The Nightfall Group offers an exclusive collection of luxury chalet rentals in Aspen, spanning the resort’s most coveted neighbourhoods including Aspen Mountain, the West End, Red Mountain, Starwood, and Snowmass. Working directly with homeowners, we deliver access to the finest private properties in Aspen at the best available rates.
5 bedrooms
6 bath
7 bedrooms
11 bath
17,544 sqft
Exclusive chalet inventory at the best rates The Nightfall Group works directly with Aspen homeowners to offer luxury chalet rentals across Aspen Mountain, Red Mountain, the West End, Starwood, and Snowmass at the most competitive rates available — with no hidden taxes or inflated fees that other local agencies routinely add.
24/7 local concierge team in Aspen Our concierge team is based on the ground in Aspen year-round, with onsite property managers available around the clock to handle every detail of your stay — from restaurant reservations and private chef arrangements to ski passes, heli-skiing bookings, and last-minute transfers across the resort.
Over 10 years serving A-list guests A decade of discreet, high-calibre hospitality has earned us access to Aspen’s most exclusive private chalets and mountain homes — properties that never appear on mainstream rental platforms and cannot be sourced through any other agency in the Rocky Mountains.
Priority access to restaurants, beach clubs, and nightlife in Aspen Through our long-standing local relationships, The Nightfall Group secures priority reservations at Aspen’s most sought-after restaurants, private clubs, and nightlife venues — so you arrive to confirmed tables and VIP access throughout your stay. Whether you are looking for a quiet dinner at one of Aspen’s celebrated fine dining establishments or a lively evening at the resort’s most exclusive venues, our concierge team handles every reservation in advance.
From private chefs crafting world-class culinary experiences in your chalet to personal drivers ensuring seamless transportation from Denver International Airport and Eagle County Airport, our highly trained concierge team accompanies you at every step of your Aspen stay. The Nightfall Group provides the best rates on private jet and helicopter charters into Aspen, and from securing your luxury chalet rental to recommending the finest restaurants, private clubs, and the most exclusive events and activities happening in Aspen during your visit — every detail is handled with discretion and precision.
Airport Transfers
Private Chefs
Butlers and housekeeping
Chauffeurs
Private Security
Spa And Beauty Services
Personal Training
Car Rentals
Yacht Charters
Jet Charters
Lifestyle Management
Event Management
We were two families with teenagers and it was the perfect place for our stay. The house was beautiful and comfortable - exactly like the photos. The separate bedroom/bath in the pool house worked out well for everyone to be able to spread out and have privacy.
We were looking for a house in Super Cannes during the Lions festival in Cannes, we found one which was not too high in the hills so the drive was pretty easy to the main place.
Privacy is so important to me. I was looking for a private house to rent for a week when Airbnb cancelled a reservation of mine last minute! I needed somewhere to stay for Cannes Film Festival and the The Nightfall Group found me a gorgeous mansion right away. Thank you.
Aspen Mountain / Downtown Aspen The heart of the resort, Downtown Aspen places guests steps from the Silver Queen Gondola, world-renowned restaurants, high-end boutiques, and Aspen’s most vibrant après-ski scene. Chalets and private homes in this area are among the most sought-after in the Rocky Mountains, offering the ultimate combination of ski access and village energy.
Red Mountain Aspen’s most exclusive residential address, Red Mountain sits elevated above the town with sweeping panoramic views across the Elk Mountains. The neighbourhood is home to some of the largest and most private estate properties in Aspen, favoured by guests who prioritise seclusion, space, and discretion above all else.
West End One of Aspen’s most established and charming neighbourhoods, the West End offers grand Victorian homes and luxury properties set along tree-lined streets within easy walking distance of the town centre. It is a particularly popular area for families and guests seeking a quieter residential atmosphere without sacrificing proximity to the slopes.
Starwood A gated community perched above Aspen, Starwood is one of the most private and prestigious addresses in the entire Rocky Mountain region. Properties here sit on generous plots surrounded by unspoiled wilderness, offering an unmatched level of exclusivity for guests seeking a truly secluded mountain retreat.
McLain Flats Sitting between Aspen and Snowmass, McLain Flats is home to some of the most spectacular ranch-style estate properties in the region. Wide open meadows, uninterrupted mountain views, and generous land make this neighbourhood the preferred choice for large groups, private events, and multigenerational stays.
Snowmass Village Just 12 minutes from downtown Aspen, Snowmass offers its own world-class ski area — the largest of Aspen’s four mountains — alongside a growing collection of luxury chalets and private residences. It is the ideal base for ski-focused guests who want direct slope access, a quieter village atmosphere, and exceptional value compared to central Aspen.
Peak Season: Christmas, New Year, and Presidents’ Week Aspen reaches its highest energy during Christmas week, New Year, and Presidents’ Week in February. Private chalets and luxury homes fill months in advance during these periods and the town buzzes with a festive, high-energy atmosphere. Every restaurant, private club, and après-ski venue operates at full capacity, and Aspen’s world-famous social scene is at its most vibrant. Early booking is essential — the finest luxury chalet rentals on Red Mountain and in Downtown Aspen are reserved up to a year ahead for these dates.
Mid-Season: January and Early March January and early March offer the best balance of snow conditions, availability, and value in Aspen. The resort is quieter, the slopes feel uncrowded, and the town retains its full energy without the peak-season intensity. Restaurants and private clubs remain fully open throughout, and The Nightfall Group concierge team can secure priority reservations with far greater ease during this window. This period suits families, corporate groups, and guests who prefer a more relaxed mountain experience without compromising on luxury or access.
Late Season: April April in Aspen brings longer days, warmer sunshine, and a festive end-of-season atmosphere on the mountain. The snow softens, the terraces fill, and the resort takes on a relaxed character that appeals to guests who enjoy skiing at a more leisurely pace. Many luxury chalets in Aspen offer reduced weekly rates in April, making it one of the most accessible entry points into a high-end Aspen stay. Skiing typically remains excellent through mid-April across the higher runs of Aspen Mountain and Snowmass.
Summer Season: June to September Aspen is equally spectacular in summer and increasingly popular as a year-round luxury destination. The mountains transform into world-class hiking and mountain biking terrain, the Aspen Music Festival draws international visitors, and the town’s restaurants and cultural venues operate at full swing. Luxury chalet rentals in Aspen during summer offer exceptional value compared to peak winter rates, with warm days, cool evenings, and the full Nightfall Group concierge service available throughout.
Want me to move on to getting to Aspen, the FAQ, or the meta description next?
Getting to Aspen Several convenient travel options connect Aspen with major cities across the United States and beyond. Each suits a different schedule and level of comfort. The Nightfall Group concierge team coordinates all transfers directly from your arrival point to your chalet door.
By Private Jet or Helicopter Aspen-Pitkin County Airport is one of the most popular private aviation destinations in the United States, accepting private jet and helicopter arrivals directly in the resort. The airport sits just minutes from Downtown Aspen, making it the fastest and most seamless way to arrive. The Nightfall Group coordinates all private aviation logistics, ground transfers, and onward arrangements in advance, ensuring a smooth arrival from wheels down to chalet door.
By Commercial Flight Aspen-Pitkin County Airport accepts a limited number of commercial flights from Denver, Los Angeles, and select seasonal routes. Denver International Airport is the most popular gateway for guests flying commercially, sitting approximately 4 hours by road from Aspen. Eagle County Airport in Vail, approximately 2.5 hours from Aspen, offers additional commercial connections and is a popular alternative for guests travelling from major East Coast cities.
By Road Driving to Aspen offers flexibility and some of the most spectacular mountain scenery in North America. The resort is accessible from Denver via Interstate 70 and Highway 82 through Glenwood Canyon — a dramatic and iconic approach through the Rocky Mountains. The drive takes approximately 4 hours in clear conditions. Winter driving conditions require appropriate tyres and preparation, and The Nightfall Group can arrange fully managed chauffeur transfers from Denver or Eagle County for guests who prefer a stress-free road journey.
By Train and Bus Amtrak’s California Zephyr connects Chicago and San Francisco with Glenwood Springs, approximately 45 minutes from Aspen by road. RFTA’s Roaring Fork Transportation Authority bus service runs regularly between Glenwood Springs, Basalt, and Aspen, offering an affordable and scenic connection for guests travelling without a car. The Nightfall Group can arrange onward transfers from Glenwood Springs directly to your chalet in Aspen.
Booking a luxury chalet rental in Aspen with The Nightfall Group is straightforward and fully guided. Browse our curated collection of Aspen properties, fill out the reservation form with your dates, group size, and preferences, and a chalet specialist will contact you promptly to confirm availability. The Nightfall Group concierge team then handles all pre-arrival arrangements so everything is in place before you arrive in Aspen.
The Nightfall Group is one of the most experienced luxury chalet and private home rental agencies operating in Aspen. With over 10 years of experience serving A-list guests across the world’s most exclusive mountain destinations, our team maintains direct relationships with Aspen homeowners and a portfolio that includes off-market properties unavailable through any other agency.
For peak periods — Christmas, New Year, and Presidents’ Week in February — book 6 to 12 months in advance. The finest luxury chalet rentals on Red Mountain and in Downtown Aspen fill the previous spring. Outside peak periods, 2 to 3 months is generally sufficient. Contacting The Nightfall Group early always opens access to off-market inventory that other Aspen agencies cannot offer.
Luxury chalet rentals in Aspen vary widely depending on the property, neighbourhood, and time of year. Red Mountain and Starwood estate properties command the highest rates during peak weeks, while Snowmass and McLain Flats offer exceptional value at a more accessible price point. The Nightfall Group provides a full and transparent cost breakdown before you confirm your booking, with no hidden fees or inflated charges added on top.
The total cost of a luxury chalet rental in Aspen includes the base nightly rate, applicable local taxes, and any additional charges for services such as private chefs, event hosting, pets, or early check-in and late check-out. The Nightfall Group provides a complete and transparent breakdown upfront, making us one of the most straightforward luxury rental agencies operating in Aspen.
Most luxury chalet rentals in Aspen require a minimum stay of 7 nights, with many properties operating on a Saturday to Saturday schedule during peak season. Shorter stays may be available during mid-season and summer depending on the property. The Nightfall Group advises on minimum stay requirements for each Aspen chalet during your initial consultation.
Most luxury chalet rentals in Aspen include daily housekeeping as standard. Many properties in The Nightfall Group’s Aspen collection come with full-time staff including private chefs, butlers, housekeepers, and personal drivers. The concierge team coordinates all staffing in advance so guests arrive to a fully prepared property with every detail already in place.
The best area in Aspen for a luxury chalet rental depends entirely on your priorities. Red Mountain and Starwood suit guests seeking maximum privacy, seclusion, and estate-scale properties. Downtown Aspen and the West End are ideal for guests who want restaurants, boutiques, and the gondola within walking distance. McLain Flats suits large groups and private events. Snowmass is the best choice for ski-focused guests wanting direct slope access at a quieter pace. The Nightfall Group advises on the right neighbourhood for every group during the initial consultation.
Several properties in The Nightfall Group’s Aspen collection offer ski-in ski-out access or sit within a short distance of the nearest lift. Snowmass in particular offers excellent ski-in ski-out inventory across a range of property sizes. Guests should specify ski-in ski-out as a priority when making an enquiry so the team can match the right Aspen property to your needs.
Yes. Many properties in The Nightfall Group’s Aspen collection work exceptionally well for families, featuring large living areas, multiple en-suite bedrooms, and private outdoor spaces suited to all ages. The concierge team can arrange ski school enrolment, childcare, children’s activity planning, and pre-arrival grocery provisioning for families travelling to Aspen with young children.
Yes. Several properties in The Nightfall Group’s Aspen collection are ideally suited to private events, corporate retreats, and exclusive gatherings. Large estate chalets on Red Mountain, Starwood, and McLain Flats provide exceptional settings for group events with full staff, private catering, and dedicated entertainment arrangements. All event plans should be declared at the time of booking and the concierge team manages all logistics from arrival to departure.
Yes. Aspen is a thriving year-round destination and one of the most popular summer luxury travel destinations in North America. The mountains open for world-class hiking and mountain biking, the Aspen Music Festival draws international visitors, and the town’s restaurants and cultural venues operate throughout the warmer months. Luxury chalet rentals in Aspen during summer offer exceptional value compared to peak winter rates, with the full Nightfall Group concierge service available throughout your stay.
Aspen stands apart from European ski resorts through its combination of Rocky Mountain terrain, a vibrant cultural scene, and a town that functions as a world-class destination in its own right year-round. Compared to Courchevel or Megève, Aspen offers a distinctly American luxury experience — larger properties, wider open spaces, and a social scene that blends skiing with art, music, and fine dining at the highest level. The Nightfall Group operates across both Aspen and the French Alps, and can advise which destination best suits your group.
Yes. The Nightfall Group arranges private chefs for luxury chalet rentals across Aspen as part of its full concierge service. Chefs are briefed in advance on dietary requirements, preferences, and any special occasions during the stay. From casual family dinners to formal multi-course tasting menus, the culinary experience is tailored entirely around the guest and can be arranged for the full duration of the stay or for specific evenings.
Yes. The Nightfall Group coordinates private jet arrivals into Aspen-Pitkin County Airport and helicopter transfers from Denver and other major hubs. The concierge team manages all aviation logistics, ground transfers, and onward arrangements, ensuring a seamless journey from departure to chalet door. Private aviation into Aspen is one of the most popular arrival options among our guests and the team has extensive experience coordinating these arrangements.
The Nightfall Group provides a 24/7 on-the-ground concierge service for all luxury chalet rentals in Aspen. The team handles restaurant reservations, private club access, last-minute transfers, ski pass arrangements, and any in-resort logistics at any hour. Every guest works with a single dedicated point of contact available from pre-arrival planning through to final departure from Aspen.
The Nightfall Group is available around the clock via multiple channels. Reach the team by WhatsApp at +1 (310) 666-7012, by email at support@nightfallgroup.com, or by phone at +1 (310) 666-7012. The concierge team responds promptly and can confirm availability, begin the booking process, and answer any questions about luxury chalet rentals in Aspen immediately.
1
Need Help? Chat with us
