Vacation rentals with a pool in Olive

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

Location · Value · Pets

Scenic River View Escape | New Paltz

Unwind in nature at this scenic New Paltz escape, located on a serene riverbank with spectacular views. Large porch and private backyard are perfect for relaxation and stargazing. Recently renovated, the house blends modern amenities with a tranquil atmosphere. Thoughtfully designed, it features a cozy fireplace, large smart TV, and fully equipped kitchen. Explore nearby hiking trails, waterfalls, and Minnewaska State Park, or relax in the hot tub. Ideal for couples, families, and remote workers

Value · Family · TV

Contemporary Guesthouse with Heated Pool

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.

Family · Value · Getting around

Comfortable & 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 and canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with furnished patio, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.

Location · Family · Hospitality

Woodstock Mountain Cottage w/ Swimming Pool

This romantic 2 bed cottage has large beamed ceilings, fully stocked kitchen, bathtub, mountain views, and hiking trails. We use strict cleaning protocols to ensure each stay is perfect and feels like home. The house is equipped with fast wifi and a ROKU Ultra for your tv needs! Located just 3 mins to the center of Woodstock. Swim in the pool, hike a trail, enjoy nature, grill or relax in the hammock. Pool is shared only with hosts & very private. No guests of guests allowed & no parties.

Value · Family · Shared spaces

Quiet Country Side Home With A Hot Tub/Pool

Olivebridge is a quiet and beautiful area! My home features an outdoor Hot Tub, Jacuzzi Jet Bathtub, High Speed Internet! So Many skiing/hiking areas nearby, Large Lawn to play a game of Horseshoes or sit by the fire pit and roast s’mores! All year round we have breathtaking views here in the Catskills. My home is only 20 minutes to the Town of WOODSTOCK! The upstairs of my home with all the amenities and property will be all yours during your stay! You have Access To Everything You Need!

Location · Value · Pool

midcentury mod * POOL * walk out trail R2R/Mohonk

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. IN GROUND SWIMMING POOL & HOT TUB short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk to an organic farm? A scenic mile to R2R trail to Mohonk, Water St. mkt & the Village of NP WHOLE PLACE IS YOURS HOUSE & PROPERTY POOL May 1 -Sept 23 HOT TUB YEAR ROUND

Value · Location · Condition

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..

Value · Location · EV charging

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.

Location · Value · Sleep quality

Secluded Woodstock Retreat -Heated Pool and Sauna

Stunning, tranquil mountainside retreat with exposed beams, heated saltwater swimming pool, sauna, fireplace, soaking tub and rain shower. Situated on a 5-acre wooded hilltop, a ten minute drive to Woodstock and close to miles of walking trails. Roast marshmallows on the fire pit, flip burgers on the 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.

Location · Family · Wifi

Luxe modern A Frame, Hot tub and new heated pool

Experience the luxury of this black double A-frame, finished to the highest standards and nestled in the woods for ultimate privacy. The main bedroom features a soaring ceiling and spa-like en-suite with walk-in shower, tub, bidet, double sink, and heated floors. The sunny second bedroom also has an en-suite. Enjoy a chef’s kitchen, double-sided fireplace, hot tub, and a new pool available June. Pets must be disclosed and approved prior to booking.

Value · Location · Quiet

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.

Value · Family · Pool