Vacation rentals in Monticello

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Top-rated vacation rentals in Monticello

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Guest favorite
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, 270 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

Guest favorite
Cabin in Bethel
4.94 out of 5 average rating, 159 reviews

Fireplace—Renovated—Near Skiing & Tubing—Chic+Cozy

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

Guest favorite
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
4.99 out of 5 average rating, 232 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 favorite
A rustic cabin is positioned among lush trees, featuring a cozy front porch with wooden steps. The exterior showcases natural tones, complemented by decorative wildlife silhouettes. An expansive grassy area surrounds the cabin, inviting outdoor activities.
Cabin in Ferndale
4.88 out of 5 average rating, 292 reviews

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.

Guest favorite
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, 152 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 favorite
The exterior of the bungalow is showcased, set against a backdrop of trees and a partly cloudy sky. A spacious deck is equipped with chairs, while a fire pit is surrounded by outdoor seating. A stack of firewood is neatly arranged nearby.
Cottage in Ferndale
4.94 out of 5 average rating, 126 reviews

Barton bungalow cozy relaxation on 7private acres

Stay at the Barton Bungalow! This cozy, beautifully renovated bungalow sits on 7 private acres. It has a rustic feel with all the modern amenities. We have high speed WiFi so you can work from home. Enjoy some R&R in the hammock, relax by the fire pit or bbq . We are 2 miles from Walnut Mountain Park and less than 10 miles away from Bethel Woods. Try your luck at Resorts World Catskills or go for a splash at Kartrite indoor water park. The trendy Livingston Manor is less than 20 minutes away

Guest favorite
Cabin in Bethel
4.91 out of 5 average rating, 364 reviews

Cozy Barn Cabin near Ski Mountain & Bethel Woods

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.

Top guest favorite
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, 385 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.

Top guest favorite
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, 160 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.

Guest favorite
Cottage in Bethel
4.91 out of 5 average rating, 153 reviews

Lovely Cottage w/ Jacuzzi+Woodstove!

Nestled in the hamlet of Smallwood, only 2 hours from NYC, this newly renovated cottage is the perfect getaway from the city and an oasis surrounded by nature. This cottage is perfectly located for access to surrounding lakes and seasonal beaches, hiking trails as well as exploring and discovering the lovely Catskills region. The cottage features a wood stove, spacious deck, a fire pit as well as an all-season jacuzzi to enjoy day or night.

Guest favorite
A modern house with a large glass wall is nestled among tall trees beside a serene waterway. A spacious deck extends from the home, offering a view of the surroundings. The landscape features a gently sloping yard leading to the water's edge.
Home in Monticello
4.97 out of 5 average rating, 155 reviews

Secluded lakefront home With an EV charger

Welcome to your oasis on the Swiniging Bridge Reservoir! Only 90 minutes from NYC, but a world away. A complete glass wall facing the water allows guests to take in the views and sounds of a babbling brook that feeds into a motorboat lake. This brand new house sleeps 6 adults (or 4 adults and 3 children) and features a full kitchen, free WiFi, bedding, linens, and toiletries. A canoe and paddleboat are also available for your use!

Top guest favorite
A charming cabin exterior features a bright red façade surrounded by lush greenery. A welcoming front porch with two wooden chairs overlooks the landscaped yard, while a stone pathway leads to the entrance. Large windows allow natural light into the space.
Cabin in Woodridge
5 out of 5 average rating, 118 reviews

Escape to a 3-Bedroom Cabin in Lower Catskills

Welcome to the Bear Lodge! Located in the Lower Catskills, the cabin is a short 90 minutes from NYC, and is centrally located to all kinds of outdoor activities. There are easy walking trails through the woods within walking distance, as well as Rails-to-Trails paths, the Neversink River, and dozens of lakes nearby

Popular amenities for Monticello vacation rentals

When is the best time to visit Monticello?

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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 house rentals in Monticello?

    Experience the best of Monticello with our house rentals, starting at about $120 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 vacation rentals in Monticello

  • Total vacation rentals

    Explore 60 vacation rentals in Monticello

  • Nightly prices starting at

    Monticello vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 1,100 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Monticello vacation rentals include wi-fi access

  • Popular amenities for guests

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

  • 4.7 Average rating

    Monticello stays receive an average rating of 4.7 out of 5 from guests

  1. Airbnb
  2. United States
  3. New York
  4. Sullivan County
  5. Monticello