Family-friendly holiday rentals in Olive

4.99 out of 5 average rating, 177 reviews

A charming 1950s cottage exterior features a rustic wooden facade with a welcoming front door highlighted by a window and shutters. Lush greenery surrounds the entrance, with flowerbeds and decorative stones adding character. A gravel path leads to the main door, creating a cozy appeal.

Guesthouse in Olive

The Lily Cottage Guesthouse

Tuck up in a thoughtfully renovated 1950s one bedroom cottage, perfect for a solo or a couples Catskill getaway! Situated in a quiet hamlet, nights in are lit by starlight and serenaded by peepers. Perfectly hemmed in by the Ashokan Reservoir, hiking, and the rail trail. The interior features a mix of vintage furnishings along with modern comforts. A 20 minute drive takes you to Rosendale, Kingston, or Woodstock for shops, breweries and excellent dining. Town of Olive Registration # STR-22-23

KitchenFamilyAccuracy

4.93 out of 5 average rating, 269 reviews

A rustic cabin sits amid vibrant autumn foliage, surrounded by tall trees. A wooden deck wraps around the cabin, providing a spacious area for relaxation. A gravel path leads to the cabin, with a single chair positioned on the lush green lawn, inviting guests to enjoy the serene environment.

Home in Mount Tremper

Mt. Wonder: Big Cozy Cabin with Wow View

Welcome to Mt Wonder. With a wood burning hot tub, this secluded cabin sits on 18 acres with creek access, a vast forest & the greatest view in the county. Ten min to Woodstock. Seeking a vacation w friends or a romantic escape? Enjoy this rustic 2br 1ba cabin, cozy and spacious, with a unique magical feel. Mega amenities incl the tub, BBQ, wood stove & stocked kitchen. Peruse our books, vibe w the view, enjoy hikes & cute towns. Need more space? Try my cousin cabin: "Wonders Never Cease"

FamilyIndoor spacesTV

4.95 out of 5 average rating, 279 reviews

Cabin in Boiceville

Catskills Mountain River Dream House

*Art-filled c. 1910 Cottage w/ wrap-around porch *Self-contained natural wonderland for grownups, kids, & dogs *Riverfront w/ amazing swimming hole: trout fishing, swimming, tubing on site *Huge back yard w/ meandering brook, seasonal cascade, classic tree swing, & surrounding woods *Speedminton court *Mature perennial butterfly gardens *Fire pit *Weber Gas Grill *Cedar hot outdoor rain shower nestled in side garden *Minutes walk to Ashokan Reservoir Rail Trail (run/bike/stroll); 2 adult bikes

KitchenIndoor spacesWalkability

4.99 out of 5 average rating, 126 reviews

Home in Woodstock

Woodstock Catskills Retreat~Sweet, Private & Views

❤️A beauty in scenic nature with scenic rides to charming historic towns, Woodstock, Kingston, Phoenicia, Saugerties, Hunter & Belleayre ski and many outdoor adventures & dining options nearby. 🥾 😊 PinkyHouse, where friends and family gather for a lovely time and fond memories, welcomes you to its bright, sweet, peaceful, and private setting on 3.5 acres of green & forest with a brook and view of mountains. Enjoy your relaxing getaway here! 😊 🥾🚙⛰️ * No Pets & No-smoking xoxox anne 😊

FamilyKitchenCleanliness

The cabin's exterior features a dark wood facade surrounded by vibrant autumn foliage. A deck extends from the side, leading to a grassy area with three pink Adirondack chairs arranged for outdoor relaxation. A stone chimney rises from the roof, adding to the cozy appearance.

4.95 out of 5 average rating, 219 reviews

The Laurel Cabin

Tucked away in the serene Catskill mountains, this charming cabin has undergone a recent top-to-bottom renovation. Located just a short 5-min stroll from the vast expanse of the 30,000-acre Sundown Wild Forest, you'll discover endless trails, picturesque waterfalls, and abundant wildlife to explore. Additionally, within a mere 20-minute drive lies the stunning Minnewaska and Mohonk. We warmly welcome up to two well-behaved, non-aggressive dogs, although we regretfully cannot accommodate cats

FamilyIndoor spacesComfort

Guest suite in West Shokan

A small dining area is seen with a round wooden table and a patterned chair. A large window offers a view of the outdoors with trees and a rustic shed visible beyond. A piece of artwork is displayed on the wall, enhancing the cozy atmosphere.

4.94 out of 5 average rating, 247 reviews

Stylish and Cozy Mountain Retreat

Private entrance into a stylish, cozy upstairs studio in artist's mid-century home near The Ashokan Reservoir. The Catskills are the destination for hiking, art, skiing, swimming or checking out the local food scene and breweries - all within minutes. Guests have the second floor to the home with no shared spaces with host. Outdoor seating with grill, barn with bocci and other yard games. King size bed, day bed with plush bedding. Spacious new bathroom with tiled shower and skylight.

KitchenIndoor spacesAmenities

4.99 out of 5 average rating, 101 reviews

An inviting tent interior features a large, cozy bed adorned with textured bedding. A central wooden table holds decorative items and a lantern, while plush floor cushions are positioned nearby. The space is enhanced by light filtering through the tent fabric, casting playful shadows.

Tent in Kerhonkson

Catskills Glamp Oasis w. Breakfast by the Pond

Namahai Retreat is about communing with nature, trees, the elements, pond, fire, birds, flowers, and frogs, and most importantly, yourself. Situated on a 5-acre homestead in the heart of the Catskills Mountains, privately tucked in a Pine Grove, we hope you enjoy the serenity, nature, and magic found here. Botanically, it is a feast for the eyes. Bird watcher's paradise. Night sky full of stars. Your stay includes one complimentary breakfast, bonfire, and firewood for the tent stove.

FamilyIndoor spacesAccuracy

4.97 out of 5 average rating, 173 reviews

A spacious studio area features wooden beams above, with a large artwork displayed on the back wall. The floor is adorned with various rugs, and a kitchenette is visible, equipped with essential appliances. A chair is situated near a curtain-draped area, enhancing the room's functionality.

Home in Shokan

West Wing - a unique private space w/deck

This unique studio space with private entrance is a recent addition to our charming home, located on a quiet private road in the village of Shokan. Situated within minutes of the Ashokan Rail Trail, this bike and walking trail offers dramatic vistas of the Ashokan Reservoir. Woodstock & Phoencia with their stores, galleries and restaurants are only 15 minute drives . Local recreation includes hiking trails, kayaking and for those looking for relaxation there are renowned spas.

FamilyKitchenOutdoor spaces

Guesthouse in Olivebridge

A serene bedroom features a spacious bed adorned with decorative pillows and a soft throw. Nightstands with lamps are situated on either side. Natural light filters through two windows, complemented by light-colored curtains, creating a calm and inviting atmosphere.

4.95 out of 5 average rating, 209 reviews

The Ashokan Guest House

This newly renovated guest house is attached to a 120 year-old farmhouse which originally housed the workers building the Ashokan Reservoir. This quiet refuge sits on a lovely 3-acre lot in Catskill Park within .5 mile of Ashokan Reservoir. An outdoor adventure in our beautiful Catskill Mountains awaits any direction you go. This is the perfect location for couples or individuals looking for a retreat (it is not child-proofed). Near Kingston, Woodstock and Stone Ridge.

KitchenIndoor spacesHospitality

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

4.95 out of 5 average rating, 405 reviews

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.

Indoor spacesFamilyPets

4.94 out of 5 average rating, 596 reviews

A charming blue cabin is covered with a layer of fresh snow, creating a wintery scene. The front porch features a railing and steps leading to the snowy yard. Warm light glows from the windows, hinting at a cozy interior amidst the serene, wooded landscape.

Cabin in Olivebridge

Cozy Catskill Cabin on Acorn Hill

Enjoy a rustic respite from the city in this cozy cabin on 3.5 acres near the beautiful Ashokan reservoir and Catskill Park. Perfect for a relaxing weekend and as a hub for skiing and hiking. Cabin includes 1 bedroom and one bath, full kitchen, and living room with piano. This is a perfect get-away to relieve the stress of the city. Full amenity details are available in the listing. Town of Olive Registration # STR-22-19

Indoor spacesFamilyAccess

4.97 out of 5 average rating, 136 reviews

The entrance of a cottage is framed by lush greenery, showcasing a welcoming wooden porch and a dark door. Potted plants add a touch of charm to the inviting pathway, which leads through a grassy yard.

Cottage in Boiceville

Catskills Woodstock Design Retreat w/ hot tub

Little Willow is a newly-updated, three-bedroom cottage overlooking the mountains, designed as a cozy, handsomely-decorated launchpad for exploring the Catskills and Hudson River Valley. We now have a hot tub with mountain and sunset views! Check out our design feature in Domino Magazine. Town of Olive Permit: STR-22-13 Ulster Country Certificate of Authority: 10655

Indoor spacesFamilyHeating

Popular amenities for Olive family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 102 reviews

A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.

Home in Accord

Accord River House

KitchenFamilyAir conditioning

A sunlit living area features a modular sofa adorned with dark cushions, complemented by two vibrant orange tables. A freestanding black propane stove adds warmth, while light-colored wood accents and beams create a minimalistic aesthetic. A cozy rug lies beneath, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 332 reviews

Cook House, Modern Cottage with Hot Tub

FamilyKitchenCondition

4.96 out of 5 average rating, 108 reviews

Luxe modern A Frame, Hot tub and new heated pool

FamilyIndoor spacesHiking

5.0 out of 5 average rating, 148 reviews

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Indoor spacesKitchenGetting around

4.98 out of 5 average rating, 117 reviews

Home in Shokan

Historic Catskills farmhouse with sweeping views

KitchenFamilyBackyard

4.96 out of 5 average rating, 869 reviews

The Treehouse is nestled among trees, elevated above a tranquil pond. Its wooden structure features large windows that provide views into the surrounding greenery, while the natural landscape is reflected in the pond's surface. The setting offers a secluded feel contrasting with the nearby wooded area.

Treehouse in Willow

Willow Treehouse - secluded, unique, romantic

FamilyIndoor spacesBiking

4.99 out of 5 average rating, 190 reviews

Chalet in Olivebridge

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

FamilyKitchenHot tub

A modern house with a dark exterior is situated on a grassy lawn. The structure features large glass doors, providing views of the surrounding forest. A spacious deck with lounge chairs is visible, inviting relaxation in a serene woodland setting.

4.97 out of 5 average rating, 249 reviews

Modern Woodland Getaway with Hot Tub and Fire Pit

Indoor spacesFamilyHot tub

Family- and pet-friendly home rentals

A charming cabin stands surrounded by trees, illuminated by soft string lights. A fire pit with glowing embers is positioned in front, with a charcoal grill nearby. The cabin features large windows, allowing for views of the serene wooded landscape.

4.96 out of 5 average rating, 641 reviews

Cozy Cabin | Fire pit + Hiking + Pets Welcome

Indoor spacesKitchenValue

4.96 out of 5 average rating, 102 reviews

A spacious bedroom features modern furnishings, with a cozy bed dressed in white linens and a green throw. The calming view of a creek and forest can be seen through the window. An outdoor scene shows two individuals wading in the water amidst smooth rocks.

Cottage in Olive

PerchCottages #13: Creek access + Sauna + Mt views

FamilyIndoor spacesComfort

4.96 out of 5 average rating, 270 reviews

Cabin in Stone Ridge

6 Private, Serene Acres, Firepit, Screened Porch

KitchenIndoor spacesParking

A modern kitchen features sleek white cabinetry and stainless steel appliances, including a gas stove and refrigerator. A black island is enhanced by a minimalist pendant light above, while natural light floods in through large windows, illuminating a simple green plant centerpiece.

4.97 out of 5 average rating, 187 reviews

ENTER HOME - Minimalistic style warm & inviting

KitchenIndoor spacesBiking

The cabin features a rustic cedar shake exterior with a distinctive red front door. A spacious deck surrounds the entrance, providing a welcoming space. Vibrant autumn foliage frames the cabin, enhancing its natural setting within the forest.

4.97 out of 5 average rating, 180 reviews

Lovely Cabin w/Piano No Car Needed Best Hiking

FamilyKitchenHiking

The A-frame cabin is surrounded by lush greenery, featuring a sloped black exterior and large windows. A wooden deck is visible, equipped with two Adirondack chairs. Soft landscape lighting enhances the entrance, while the tranquil wooded setting provides a serene atmosphere.

4.95 out of 5 average rating, 115 reviews

Black A-Frame: Catskills Cabin

KitchenFamilyLong stay

4.96 out of 5 average rating, 169 reviews

Home in Stone Ridge

Contemporary Stone Ridge Retreat | 6 Private Acres

FamilyKitchenAmenities

4.93 out of 5 average rating, 866 reviews

Cabin in Woodstock

Byrdcliffe Artist Studio (27.1-1-70)

FamilyKitchenDecor

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 143 reviews

A sparkling heated pool is framed by natural surroundings, with a stand-alone guest house visible in the background. Lush trees create a serene atmosphere, enhancing the privacy of the outdoor space. Nearby, seating areas and open grass provide inviting spots for relaxation.

Cottage in Bearsville

Contemporary Guesthouse with Heated Pool

KitchenIndoor spacesGetting around

4.94 out of 5 average rating, 393 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

KitchenFamilySleep quality

Superhost

A spacious gazebo features a large hot tub alongside comfortable seating arrangements. The area is adorned with a patterned tile floor, and outdoor lighting hangs from the wooden beams. Lush greenery surrounds the gazebo, providing a serene atmosphere.

4.84 out of 5 average rating, 102 reviews

Country Getaway| Hot Tub| Pool | Fireplace | Games

Indoor spacesKitchenDecor

4.99 out of 5 average rating, 373 reviews

The interior space showcases exposed timber beams and a warm wood palette. A comfortable seating area is highlighted by a vibrant patchwork rug, while a staircase leads to the upper level. Shelving units display books, and a television is mounted on the wall.

Cottage in Woodstock

Grapevine Cottage

FamilyKitchenWi-Fi

4.96 out of 5 average rating, 306 reviews

A wooden lounge chair is positioned near a serene saltwater pool, surrounded by lush greenery. The pool's clear water reflects the inviting outdoor space, which is complemented by concrete paving and a manicured lawn.

Home in Cottekill

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

KitchenIndoor spacesNearby

4.98 out of 5 average rating, 544 reviews

Home in New Paltz

midcentury mod * POOL * walk out trail R2R/Mohonk

Indoor spacesKitchenAccuracy

4.89 out of 5 average rating, 189 reviews

An above-ground pool is surrounded by a wooden deck featuring lounge chairs. Lush greenery and trees provide a natural backdrop, while a fenced area with a swing set is visible in the distance, creating a serene outdoor space for relaxation.

Home in Woodstock

Shula | Farmhouse | Pool, Hot tub, Fire pit

FamilyKitchenBarbecue