Vacation rentals in Monticello

4.97 out of 5 average rating, 250 reviews

Beautiful & Secluded Streamside Catskills Cabin

Private & secluded Smallwood cabin sleeps 6. Central A/C. Park & Hear the stream flowing when you pull up. Large great room with fireplace & windows overlooking backyard stream. 1 master bedroom, 1 separate guest room, 1 open sleep loft (2 twin beds) Enjoy evenings on the deck, or by the outdoor fire pit listening to the stream that leads to a small waterfall. Enjoy the swim pit right in your backyard! Outdoor Shower! Close to Bethel Woods, hiking & White Lake dining & Toronto Reservoir

Guest suite in Narrowsburg

The bathroom features a bathtub with a shower curtain, a toilet, and a vanity with a sink. A shelf is displayed beside the toilet, holding decorative items. Neutral tones are complemented by a framed floral print on the wall, enhancing the serene atmosphere.

4.96 out of 5 average rating, 204 reviews

Modern Getaway in the Catskills

Our rental unit has a private entrance with kitchen, living & dining rooms and full bath on the first floor. 1 bedroom w/ Queen bed , AC and 1/2 bath on 2nd fl. A porch w/ patio furn. a charcoal BBQ and 50 wooded acres to explore. We supply sheets, towels, kitchenware, coffeemaker and 2 flat screen satellite TVs, Internet and Wi-Fi. A great getaway for 2 adults. 20 min. to Bethel Woods 30 mins to Resorts World Casino. No smoking, pets, animals or children. All are welcome. Rainbow Friendly.

4.97 out of 5 average rating, 235 reviews

Cottage in Bethel

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

4.97 out of 5 average rating, 331 reviews

A rustic cabin is enveloped by lush greenery, showcasing ivy climbing its wooden exterior. The structure features two windows and a stone feature in the front yard, which is bordered by wild grass, enhancing the connection to the surrounding evergreen forest.

Cabin in Wurtsboro

Spring Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and gas fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

4.92 out of 5 average rating, 222 reviews

Two wooden Adirondack chairs are positioned on a dock overlooking a calm lake at sunset. A kayak with an oar rests nearby, and the water reflects vibrant hues of orange and pink, bordered by trees in the background.

Cabin in Ferndale

Charming Catskills Lakefront Home—2 hrs from NYC!

This beautiful lakefront cabin is located at the end of a peaceful road adorned with tire swings and wildflowers. It is situated in a private community on a SMALL 3 acre lake, offering the perfect setting to enjoy morning coffee on the dock, taking refreshing afternoon swims in the lake, going for evening kayaking rides, and stargazing. You can unwind in our hammock nestled amidst the ferns next to a tranquil stream. We offer 2 kayaks and 1 SUP for your enjoyment. Best of all, 2 hrs from NYC.

4.91 out of 5 average rating, 169 reviews

A wooden deck extends from the entrance, featuring two comfortable chairs positioned for outdoor relaxation. A railing surrounds the space, with greenery visible in the background, enhancing the connection to nature.

Home in Rock Hill

Beaver Lake Escape

Welcome to Beaver Lake Escape! This one bedroom, one bathroom lakeview home has all of the amenities you will need for a relaxing vacation getaway! Come experience a warm & cozy environment with full access to the community beach where you can enjoy kayaking, swimming and fishing (catch & release). You'll also find great hiking in the Spring, Summer and Fall at the Neversink Gorge Unique Area and skiing/snow boarding in the winter at Holiday Mountain! Only a 25 minute drive to Bethel Woods!

4.91 out of 5 average rating, 129 reviews

Blue House | Cedar tub•BBQ•fire pit•stargazing

Nestled in the Catskills Mountain region, between the Delaware and Hudson Rivers in the community of Monticello. Insta @bluehouseofcatskills offers a year-round retreat away from the hustle and bustle of the city. Spectacular stary nights, wildlife in the backyard, hiking trails, swimming and skiing all a short drive away. The Blue House is a wonderful getaway for all to enjoy. Modern and contemporary design the Blue House offers comfortable king and queen bedrooms and a spacious living area.

A bright living area features large windows that bring in natural light, showcasing a comfortable sectional couch and a woven chair. A dining table is positioned nearby, accompanied by a patterned rug. Wooden ceiling beams add warmth to the open space.

4.93 out of 5 average rating, 134 reviews

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.

4.99 out of 5 average rating, 186 reviews

Home in Bethel

BirchRidge A-Frame: Sauna/Firepit/Hiking/King Bed

Nestled in the Catskills Forest, less than 2 hrs from NYC you'll find Birch Ridge A-frame! This gorgeous 2 bedroom cabin is set on 6 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that create a magical stay with breathtaking views. This is the perfect place to relax, sit in the barrel sauna, hike through the private forest, roast marshmallows over the fire, and soak up the sounds of nature. A space that’s made for creating memories that will last a lifetime!

5 out of 5 average rating, 139 reviews

Bungalow in Hurleyville

Romantic Agrihood Getaway Bungalow-Fireplace/WiFi

Spend some time in a classic Catskill Bungalow! Beautifully renovated and nestled in the quiet yet all-inclusive Hamlet of Hurleyville; this clean space offers a great place to rest your head and bones. In the cooler months enjoy a beverage by the fireplace or in the warmer months have one on the porch and look out at all the green there is around. Walk to town for dinner, shopping, or a movie at the PAC (VisitHurleyville.org). Please see below for more information on our pet policy.

4.93 out of 5 average rating, 363 reviews

A spacious wooden deck is surrounded by lush green trees, providing a serene outdoor space. Modern seating options are positioned around a small dining table, with a potted plant enhancing the natural aesthetic. Large windows from the cottage offer glimpses of the inviting outdoor scenery.

Cottage in Monticello

Modern Upstate Escape with Outdoor Sauna

Newly renovated two bedroom, two bath cottage with four person barrel sauna at Swinging Bridge Reservoir, Sullivan County's largest motorboat lake. Updated amenities and mid-century and modern furniture provide a welcome respite from the city just 90 miles away. Take in the local scenery, catch a show at the Forestburgh Playhouse or stop into some of the local vineyards and restaurants. For a low key weekend, hang out by the fireplace playing some records and cooking a meal.

4.99 out of 5 average rating, 311 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Monticello vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Monticello

Superhost

A wooden deck features a pair of wrought-iron chairs and a small table, offering a serene outdoor space. Lush greenery surrounds the area, with tall trees providing shade and hills visible in the distance under a partly cloudy sky.

Home in Mountain Dale

4.77 out of 5 average rating, 91 reviews

little cozy house in the village

StarRating, 5 stars5 days ago

Great price airbnb for the exclusive space you get. Easy seamless check in/check out instructions. Features a deck & grill. Massive tv in living room with Netflix. Tons of air conditioning/fan options. Host checked in to make sure my stay was good which i appreciated

A tranquil stream flows gently over rocky beds, surrounded by lush greenery. Sunlight glimmers on the water's surface as small waterfalls cascade between stones, creating a serene atmosphere in the heart of nature.

4.95 out of 5 average rating, 77 reviews

Cozy Catskills Lake Region Cabin in Smallwood

TomasRating, 5 stars1 month ago

Absolutely loved staying in this charming cab! Nestled near stunning mountains, serene lakes, and lush green areas, the location was perfect for nature lovers. The cab itself was incredibly clean, safe, and cozy, making it a haven after a day of exploring. The hosts were super responsive and welcoming, adding to the overall great experience. Highly recommend this spot for any family looking to connect with nature in peace and tranquility. Can't wait to come back!

5 out of 5 average rating, 76 reviews

A wooden deck features two red Adirondack chairs positioned for relaxation. A grill is available for outdoor cooking, with a scenic view of the surrounding green landscape and trees in the background. Natural light enhances the inviting outdoor space.

Guesthouse in Callicoon

R52Creekside one bedroom cottage

LeslieRating, 5 stars1 week ago

Our second visit to Randy's house was absolutely fantastic! We genuinely adore his place. It's truly beautiful, serene, remarkably quiet, and spotlessly clean – we felt incredibly comfortable and settled, as if we never left home. It's the ultimate 'home away from home,' and even our mini Aussie gives it two paws up! We would enthusiastically recommend this incredible house to anyone looking for a perfect, relaxing stay.

4.97 out of 5 average rating, 30 reviews

A rustic wooden log serves as a planter, featuring a variety of vibrant herbs and plants atop a natural setting. Lush greenery surrounds the log, enhancing the serene outdoor atmosphere, while the soft sunlight filters through the trees in the background.

Tiny home in Monticello

Little red glamping cabin under the pines

HeatherRating, 5 stars8 months ago

Patti was so accommodating and very welcoming. There was firewood for us and she was incredibly communicative. Very cute little secluded spot that’s somehow also not far from some fun attractions. Thanks, Patti! Highly recommend!

5 out of 5 average rating, 34 reviews

A serene lakeside area features two wooden platforms extending over calm waters, framed by lush trees. A black wooden bench sits nearby on a stone path, surrounded by autumn foliage reflecting the warm hues of the sunset.

Cabin in Roscoe

Stunning Peaceful Lakeside Cottage

RayRating, 5 stars6 days ago

A very nice, private, place - where allows you to relax without seeing/interacting with people. Paul is also very helpful and responsive - you can get almost any help from him quickly. The cottage is great with well interior design. It has everything we need to stay in it for a week. Highly recommend to everyone who is looking for a escape from daily chores and cities. We will definitely come back and stay longer in this lovely space.

A serene waterfall cascades over dark stone ledges into a tranquil pool. Lush green trees frame the scene, their leaves reflecting sunlight filtering through the branches. The clear water glistens as it flows gently over the rocks, creating a peaceful ambiance.

4.96 out of 5 average rating, 55 reviews

Peaceful nature cabin

EdwinaRating, 5 stars8 months ago

We had the best time at Amanda s cabin in the woods. So cozy, so comfortable. It was impeccably clean. I wish I could live there. Amanda responded right away, the fact that it is pet friendly is a plus!!! I want to come back as soon as possible. If you want a little getaway, THIS is your spot. My husband, myself and our furry baby had the best cozy time ( FYI: I m all about cozy!) Thank you for everything. For those who are like me, you have found the perfect place! Enjoy 😉

Superhost

The loft space features wooden flooring and a window allowing natural light to enter. Two wall-mounted lights provide additional illumination. The space is framed by wooden railings, creating an open and airy feel in this tucked-away area.

Cottage in Bethel

4.91 out of 5 average rating, 70 reviews

Catskills Tiny Home Near Bethel Woods

MiaRating, 5 stars5 days ago

We loved our time at Jesse and Fan’s cozy tiny home! The house had everything we needed and was very comfortable. The bed was comfy and the curtains kept the room nice and dark even when the sun was rising. The yard is incredible and was teeming with small wildlife while we were there.