Chestnut Lodging

Rent a vacation rental home at Chestnut Mountain Resort, Illinois, United States. Located near the historic town of Galena, high above the Mississippi River it has become a premier Midwest ski destination with its nineteen trails that span 220 rolling acres with a total vertical drop of 475 feet. Book your vacation rentals directly from owners of chalet rentals, cabins, homes, and condo accommodations at Chestnut Mountain Resort, IL, USA.

Only in the Midwest will you find such an unexpected diamond in the rough high above the Mississippi, tucked nicely in the hills near Galena. Midwesterners love their elbow room and Chestnut Mountain is no exception. Thanks to two quads, four triple chair lifts, and three surface lifts, lines are virtually non-existent.

When darkness falls, great skiing and awesome views continue outside. But that's also just about the time things get exciting inside. Chestnut Mountain has 100 slopeside rooms in close proximity to an indoor pool, sauna and jacuzzi. The Sunset Grille restaurant serves up fine dining favorites and festive nightlife gets a leg up thanks to the frequent live music, an electronic game room and the Three Gables Lounge. Galena, eight miles away, also has great dining and entertainment options.

During summertime there is no shortage of activities for the young or young at heart. Ride the Alpine Slide or cruise the river on a Mississippi Explorer Cruise. Bike or hike trails showcasing the area's unique geologic beauty. Or test your short game on our 18-hole mini golf course. Whatever it is you want to do on a mountain, chances are you can do it here. Chestnut Mountain has all the amenities you've come to expect in a resort destination, yet its midwestern roots and small town charm always keeps folks coming back for more.

Chestnut Mountain is a perfect vacation spot with lodging such as condo rentals, chalet rentals and private vacation home rentals. If you own a vacation rental or a chalet rental there is no upfront cost when you list your vacation rental accommodations (condos, chalets, homes) with Owner Direct Vacation Rentals.

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10 Vacation Rentals

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  • Linea Furnished Jr. One Bedroom

    Linea Furnished Jr. One

    Chicago: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 5
    • #238275
    $126 to $216 USD/night Credit Card Paypal Pet Friendly
    Modern. Clean. All-Inclusive. Enjoy stunning city views from this cement loft style apartment just steps from the Chicago Riverwalk and Randolph Theater District. This Jr. One Bedroom apartment is centrally located in Downtown Chicago, giving you the luxury of premiere shopping, dining, and big city attractions at your doorstep. This apartment includes a bedroom area with King Bed and living room with modern amenities. It features exposed concrete ceilings, matte grey and white cabinetry, stainless steel appliances, dark wood-grained flooring, sound-engineered glass, a queen pull-out sofa and a washer/dryer in the apartment. Relax after work with the endless resort-style amenities in the building, including a fitness center, indoor/outdoor pool with retractable walls, 24-hour door staff, skyline sundeck, dog spa + dog walk, media room and billiards room. Please note that amenities will be available to you in a nearby building until September 2017, as this building is brand new. Arrive with just your suitcase and we handle everything else for you. Your automated monthly payment includes all furnishings, linens, kitchen and household items, high speed wireless Internet, unlimited calling nationwide, all utilities, cable TV with flat screen TV/s, access to all amenities, 24-hour maintenance and 24-hour customer service. We offer month to month contracts with a 31 night minimum and a 14 day notice to vacate. Parking and maid service are available, and apartment prices depend on your dates of stay. Book today to start your Chicago experience!
  • Linea Furnished Studio

    Linea Furnished Studio

    Chicago: Apartment
    • 1 BA
    • Sleeps 3
    • #238274
    $115 to $205 USD/night Credit Card Paypal
    Modern. Clean. All-Inclusive. Enjoy stunning city views from this cement loft style apartment just steps from the Chicago Riverwalk and Randolph Theater District. This Studio apartment is centrally located in Downtown Chicago, giving you the luxury of premiere shopping, dining, and big city attractions at your doorstep. This apartment includes a bedroom area with King Bed and living room area. It features exposed concrete ceilings, matte grey and white cabinetry, stainless steel appliances, dark wood-grained flooring, sound-engineered glass, and a washer/dryer in the apartment. Relax after work with the endless resort-style amenities in the building, including a fitness center, indoor/outdoor pool with retractable walls, 24-hour door staff, skyline sundeck, dog spa + dog walk, media room and billiards room. Please note that amenities will be available to you in a nearby building until September 2017, as this building is brand new. Arrive with just your suitcase and we handle everything else for you. Your automated monthly payment includes all furnishings, linens, kitchen and household items, high speed wireless Internet, unlimited calling nationwide, all utilities, cable TV with flat screen TV/s, access to all amenities, 24-hour maintenance and 24-hour customer service. We offer month to month contracts with a 31 night minimum and a 14 day notice to vacate. Parking and maid service are available, and apartment prices depend on your dates of stay. Book today to start your Chicago experience!
  • Modern Greek Town one Bedroom Furnished Rental

    Modern Greek Town one

    Chicago: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 5
    • #238206
    $109 to $143 USD/night Credit Card Pet Friendly
    Modern. Clean. All-Inclusive. Enjoy stunning east city views from this luxury apartment, walk to work and enjoy hundreds of restaurants in the evening. This luxurious apartment includes a full bedroom with king bed, living room with queen pull-out sofa, achef-inspired kitchen with white quartz countertops, two-tone cabinetry with soft-close drawers and doors, white glass mosaic tile backsplash, stainless steel appliances, gas stoves, custom wide-plank flooring, walk-in closet, in-unit washer and dryer and controlled heating/air. This 24-hour doorman building features an expansive 24,000 square foot outdoor sundeck including an outdoor pool and hot tub, lounge seating, fire pit, private kitchen, yoga studio and grills. Inside you will find a fitness center with towel service, business center, billiards room with TV, party room, complimentary coffee bar, on-site micro market, private dog run and grooming station and a bike room. Arrive with just your suitcase and we handle everything else for you. Your automated monthly payment includes all furnishings, linens, kitchen and household items, high speed wireless Internet, unlimited calling nationwide, all utilities, cable TV with flat screen TV/s, access to all amenities, 24-hour maintenance and 24-hour customer service. We offer month to month contracts with a 31 night minimum and a 14 day notice to vacate. Parking and maid service are available, and apartment prices depend on your dates of stay. Book today to start your Chicago experience!
  • All-Inclusive Luxury Studio in Greek Town

    All-Inclusive Luxury

    Chicago: Apartment
    • 1 BA
    • Sleeps 3
    • #234228
    $148 to $170 USD/night Credit Card Paypal Pet Friendly
    This stunning location with unobstructed city views is walking distance to the loop (business district), theater, west loop (Randolph St. Restaurant row), public transportation and recreation. Our apartments are fully furnished to the smallest detail, so you only need your suitcase. If there is something that would make your stay more comfortable, just ask. We pride ourselves on delivering top customer satisfaction, each and every time. Guests will have access to the entire apartment. Your apartment will include custom wide plank flooring, stainless steel appliances, elegant white quartz countertops in the kitchen and bath, modern fixtures, oversized walk-in closets and full size washer and dryer. We will also provide you with all kitchenware, linens, television, wifi, telephone, heating/cooling, electricity and everything else you need to be comfortable. The building amenities include an expansive fitness center and outdoor yoga studio, 24,000 SF outdoor sundeck with fire pits and grills, heated outdoor pool and hot tub, game room with billiards and 60” TV, party room with chef’s kitchen, technology lounge with complimentary coffee, 24/7 market with food and beverage options, bike storage and more. We professionally clean each property before your arrival, including every kitchen item and every linen in the property to ensure your complete satisfaction. We deliver 24-hour maintenance service to ensure your apartment stays in top condition for your entire stay.
  • All-Inclusive River North Luxu Jr. One Bedroom

    All-Inclusive River North

    Chicago: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 5
    • #234226
    $126 to $216 USD/night Credit Card Paypal Pet Friendly
    This River North location is surrounded by award winning restaurants and nightlife. Walk to the loop (business district), theater, magnificent mile, public transportation and river walk. The apartment is 961 SF and finished with granite countertops, stainless steel appliances, hardwood floors and modern furniture. The building includes resort level amenities such as a pool with private cabanas, fitness center and business center. Our apartments are fully furnished to the smallest detail, so you only need your suitcase. If there is something that would make your stay more comfortable, just ask. We pride ourselves on delivering top customer satisfaction, each and every time. Your apartment will include wood flooring, stainless steel appliances, elegant granite countertops in the kitchen and bath, modern fixtures, separate tub and showers and full size washer and dryer. We will also provide you with all kitchenware, linens, television, wifi, telephone, heating/cooling, electricity and everything else you need to be comfortable. Contact our office for a full inventory list. Guests will have access to the entire apartment. The building amenities include an expansive fitness center and private yoga/Pilates studio, resident lounge and gourmet kitchen, business center (copy, fax, scan wifi), library and fireplace, sports lounge with billiards table, private theater, golf simulator, coffee bar, 22,000 SF rooftop deck with outdoor fireplace, fire pit and lounge areas, heated pool, private cabanas with TV, outdoor kitchen/grills/bar, outdoor movie theater, dog park and pet wash, attached parking garage (extra fee), bike room and so much more. We professionally clean each property before your arrival, including every kitchen item and every linen in the property to ensure your complete satisfaction. We deliver 24-hour maintenance service to ensure your apartment stays in top condition for your entire stay. River North is surrounded by The Loop (business), Streeterville (retail) and Gold Coast (architecture and night life). Easy access to all public transportation. River North is known for it's restaurants, nightlife and upscale hotels. All doors provide cab access. The Clark Bus is at your doorstep. Other bus routes and all CTA Train routes are a couple blocks away. Easy access to major highways. Contact our office for detailed directions.
  • All-Inclusive Chicago Loop Apartment with River Views, Gym and Pool

    All-Inclusive Chicago Loop

    Chicago: Apartment
    • 1 BA
    • Sleeps 2
    • #233474
    $154 to $185 USD/night Credit Card Paypal Pet Friendly
    Enjoy stunning river views from your apartment before walking to work from this centrally located loop apartment. In your free time enjoy Michigan Avenue for shopping, as well as museums, restaurants and nightlife at your doorstep. The train, taxis, and buses are all accessible on the same block for even more convenience. Your apartment will include floor to ceiling windows with views of the Chicago river, designer kitchen with quartz countertops, white marble mosaic tile backsplash, stainless steel appliances, custom wood-plank flooring, polished natural stone vanities and tri-view medicine cabinets, custom closets with organizers, full sized-washer and dryer and controlled heating/air. We will also provide you with all kitchenware, linens, television, wireless internet, telephone, heating/cooling, electricity and everything else you need to be comfortable. This doorman building features an expansive two level outdoor sundeck including fire pits, private kitchens, lounge area, seating and grills, the building also features an expansive health club with towel service, stunning terrace, indoor pool and spa with retractable wall opening to sundeck, tech=bar with free printing, screening room, billiards room with TV and custom music system, lounge with floor-to-ceiling windows and another outdoor terrace overlooking the cityscape, bike room, heated parking (extra cost) and more. We deliver top customer service, and simple policies to meet your needs. Our clients enjoy month to month rental terms with just a 14-day notice to vacate and have the option to pay rent with any major credit card. Property is ready for our clients to move-in with just a suitcase. 31 Night Minimum Stay.
  • Luxury all-Inclusive Furnished River North Apartment

    Luxury all-Inclusive

    Chicago: Apartment in a complex
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #233206
    $154 to $236 USD/night Credit Card Paypal
    This location is surrounded by award winning restaurants and nightlife. Walk to the loop (business district), theater, magnificent mile, public transportation and river walk. The apartment is finished with granite countertops, stainless steel appliances, hardwood floors and modern furniture. The building includes resort level amenities such as a pool with private cabanas, fitness center and business center. If there is something that would make your stay more comfortable, just ask. We pride ourselves on delivering top customer satisfaction, each and every time. The apartment has wood flooring, stainless steel appliances, elegant granite countertops in the kitchen and bath, modern fixtures, separate tub and shower and full size washer and dryer. We will also provide you with all kitchenware, linens, television, wifi, telephone, heating/cooling, electricity and everything else you need to be comfortable. The building amenities include an expansive fitness center and private yoga/pilates studio, resident lounge and gourmet kitchen, business center (copy, fax, scan wifi), library and fireplace, sports lounge with billiards table, private theater, golf simulator, coffee bar, 22,000 sq foot rooftop deck with outdoor fireplace, fire pit and lounge areas, heated pool, private cabanas with TV, outdoor kitchen/grills/bar, outdoor movie theater, dog park and pet wash, attached parking garage (extra fee), bike room and so much more. We deliver 24-hour maintenance service to ensure your apartment stays in top condition for your entire stay. This building is surrounded by The Loop (business), Streeterville (retail) and Gold Coast (architecture and night life). Easy access to all public transportation. The River North area is known for it's restaurants, nightlife and upscale hotels. All doors provide cab access. The Clark Bus is at your doorstep. Other bus routes and all CTA Train routes are a couple blocks away. Easy access to major highways.
  • Luxury one Bedroom Rental

    Luxury one Bedroom Rental

    Chicago: The Loop: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 6
    • #224241
    $187 to $205 USD/night Credit Card Paypal Pet Friendly
    The minimum stay is 31 nights. This luxury building is close to work and offers top of the line amenities including an all-inclusive apartment. The LEED certified building offers a 24/7 door/security person, complimentary coffee/tea, 24/7 fitness center (cardio and weights), sauna, billiards table, poker table, entertainment room, board games, library, indoor and outdoor fireplace, business center (computers and printing), sky room (can be rented for parties), heated pool, outdoor grills, green dry cleaning and a dog run. Your apartment is equipped with all the comforts of home including stainless steel appliances (fridge, freezer, dishwasher, oven, stove top, garbage disposal), washer and dryer, flat screen TV, 140 cable channels, high-speed internet and a telephone with nationwide calling. All utilities are included including electricity, central heating/cooling, gas and water. We stock your kitchen with baking/cooking dishes and utensils, a coffee machine, teapot, and dishes. Your unit also includes all the linens and towels you will need in addition to a vacuum, hair dryer, iron and artwork. Dog friendly units are available upon request.
  • Luxury Studio Apartment Rental

    Luxury Studio Apartment

    Chicago: The Loop: Apartment
    • 1 BA
    • Sleeps 3
    • #224235
    $143 to $163 USD/night Credit Card Paypal Pet Friendly
    The minimum stay is 31 nights. This luxury building is close to work and offers top of the line amenities including an all-inclusive apartment. The LEED certified building offers a 24/7 door/security person, complimentary coffee/tea, 24/7 fitness center (cardio and weights), sauna, billiards table, poker table, entertainment room, board games, library, indoor and outdoor fireplace, business center (computers and printing), sky room (can be rented for parties), heated pool, outdoor grills, green dry cleaning and a dog run. Your apartment is equipped with all the comforts of home including stainless steel appliances (fridge, freezer, dishwasher, oven, stove top, garbage disposal), washer and dryer, flat screen TV, 140 cable channels, high-speed internet and a telephone with nationwide calling. All utilities are included including electricity, central heating/cooling, gas and water. We stock your kitchen with baking/cooking dishes and utensils, a coffee machine, teapot, and dishes. Your unit also includes all the linens and towels you will need in addition to a vacuum, hair dryer, iron and artwork. Dog friendly units are available upon request.
  • Luxury Jr. One Bedroom Rental

    Luxury Jr. One Bedroom

    Chicago: The Loop: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 5
    • #224239
    $154 to $179 USD/night Credit Card Paypal Pet Friendly
    The minimum stay is 31 nights. This luxury building is close to work and offers top of the line amenities including an all-inclusive apartment. The LEED certified building offers a 24/7 door/security person, complimentary coffee/tea, 24/7 fitness center (cardio and weights), sauna, billiards table, poker table, entertainment room, board games, library, indoor and outdoor fireplace, business center (computers and printing), sky room (can be rented for parties), heated pool, outdoor grills, green dry cleaning and a dog run. Your apartment is equipped with all the comforts of home including stainless steel appliances (fridge, freezer, dishwasher, oven, stove top, garbage disposal), washer and dryer, flat screen TV, 140 cable channels, high-speed internet and a telephone with nationwide calling. All utilities are included including electricity, central heating/cooling, gas and water. We stock your kitchen with baking/cooking dishes and utensils, a coffee machine, teapot, and dishes. Your unit also includes all the linens and towels you will need in addition to a vacuum, hair dryer, iron and artwork. Dog friendly units are available upon request.

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