Fitness-friendly holiday rentals in Philipstown

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.

Entire Home (private pool), Event Friendly

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

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🐕

Spa Cabin with 2 Suites & Hot Tub

Welcome to Your Dream Retreat! Enjoy our custom-built cabin on a scenic 5-acre lot in the Mid Hudson. With 5 bedrooms, 3.5 baths, & curated amenities, this home blends comfort & elegance for an unforgettable stay. Whether soaking in the hot tub, strolling nearby trails, or gathering around the fire pit, our cabin is your perfect home away from home. We’re proud to be in the top 1% of Airbnb listings—earned through thoughtful touches, warm hospitality & a space guests love coming back to.

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

Escape just 2 hrs from NYC to 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

Creekfront Cabin Sauna & Hot Tub Hikers Hollow

Tucked away in the small town of Cuddebackville, you will find a wonderful rough cut cabin with all the comforts and amenities for a relaxing stay. The cabin is situated on 3+ acres on a quiet dead end road with very minimal car activity. Enjoy the wonderful nature that surrounds you, with the calming sound of the stream in the background. The interior of the cabin has been updated to ensure an exceptionally comfortable stay while still holding true to its original 1940's charm.

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

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

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.

Mid Century Mod 5-Bed, Pool OPEN!, Dogs Welcome

Experience the ultimate family vacation in this exquisite Kerhonkson retreat. This five-bedroom, three-bathroom home offers a blend of mid-century modern design and luxurious amenities. Enjoy a private, heated saltwater pool, a chef's kitchen, and a double-sided fireplace. The fully fenced backyard ensures a safe and enjoyable space for children and pets. Explore the beauty of the surrounding area and create lasting memories.

Villa Retreat: Yoga Studio, Theater, EV Charger

Multi-level forest villa retreat in the Gunks, perfect for wellness escapes, creative retreats, or group getaways. Enjoy a private yoga studio, 110" home theater, EV charger, handmade furnishings, Casper and Nectar premium mattresses, and inspiring original art. Surrounded by forest with decks, private nooks, and cozy lounges, this beautifully designed home blends boutique comfort with spacious indoor-outdoor flow.

Crystal Wave LakeHouse

Make some memories at this renovated, family-friendly Lakefront Oasis! Lake Frontage on 3 Sides of the Property! Views of the Lake from Almost Every Window! Included is an extra 600 sq ft cottage that has been completely renovated for your enjoyment with a pool table. Utilized as a gaming room & yoga studio!