Holiday rentals with a hot tub in Olive

Cook House | Modern Cottage w/ Hot Tub & Fireplace

Featured in Vogue, Curbed, and Remodelista, Cook House 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. Hosted by The Reset Club, a member of 1% for the Planet.

Mt. Wonder: Cold Plunge, Sauna, Hot Tub and View

Welcome to the most splendid view in the Catskills. With a private outdoor spa. And just 10 min to Woodstock. This secluded cabin sits on 18 acres w/ private creek access & forest. Seeking a vacation w friends or a romantic escape? This is the place. Enjoy this rustic 2BD 1ba cabin year-round, incl the natural hot tub, sauna & cold plunge Amenities galore incl the spa, BBQ, firepit, games, wood stove & stocked kitchen. Peruse our books, be in nature or enjoy hikes & towns. This is the one.

Romantic Cabin with Sauna & Wood Fired Hot Tub

Voted GQ 18 Best Airbnbs with Hot Tubs. Under three hours from NYC and just 10 minutes off of Route 28, our rustic cabin is tucked away far from the rest of the world. Nestled in the woods perfectly situated on a hill the five acres of land make you feel completely removed from the city. The property includes a sweeping lawn, a deck for dining or star gazing, an outdoor fire pit, outdoor charcoal grill. Then there's the outdoor wood fired hot tub and sauna - the highlights! (#2022-STR-003)

Catskills Cabin Surrounded by Mountain Views+Spa!

Location is Everything! Our 3BR Catskills home is surrounded by breathtaking mountain views, and close to all including Woodstock Village, Phoenicia, Rivers, Hikes, Breweries, Ski Areas and more. Home is set high on a ridge overlooking nature from all angles on 3 private acres of land. Enormous brand new deck facing mountains with fire pit, grills. Perfect location for exploration. Tastefully decorated with brand new beds and furniture, fully stocked kitchen. Town of Olive STR-22-12.

Spruced Moose Lodge w. Hot Tub & open Pool to oct

*Pool Open Until Oct 21!* 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. We renovated the kitchen & master bed with new walls of windows in May - pics to come! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Modern Catskills Cabin with Hot Tub, Accord

Wake to forest views in a modern A-frame with 2 bedrooms, including a cozy loft. Hike nearby trails, soak in the cedar hot tub, or visit local breweries. In summer, barbecue or gather at the fire pit; in winter, warm up by the wood stove on the 2-acre Catskills property. Note: Guests must be 13 or older, and all teenagers must be listed on the reservation. Pets are welcome with prior approval, agreement to pet rules, and payment of the pet fee. Please contact the host before booking.

Modern Woodland Getaway with Hot Tub and Fire Pit

Get away from it all in this brand new, centrally located escape! Located in a private setting surrounded by quiet forest, you will feel isolated from the world, yet only a half mile away from Rt. 209. In 10 minutes you can be hiking around Lake Minnewaska or strolling through the quaint town of Stone Ridge. Fine Dining in New Paltz and shopping in Kingston are only 25 minutes away. All that or relax at the house and enjoy the chef's kitchen, vaulted ceilings, hot tub and firepit.

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

Little Minka - Japanese House in the Woods

Little Minka. A serene Japanese folk house nestled on 10 acres of private woodland and streams. Embracing the Wabi-Sabi, Little Minka is unique, handcrafted using Japanese traditional carpentry joinery methods. Soaring ceilings, shoji, and tatami complete the interior. Outside there's a fire pit, open cooking area. We have a wood fired hot tub on request. We have Japanese bathroom products in partnership with sowakanyc that guests can experience.

Adorable Cottage w/ Hot Tub, Pond, and Rain Deck

Highlights: Cute-as-a-button secluded cottage with hot tub, pond, wood stove, and soaking tub. Very private, close to great hiking. Welcome to Fern Pond, a modern but enchanting cottage in quiet Kerhonkson. In the shadow of the Sundown Wild Forest, this sweet house offers a cozy base to explore Accord, Stone Ridge and the Ashokan Reservoir. Enjoy its privacy, remoteness, and romanticism, while soaking in the hot tub and/or cozying up by the fire.

Willow Treehouse - secluded, unique, romantic

The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109