Monticello holiday rentals

We found 1,036 holiday rentals — enter your dates for availability
Discover a selection of 27 homes, 10 cabins and other holiday rentals in Monticello that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, which might include a fireplace and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Monticello

Showing deals for:25 Dec - 1 Jan

Exterior side photo with extra large patio that includes large outdoor table and seats and barbecues
Dining and front TV room with beautiful outdoor view of the mountains
Interior
Living or TV area at front entrance of cabin
Exceptional
(9 reviews)

The Luxury Cabin at Deep Hollow

Narrowsburg

16% off
AU$10,117
for 7 nights, 1 cabin
AU$1,445 per night
includes taxes & fees
The Luxury Cabin at Deep Hollow
Exterior
Property grounds
Sun-room with french doors
View from rear of house, standing at sin-room entryway.
Exceptional
(39 reviews)

Waterfront property, perfect winter getaway, directly on the Willowemoc!

Livingston Manor

11% off
AU$2,311
for 7 nights, 1 cabin
AU$330 per night
includes taxes & fees
Waterfront property, perfect winter getaway, directly on the Willowemoc!
Dining
Dining
Room
Interior
Exceptional
(5 reviews)

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Forestburgh

16% off
AU$6,592
for 7 nights, 1 chalet
AU$942 per night
includes taxes & fees
Serenity at Lake Joseph | Lakefront•Hot Tub•Ski
The fields
The house
the house
Second floor Hallway
Exceptional
(89 reviews)

The Stone Wall Property on 25 acres with private lake

Hurleyville

8% off
AU$3,539
for 7 nights, 1 cottage
AU$506 per night
includes taxes & fees
The Stone Wall Property on 25 acres with private lake
Exterior
Terrace/patio
Private kitchen
Interior
Exceptional
(27 reviews)

Private log cabin nestled at the base of a secluded wooded area

Yulan

8% off
AU$7,223
for 7 nights, 1 home
AU$1,032 per night
includes taxes & fees
Private log cabin nestled at the base of a secluded wooded area
Living area
Interior
Indoor spa tub
Pool
Exceptional
(43 reviews)

Hemlock Estate: Indoor Hot Tub, Pool, Game Room; Spacious, Ski & More!

Monticello

8% off
AU$8,881
for 7 nights, 1 villa
AU$1,269 per night
includes taxes & fees
Hemlock Estate: Indoor Hot Tub, Pool, Game Room; Spacious, Ski & More!
Redesigned safe and well lit staircase and path.
The view as you enter the front door.
Enjoy the peaceful setting and the ever changing lake views.
Peaceful & Quiet Winter Retreat. Enjoy a warm fire and view the iced over lake.
Exceptional
(207 reviews)

Relaxing Lakefront, Very Clean. Great for Families.

Bethel

9% off
AU$4,148
for 7 nights, 1 home
AU$593 per night
includes taxes & fees
Relaxing Lakefront, Very Clean. Great for Families.
Living area
Living area
Property grounds
Living area
Exceptional
(48 reviews)

Wood Cabin in Catskill NYS

Woodbourne

12% off
AU$9,523
for 7 nights, 1 cabin
AU$1,360 per night
includes taxes & fees
Wood Cabin in Catskill NYS
Private kitchen
Living area
Room
Interior
Exceptional
(7 reviews)

lake/fireplace

Greeley

9% off
AU$51,061
for 7 nights, 1 home
AU$7,294 per night
includes taxes & fees
lake/fireplace
Property grounds
Private kitchen
Living area
Interior
Exceptional
(5 reviews)

Charming 2-bedroom Country Cottage with Hot Tub

Obernburg

12% off
AU$5,481
for 7 nights, 1 cottage
AU$783 per night
includes taxes & fees
Charming 2-bedroom Country Cottage with Hot Tub
Pool
Exterior
Living area
Interior
Exceptional
(8 reviews)

Luxe, Secluded Catskill Lodge Heated Pool, Hot Tub

Ellenville

8% off
AU$14,670
for 7 nights, 1 home
AU$2,096 per night
includes taxes & fees
Luxe, Secluded Catskill Lodge Heated Pool, Hot Tub
Private Lake Area
House with Screen Room
Interior
Living area
Exceptional
(31 reviews)

Beautiful Chalet with Private Lake Spot Near Popular Resorts - Wurtsboro NY!

Wurtsboro

8% off
AU$2,693
for 7 nights, 1 chalet
AU$385 per night
includes taxes & fees
Beautiful Chalet with Private Lake Spot Near Popular Resorts - Wurtsboro NY!
Interior
Outdoor dining
Exterior
Living area
Exceptional
(9 reviews)

Immerse in your private woods in our modern cabin

Livingston Manor

11% off
AU$3,990
for 7 nights, 1 cabin
AU$570 per night
includes taxes & fees
Immerse in your private woods in our modern cabin
Heated pool open from Memorial Day Weekend thru the end of September
Hot tub on the deck and open year round
Kitchen
Family room with wood stove
Excellent
(13 reviews)

Casa Nera | Heated Pool • Hot Tub • Ski

Swan Lake

16% off
AU$6,592
for 7 nights, 1 home
AU$942 per night
includes taxes & fees
Casa Nera | Heated Pool • Hot Tub • Ski
Private kitchen
Pool
Dining
Exterior
Exceptional
(88 reviews)

Private Hilltop Getaway with Hot Tub & Saltwater Heated Pool

Damascus

8% off
AU$7,169
for 7 nights, 1 home
AU$1,024 per night
includes taxes & fees
Private Hilltop Getaway with Hot Tub & Saltwater Heated Pool
Living area
Terrace/patio
Large window in loft for evening star gazing or morning views into the pasture.
Interior
Exceptional
(6 reviews)

Milk House @ Indigo Bunting Farm

Callicoon Center

8% off
AU$4,277
for 7 nights, 1 cottage
AU$611 per night
includes taxes & fees
Milk House @ Indigo Bunting Farm
Property grounds
Private kitchen
Exterior
Private kitchen
Very good
(28 reviews)

Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

Monticello

8% off
AU$12,039
for 7 nights, 1 home
AU$1,720 per night
includes taxes & fees
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski
Interior
Dining
Living area
2 Twin Beds
Exceptional
(6 reviews)

Cozy Catskills Farmhouse in Barryville near the Delaware River

Barryville

7% off
AU$2,934
for 7 nights, 1 home
AU$419 per night
includes taxes & fees
Cozy Catskills Farmhouse in Barryville near the Delaware River
Dining
Outdoor dining
Firewood for the fire pit.
Interior
Exceptional
(36 reviews)

Lakefront family friendly peaceful Catskills retreat!

Wurtsboro

8% off
AU$4,896
for 7 nights, 1 home
AU$699 per night
includes taxes & fees
Lakefront family friendly peaceful Catskills retreat!
Outdoor fire pit with comfy chairs
Dining table with 8 chairs
Kitchen island
Room
Exceptional
(13 reviews)

Private vollyball court: 5-Acre Haven with AC close to Bethel Woods.

Narrowsburg

12% off
AU$5,083
for 7 nights, 1 home
AU$726 per night
includes taxes & fees
Private vollyball court: 5-Acre Haven with AC close to Bethel Woods.
Interior
Dining
Living area
Outdoor dining
Exceptional
(7 reviews)

Dancing Doe Estate with Wood Stove, Hot Tub & Firepit

Jeffersonville

12% off
AU$5,583
for 7 nights, 1 home
AU$798 per night
includes taxes & fees
Dancing Doe Estate with Wood Stove, Hot Tub & Firepit
Private kitchen
Exterior
Spacious dining for 6-8 with optional leaf and extra chairs
Property grounds
Exceptional
(11 reviews)

Private 5-Acre Farmhouse Retreat - Bethel Woods 25 mins - Sleeps 8

Livingston Manor

8% off
AU$5,070
for 7 nights, 1 home
AU$724 per night
includes taxes & fees
Private 5-Acre Farmhouse Retreat - Bethel Woods 25 mins - Sleeps 8
Newly renovated living room with a massive pit couch
Lake front slate patio with fire pit.
Marina
Exterior
Exceptional
(18 reviews)

Enjoy the Magic of the Catskills in your Private Lakefront Home

White Lake

8% off
AU$5,759
for 7 nights, 1 home
AU$823 per night
includes taxes & fees
Enjoy the Magic of the Catskills in your Private Lakefront Home
Room
Exterior
Living area
Outdoor dining
Exceptional
(11 reviews)

Cozy 1-bedroom cabin in amazing Milford with WiFi, AC next to stream.

Milford

8% off
AU$2,221
for 7 nights, 1 cabin
AU$317 per night
includes taxes & fees
Cozy 1-bedroom cabin in amazing Milford with WiFi, AC next to stream.

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The lush setting of Monticello is ready to explore

Come and experience Monticello and its entertainment, churches and architecture. This city's forests, theatres and hiking draw many visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Monticello

Do you want to find attractions to visit during your stay? Venture out of your cosy holiday rental and check out everything that makes Monticello a fun place to get away to. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Monticello Motor Club (2.4 mi / 3.8 km)
  • Concord Monster Golf Course (2.4 mi / 3.8 km)
  • Tarry Brae Golf Course (5.7 mi / 9.2 km)
  • Sullivan County Golf and Country Club (10.7 mi / 17.2 km)
  • Ski Big Bear at Masthope Mountain (19.3 mi / 31 km)
  • Brimstone Hill Winery (19.5 mi / 31.4 km)

Exploring the natural features in Monticello

Whether you're looking for adventure or just want to spend some time taking in the scenery, Monticello is a great place to get out in nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Sackett Lake (3.3 mi / 5.4 km)
  • Lake Louise Marie (6.2 mi / 10 km)
  • Neversink River (8.2 mi / 13.2 km)
  • Lake Superior State Park (9.9 mi / 15.9 km)
  • Woodstock Monument (10.4 mi / 16.8 km)
  • Mohican Lake (11.2 mi / 18 km)

How to get to and around Monticello

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 33 mi (53.1 km) from the city centre.

Frequently asked questions

What is the best area to stay in Monticello when booking a holiday rental?
When considering a holiday rental in Monticello, New York, the area surrounding the town centre is an excellent choice. This vibrant neighbourhood boasts a variety of properties that cater to different tastes and budgets, making it an appealing option for visitors.Staying near the town centre puts you in close proximity to several top attractions. One standout is the Bethel Woods Centre for the Arts, which is not only a premier venue for concerts and performances but also features a museum dedicated to the 1969 Woodstock Festival. Additionally, the nearby Monticello Casino and Raceway offers a lively option for those looking to try their luck or enjoy a night out.The neighbourhood itself offers a charming mix of local shops and eateries, providing a taste of the area's culture and community.*You must be at least 18 years old to participate in gambling activities in the United Kingdom. Please gamble responsibly. If you feel that gambling is affecting your life, seek help from organisations such as BeGambleAware at www.begambleaware.org or call their helpline at 0808 8020 133.
Where are the best areas for renting a beach house in Monticello?
For renting a beach house in Monticello, consider looking in the nearby areas around the beautiful lakes, particularly the ones associated with the Catskills region. The area surrounding White Lake is popular for holiday rentals, offering properties that often feature spacious decks, waterfront access, and amenities such as BBQ grills and outdoor dining areas, great for enjoying the serene lake views.Additionally, the vicinity of Lake Superior and the town of Bethel provides further options, with some rentals boasting private docks and access to water activities like kayaking and fishing. Many of these properties are equipped with modern kitchens, allowing for convenient self-catering, and some even include amenities like fire pits for evening gatherings under the stars.The region itself is known for its natural beauty, with opportunities for hiking and exploring the lush surroundings. Monticello is also close to various attractions, including the Bethel Woods Centre for the Arts, which adds cultural interest for visitors.
Where are the best Monticello ski resort rentals?
For the best ski resort rentals near Monticello, New York, travellers should consider the nearby area of White Lake, which offers convenient access to the slopes of the Holiday Mountain Ski & Fun Park. This region features a variety of rental options, ranging from cozy cabins to spacious lodges, ideal for families and groups. Many properties come equipped with essential amenities such as full kitchens, comfortable living areas, and outdoor spaces, superb for enjoying a hot drink after a day on the slopes.In addition to White Lake, the nearby town of Bethel provides additional rental opportunities. Here, visitors can find charming chalets and modern homes, often featuring amenities like fireplaces, game rooms, and even hot tubs, enhancing the après-ski experience. The Bethel area is also known for its vibrant cultural scene, with proximity to the Bethel Woods Centre for the Arts, making it a great spot for those looking to combine outdoor activities with entertainment.For those interested in exploring the outdoors beyond skiing, the Catskill Mountains are not far and offer numerous hiking trails and scenic vistas. Rentals in the surrounding areas often provide a rustic charm, with easy access to both nature and local dining options.
What is the most popular type of holiday rental accomodation in Monticello?
In Monticello, holiday houses are the most popular type of holiday rental, with around 60 available throughout the area. These properties often come with spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many holiday houses also feature outdoor spaces, such as decks or gardens, for relaxing after a day of exploring the nearby attractions. Additionally, there are about 27 cabins and several chalets and villas, which provide a unique, rustic charm and are superb for those looking to immerse themselves in nature.
Are there any family house rentals in Monticello?
In Monticello, New York, there are numerous family-friendly house rentals available, with around 28 options to choose from. This charming town is surrounded by the scenic beauty of the Catskills, making it an excellent base for families looking to explore the outdoors. Many of these homes come equipped with spacious living areas, fully stocked kitchens for preparing family meals, and outdoor spaces where children can play and enjoy the fresh air.Visitors will appreciate the proximity to various attractions, such as the nearby Bethel Woods Centre for the Arts and the stunning lakes and hiking trails in the region. Moreover, amenities like Wi-Fi and air conditioning are typically included, ensuring a comfortable stay for all.
Can I rent a holiday home with a pool or hot tub in Monticello?
In Monticello, New York, there are several holiday homes available for rent that feature pools and hot tubs. This area is known for its beautiful natural surroundings and is a great destination for those looking to relax and enjoy outdoor activities. Many of the properties come with amenities such as private pools, hot tubs, and spacious outdoor areas, great for unwinding after a day of exploring. Additionally, fully equipped kitchens are common, allowing guests to prepare their own meals comfortably. Monticello's proximity to attractions like the Catskill Mountains and local lakes enhances the appeal, providing ample opportunities for hiking, fishing, and enjoying nature.
Are there pet-friendly house rentals in Monticello?
In Monticello, there are numerous pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come with amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, making them comfortable for families or groups.The area offers a blend of natural beauty and recreational activities, with nearby attractions including the scenic Catskill Mountains, which provide ample opportunities for hiking and exploring nature with pets. Additionally, the nearby Monticello Casino and Raceway adds an element of entertainment for visitors.*You must be at least 18 years old to participate in gambling activities in the United Kingdom. Please gamble responsibly. If you feel that gambling is affecting your life, seek help from organisations such as BeGambleAware at www.begambleaware.org or call their helpline at 0808 8020 133.
Are there any remote work holiday rentals in Monticello?
In Monticello, New York, there are numerous holiday rentals suitable for remote work, with around 87 options available. Many of these properties are equipped with reliable Wi-Fi, ensuring that you can stay connected while enjoying your stay. Expect to find amenities such as dedicated workspaces, comfortable seating areas, and fully equipped kitchens, allowing for a productive and pleasant working environment.The region is known for its picturesque landscapes, making it a lovely backdrop for your work-from-home experience. You can find properties ranging from cosy cabins to spacious homes, often featuring outdoor spaces where you can relax during breaks. Monticello's proximity to local amenities, including shops and restaurants, adds convenience for those balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Monticello?
In Monticello, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoying the natural surroundings. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, rentals often come with coffee and tea makers for a warm beverage at any time, and some properties are pet-friendly, suiting travellers who wish to bring their furry companions along.
What are the top attractions in Monticello?
In Monticello, visitors can explore a range of attractions that showcase the area's natural beauty and local culture. The Monticello Casino and Raceway offers entertainment and gaming options, making it a popular spot for those looking to enjoy a night out. Nature enthusiasts can visit the nearby Bethel Woods Centre for the Arts, which not only provides concert venues but also features beautiful grounds that are great for outdoor activities and events.For outdoor adventures, the surrounding Catskill Mountains offer numerous hiking trails and scenic views, making it an excellent destination for those who appreciate nature. Additionally, the nearby Sullivan County Museum provides insights into the region's history and culture, showcasing local art and artifacts.Families can enjoy the attractions at the nearby Holiday Mountain Ski and Fun Park, which offers a variety of recreational activities throughout the year, including skiing in the winter and water slides in the summer.*You must be at least 18 years old to participate in gambling activities in the United Kingdom. Please gamble responsibly. If you feel that gambling is affecting your life, seek help from organisations such as BeGambleAware at www.begambleaware.org or call their helpline at 0808 8020 133.
Are all fees included in the Monticello holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Monticello holiday homes with parking?
Stayz offers a wide selection of holiday homes in Monticello with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Monticello holiday homes?
You can find great discounts on holiday homes in Monticello on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Monticello holiday home booking on Stayz?
To find Monticello holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Monticello?
A long-stay holiday home in Monticello is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Monticello holiday home?
Book your Monticello holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Monticello?
Prices for holiday homes in Monticello vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Monticello to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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