
Family-friendly holiday rentals in Ashokan Reservoir
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Ashokan Reservoir
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna
Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!
4.99 out of 5 average rating, 159 reviews
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
4.99 out of 5 average rating, 183 reviewsWoodstock 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.
4.94 out of 5 average rating, 398 reviews
The Woodstock Barn House - Sauna, Gym, Jacuzzi
19th Cent Hand-Hewn Dairy Barn. LOVE BIG GROUPS - if your #s exceed 10 we can accommodate. Pet Friendly Inquire for summer dates! IG: @woodstockbarnhouse 2 guest 1 night stays inquire for clean discount Travel & Leisure "Gorgeous Old Catskill Barn" House Beautiful "Best Upstate New York Weekend Destinations " Pool about May to midOct Hot Tub - all year Gym Sauna Fire Pit Projector Tv Pizza Ovens Cabana Kitchen 2 miles from center of town. *No checkin avail Tgiving, Xmas Day, Easter Sunday
4.99 out of 5 average rating, 279 reviews
Woodstock Hideaway
Escape to our cozy 3-bedroom, 2.5-bathroom home in the Catskill Mountains! Ideal for families, couples, or friends seeking a relaxing break. Unwind in front of the fireplace, whip up culinary delights in our chef's kitchen or grill out on the back deck. Relax and enjoy breathtaking mountain views by the firepit. Minutes away from hiking, swimming and ski slopes, offering endless outdoor adventures. Explore nearby Woodstock, known for its entertainment, shopping, and farm to table dining options.
4.98 out of 5 average rating, 119 reviews
Comfortable Woodstock Getaway
Our peaceful property is 5 minutes from the Town of Woodstock, 15 minutes to historic Kingston and Exit 19 of the NYS-Thruway, and 45 minutes to ski areas. The house is large and spacious with a fully equipped kitchen, plenty of lounge space, a sunlit expansive library with a large variety of old and new books, a home gym, and a backyard with a fire pit. Great for families with or without kids and weekend getaways with friends. Our goal is to offer an affordable experience for all our guests.
4.91 out of 5 average rating, 258 reviews
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 😊
4.96 out of 5 average rating, 133 reviews
Mt. Wonder: Big Cozy Cabin with Wow View
Welcome to Mt Wonder. With a wood burning hot tub, this quiet cabin perches on 18 acres with creek access, a vast forest & the greatest view in the county. 10 min to Woodstock. Seeking a vacation w friends or a romantic sojourn? Enjoy this rustic 2br 1ba cabin, cozy & spacious - a unique magical feel. Mega amenities incl the tub, wood stove & stocked kitchen. Peruse our books, vibe w the view, enjoy hikes & cute towns. Need more space? Try my cousin's cabin called "Wonders Never Cease"
4.93 out of 5 average rating, 277 reviews
Fall Farmhouse: Private, Firepit & Fireplace
Super private, pet-friendly 13 acre solar powered*, modern farmhouse 2 hours from NYC in Catskills. ✔ Large backyard w/ firepit ✔ Dogs allowed** ✔ 229Mbps wifi ✔ Screen-in porch w/ outdoor dining ✔ 65” Smart TV with Apple TV in living room ✔ 50” Smart TV with Apple TV in guest bed ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Back deck w/ BBQ grill ✔ Indoor fireplace ✔ Onsite parking 10 mins → Vernooy Falls 20 mins → Minnewaska State Park, Mohonk Preserve & Ashokan Rail Trail
4.98 out of 5 average rating, 191 reviews
Exquisite Chalet by Woodstock views, Ashokan water
Recently renovated 3 bedrooms, 2 baths chalet for 6, one mile from stunning Ashokan reservoir views, on private lane but in the heart of Catskills, 10 min from Woodstock, Kingston and exit 19 off hwy 87, with fireplace, wraparound deck, deer-proof yard, firepit, barbecue, veggie garden. Ideal for couples, families, friends. Minutes to ski, ice climbing, iceskating, swimming, hiking, rock climbing, tubing, fishing, scenic walks, biking trails, food markets & excellent restaurants.
4.98 out of 5 average rating, 350 reviews
Hudson Valley Hygge House~ comfort in the country!
Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!
4.95 out of 5 average rating, 374 reviews
Historic Catskills farmhouse with sweeping views
Welcome to Juniper Grove - your country home in the Catskills. This 4 bed 2 full/2 half bath farmhouse has stunning views of the Ashokan Reservoir to enjoy from the classic farmhouse front porch. Relax under the stars in the new hot tub on the back stone patio. Sitting on 40 private acres, you are held by Mother Nature at every turn. Inside find all the modern conveniences & comforts to support your stay.
4.98 out of 5 average rating, 122 reviewsPopular amenities for Ashokan Reservoir family-friendly rentals
Family-friendly home rentals with a hot tub

Catskills Woodstock Design Retreat w/ hot tub
4.97 out of 5 average rating, 140 reviews
Accord River House
4.99 out of 5 average rating, 107 reviews
Modern House with Mountain View @Getawind
4.96 out of 5 average rating, 233 reviews
Ye Little Wood | Cozy Forest Cottage with Hot Tub
5.0 out of 5 average rating, 253 reviews
Fall Escape | EV | Hot Tub
4.97 out of 5 average rating, 174 reviews
4Br Mountain Brook House on 130 acres w/ trails
4.88 out of 5 average rating, 222 reviews
Spruced Moose Lodge & Treehouse w/ New Hot Tub!
4.99 out of 5 average rating, 198 reviews
Willow Treehouse - secluded, unique, romantic
4.96 out of 5 average rating, 875 reviewsFamily- and pet-friendly home rentals

Black A-Frame: Catskills Cabin
4.95 out of 5 average rating, 120 reviews
Catskills Mountain River Dream House
4.95 out of 5 average rating, 282 reviews
Timberwall Ranger Station | Your Upstate Base Camp
4.99 out of 5 average rating, 220 reviews
Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star
5.0 out of 5 average rating, 463 reviews
Stunning 2-Bedroom A-Frame in the Woods with Sauna
4.98 out of 5 average rating, 297 reviews
Eclectic one-bedroom house
4.97 out of 5 average rating, 329 reviewsA Very Cozy House With a Very Big Yard
4.94 out of 5 average rating, 413 reviews
Away Upstate, a cozy retreat w/ Firepit
5.0 out of 5 average rating, 101 reviewsFamily-friendly home rentals with a pool

Chef’s Kitchen * Screened Porch * Near Woodstock
4.93 out of 5 average rating, 126 reviews
Comfortable & Spacious Country Home - All Seasons
4.98 out of 5 average rating, 123 reviews
Modern Getaway in Kingston - 1.5hr from NYC
4.91 out of 5 average rating, 117 reviews
Black Ridge Cottage: Pond, Cowboy Pool & Sauna
4.97 out of 5 average rating, 176 reviews
Entire Home, Private Indoor Pool
4.81 out of 5 average rating, 136 reviews
Grapevine Cottage
4.99 out of 5 average rating, 381 reviews
Sackett & Van Dam Guest House @ Little 9 Farm 1706
4.98 out of 5 average rating, 178 reviews
Woodstock Mountain Cottage & Pool - Swim & Hike
4.83 out of 5 average rating, 133 reviewsDestinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Mississauga Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Hunter Mountain
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Bethel Woods Center for the Arts
- Resorts World Catskills
- Windham Mountain
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Storm King Art Center
- Taconic State Park
- Plattekill Mountain
- Mohonk Preserve
- Peekamoose Blue Hole
- Hunter Mountain Resort
- Thacher State Park
- Kent Falls State Park
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Mohawk Mountain Ski Area
- Millbrook Vineyards & Winery
- Storm King Art Center
- Hudson Chatham Winery





