authentic historic Kingston bones. The house features 3 full luxe baths, HUGE new chef's kitchen with endless work surfaces - 3 ovens, and baking equipment galore. 2 full floors (+basement) offer room to cook and play, flowing from the kitchen to the dining deck to the hot tub deck. This freshly restored home will be your base camp for adventures, but once you come you won’t want to leave!Quiet workspaces, printer, choose your vibe to get work done.

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

**Dates not available? Send us a message. We haven't opened most of our 2026 dates yet and many are open.** Secluded log home nestled in 5 acres of Catskill mountain forest, with 4 bedrooms & 3.5 baths (incl. basement with built-in full size bunks). Enjoy a sunroom, screened porch, pool+ brand new hot tub, projection screen home theater & a treehouse that resembles a floating pirate ship 30 feet up in the trees. Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

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.

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.