Holiday houses in Monticello

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Top-rated holiday rentals in Monticello

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A stone path leads to a tranquil outdoor area surrounded by trees, featuring several seating options including adirondack chairs. A flowing stream can be seen in the background, providing a serene backdrop to this private space.
Cabin in Bethel
4.97 out of 5 average rating, 268 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 favourite
The exterior features a charming porch with seating, surrounded by flowering plants. An American flag is displayed prominently. The building showcases a peaked roof and multiple windows, with a natural landscape of grass and trees in the background.
Guest suite in Narrowsburg
4.94 out of 5 average rating, 225 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.

Guest favourite
A hot tub is surrounded by lush greenery and illuminated by string lights, creating a serene outdoor setting. A stone path leads to the hot tub, with red chairs visible nearby, all nestled within a wooded area.
Cottage in Bethel
4.96 out of 5 average rating, 264 reviews

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

Top Guest favourite
The A-frame cabin is surrounded by trees and set on a grassy area. A fire pit with seating is situated in front, with smoke rising gently in the evening light. The cabin's large windows reveal a welcoming interior, illuminated by natural light.
Home in Bethel
5 out of 5 average rating, 214 reviews

BirchRidge A-Frame: Sauna/Firepit/King Bed/7 Acres

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 7 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that creates 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!

Guest favourite
The cabin is softly illuminated by outdoor string lights at dusk, creating a welcoming atmosphere. A stone pathway leads to a fire pit surrounded by four Adirondack chairs, while the cabin's deck features inviting seating. Lush trees provide a natural backdrop.
Cabin in Bethel
4.95 out of 5 average rating, 149 reviews

Cozy Scandi-Chic Renovated Cabin with 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.

Guest favourite
The exterior of the lake house is shown, featuring a blue facade with white trim. A small front deck with steps leads to the entrance. Lush greenery surrounds the property, providing a serene backdrop. A gravel path leads up to the house, enhancing a rural feel.
Home in Rock Hill
4.91 out of 5 average rating, 201 reviews

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!

Guest favourite
A warm living area is highlighted by a wood-burning stove at its center, surrounded by a cowhide rug. Light-colored armchairs are positioned alongside a wooden coffee table. Natural light enters through multi-pane windows, complemented by a guitar and decorative plants against the walls.
Cabin in Bethel
4.93 out of 5 average rating, 148 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.

Guest favourite
The exterior of the barn cabin features a striking stone chimney and large windows, framed by a rich red exterior and a green metal roof. The surrounding lawn is lush and well-maintained, complementing the natural setting of trees in the background.
Cabin in Bethel
4.91 out of 5 average rating, 359 reviews

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.

Guest favourite
A cozy living area is highlighted by a corner fireplace and a flat-screen television. A sectional sofa with cushions and an armchair create a comfortable seating arrangement. A decorative shelving unit displays greenery and decorative items, while warm lighting adds a welcoming touch.
Bungalow in Hurleyville
5 out of 5 average rating, 158 reviews

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.

Top Guest favourite
The living room features a spacious couch, modern lighting, and a wood-burning fireplace, with a flat-screen TV mounted above a decorative white wall. Large windows invite natural light, while sliding glass doors open to the deck. A minimalist chair adds an additional seating option.
Cottage in Monticello
4.94 out of 5 average rating, 377 reviews

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.

Guest favourite
A serene cabin is nestled among trees, overlooking a private pond. The exterior features a mix of corrugated metal and wood, blending harmoniously with the natural surroundings. A spacious outdoor area includes a fire pit and seating, offering a tranquil retreat.
Cabin in Mountain Dale
4.95 out of 5 average rating, 150 reviews

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.

Top Guest favourite
A serene view of a MidCentury bungalow, framed by lush greenery. The house, featuring large windows, is illuminated from within, reflecting a warm glow. A clear evening sky is visible, alongside the presence of the moon.
Home in Monticello
4.97 out of 5 average rating, 108 reviews

Cozy Catskills Lakeside

Serene getaway to a lakefront luxury MidCentury house 90 mins from NYC/3 hours from Philadelphia. Equipped with dock, firepit, outdoor deck and patio, guitar, instruments for family music making, games, books, and lake toys galore. 3-beds, 2-baths, fully equipped kitchen, large dining & living areas. Minutes to Callicoon, Livingston Manor, Narrowsburg, Bethel Woods, spas, Catskills Casino, Monticello Racetrack, Kartrite Waterpark, Holiday Mountain.

Popular amenities for Monticello holiday rentals

When is the best time to visit Monticello?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$249 NZD$231 NZD$281 NZD$215 NZD$217 NZD$213 NZD$283 NZD$313 NZD$356 NZD$196 NZD$176 NZD$183 NZD
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Monticello?

    Yes! Work meets play with ease at over 40 vacation rentals in Monticello featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Monticello?

    Four-legged friends are welcome in Monticello. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there Monticello vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Monticello, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly resort rentals in Monticello?

    Monticello has more than 20 family-friendly resort rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do resort rentals in Monticello have a gym?

    Absolutely! We offer over 30 resort rentals with a gym in Monticello. Enjoy a tailored experience with all the comforts you desire.

  • Do resort rentals in Monticello have wifi?

    Absolutely! We offer over 30 resort rentals with wifi in Monticello. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in resort rentals in Monticello?

    Experience the best of Monticello with our resort rentals, starting at about $21,210 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Monticello have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Monticello. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Monticello

  • Total holiday rentals

    Explore 60 holiday rentals in Monticello

  • Nightly prices starting at

    Monticello holiday rentals start at $89 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,060 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Monticello holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Monticello rentals

  • 4.8 Average rating

    Monticello stays are highly rated by guests—averaging 4.8 out of 5!

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  5. Monticello