Holiday rentals with a pool in Olive

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

**Dates blocked? Send us a message. We haven't opened most of our 2026 calendar yet & many days are actually available.** 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

4Br Mountain Brook House on 130 acres w/ trails

Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

Contemporary Guesthouse with Views and Privacy

Secluded studio on 13 acres in Bearsville with views of meadows, mountains and woods. Stand-alone guest house with queen size sleeping loft, kitchenette, fully tiled bathroom, elliptical trainer, and all amenities. Wake up in the morning and enjoy the amazing views with your coffee, hike in the woods, or meditate at the waterfall. In season enjoy the completely private heated pool. End the day with s'mores around the fire pit. An ideal getaway from the city yet only three miles to Woodstock.

Cozy & Spacious Country Home - All Seasons

We welcome you to stay at our inviting home in the hamlet of High Falls. The two-story early 1900's era farmhouse is set on 12 private acres off a quiet country road in a lovely residential area. Grounds feature access to woods & pond + the canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with patio furniture, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.

Secluded Woodstock Retreat with Pool and Sauna

Stunning, tranquil mountainside retreat with exposed beams, saltwater swimming pool, sauna, fireplace, soaking tubs and rain shower. Situated on a 5-acre wooded hilltop a ten minute drive from Woodstock and close to miles of walking trails. Roast marshmallows on the fire pit, flip burgers on the top of the line charcoal grill, and enjoy one of the best stargazing spots around. Indoors, find a well equipped kitchen and cinema sized tv screen with Netflix/Apple TV. Convenient to ski slopes.

Private Catskills Cabin Retreat w/Hot Tub

7 min drive to Phoenicia 10 min drive to Belleayre 25 min drive to Hunter 35 min drive to Windham Renovated 1920’s cabin style home nestled on 4 acres in the Catskill Mountains. Easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, and swimming holes. A ton of outdoor space to enjoy in addition to our fully private seasonal pool (Late May-Sept). 6 person hot tub is available year round. Not for parties!! Please be mindful of our neighbors!

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..

Peace & Privacy - High Falls (hot tub & salt pool)

Enjoy the serenity of this contemporary home on six private acres central to all the Hudson Valley has to offer; just 20 min. from the NYS Thruway. Year-round hot tub, seasonal salt water pool, fireplace, gourmet kitchen, and large deck & patio w/ fire pit make this the ultimate getaway. Sports enthusiasts, shoppers, and diners will delight in how close we are to amazing Catskills attractions. New Paltz, Kingston, Mohonk Preserve and Minnewaska State Park are just 15 minutes away.

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.

Cozy Catskills Escape: Sauna, Animals, Mt Views

Make the most of winter’s final weeks and take a break upstate. Escape the city bustle for a cozy, restorative stay at Napping Horse Farm! The Bird's Nest is a light-filled retreat nestled on 30 secluded acres at the foot of Overlook Mountain. Perfect for couples, solo travelers, and small families seeking wellness, stillness, and a memorable experience with rescue farm animals. Nature, comfort, and deep calm just 2 hours from NYC.

Kapitans Cottage Private POOL Minutes to Kingston

Soak up summer at this cozy vintage Catskills retreat with an in-ground saltwater pool (mid-May–Sept). Just minutes to Kingston, High Falls, Stone Ridge- restaurants, shops & farmers markets, plus miles of hiking trails, rail trails & swimming holes across the Hudson Valley. 2BR, 1.5BA with private yard, stone deck, fire pit & BBQ. Pet-friendly, peaceful and perfect for couples, families or midweek escapes. Generator on-site.

Spacious Catskills Farmhouse on over 5 acres!

Spring into fun in the Catskill Mountains! Enjoy a hike at one of our local trails or nature preserves. Try your luck at the casino, spend a day at the indoor water park, or play a round of golf at one of the local courses. You will feel right at home in this charming & restored 5BR farmhouse. Located on 5+ acres near the great Catskills Forest Preserve, this is a great place for four-season recreation.