Family-friendly holiday rentals in Monticello

Hot Tub, Playground, 3 Acres, and Much More!

Relax with the whole family at this peaceful cottage in the trees 5 minutes from Bethel Woods - check out their upcoming events! Recently renovated cottage with hot tub, an electric fireplace, washer and dryer, dishwasher, and smart TVs. Family-friendly features include a baby gate, potty training seat, high chair, toddler-safe bunk beds, and toys Outdoor features include 2 fire pits, trampoline, jungle gym, basketball hoop, walking path, stream w/ waterfall, and 3 acres of woods to explore

Holiday-Decorated Cozy Renovated Cabin w Fireplace

Escape to The Original Bungalow, part of the @boutiquerentals_ collection—a newly renovated Scandi-chic retreat with a cozy fireplace & a fire pit in a woodland backyard. Located just 2 hours from NYC in the Catskills (one of Travel+Leisure’s 50 Best Places to Travel), Smallwood is a destination in itself: walk along the lake, waterfall or hike the forest trails. Nearby are Bethel Woods, Kartrite Waterpark, Holiday Mountain (skiing+tubing), Callicoon & Livingston Manor with dining & shopping.

Catskill mountain getaway

Fits 4 adults and 2 children.Entrance to lake 100 feet away with boat for you to use. Fish , swim , boat , picnic table , dock in middle of lake ,nearby hiking. Back patio has swing chair and picnic table , hammock for a nice quiet relaxing time .enjoy wildlife birds, deer, etc. always on standby to answer question. our local handyman is ready to address any issues you may have. Full kitchen with all your cooking needs. This is a perfect vacation spot to have fun and make beautiful memories.

Cozy Catskills Cabin

Give yourself time away from the city and closer to nature. Go for a hike, a dip in the lake, or simply relax, take your shoes off and put a good record on. Casa Smallwood got its name from the hamlet of Smallwood, a quaint community of cabins from the 30's and 40's, nestled less than 2 hours from NYC. We're only 7 minutes away from BethelWoods Arts Center, the original site of the 1969 Woodstock Festival. Come stay with us and surround yourself with beautiful trees, lakes, love and peace.

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

Modern Chalet with Hot Tub and Lake Access

Spacious home with gorgeous decks, patio areas, and hot tub, presented by StayBettr Vacation Rentals. Shared dock access is available across the street. Indoors you will discover cathedral ceilings, fireplace, and a large eat-in kitchen and living room area your group to come together. New whole house water filtration system recently installed. The entrance to the home has a ramp for accessibility, and the home has wide corridors and interior doors, so all can be included on your vacation.

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Cozy Post & Beam Barn Cabin w/Park near Bethel

1200 sq. ft Post & Beam 2 story Barn Cabin set on 18+ acres of property w/1250 ft. of rd frontage leading to this gem. Amish wood furniture and a wood burning stove. Open loft concept on 2nd floor offers 1 king bed, a trundle bed with 2 twins (sleeps 4), 1/2 bath & closet space. Downstairs offers kitchen, dining room, living room and full bath. Private park on property w/hammock, volleyball & basketball court, swing set, slide & playhouse, yard games (in house & shed) barbecue & firepit.

Canyon Edge off - grid Bungalow

The ideal perch to reflect, connect, and participate in nature's beauty. This unique structure blends pure nature with simple comfort. Sitting canyon side, you sleep beneath the canopy and wake to the mountains of the Hudson Valley. Welcome the spring buds of our forest oaks; Make summertime memories into the night by the fireside; Enjoy natures fall masterpiece of changing of the leave; Reflect on the year as the snowflakes fall Read listing fully, we’re available for any Q’s!

Private lake cabin w/hot tub, views and fruit

Catchers Pond is perched atop a hill with views overlooking a private pond featuring a swim platform, dock, Jacuzzi, outdoor shower, fire pit and a fruit orchard of peach, pear and apple. It is perfectly secluded and close to everything you might need for your stay being just 5 minutes outside Mountaindale. Its rustic, charming and wild. A great place to slow down, reconnect and watch seasons change. The cabin sits on 55 quiet acres with no other houses in sight.

Catskill Getaway Suite

Our guest suite has a private entrance adjacent to the main house with a kitchen , living room, bedroom with a full bed and full bath. Also a porch with patio furniture, a charcoal BBQ and 50 acres to explore. We supply sheets, towels, kitchenware, coffeemaker, TV, internet, Wi-Fi and AC. A great getaway for 2 adults. 20 min. from Bethel Woods for concerts, 30 min. to Resorts World Casino. All are welcome. Rainbow friendly. No smoking, children, pets or animals.