Holiday rentals near Chestnut Mountain Resort
We found 647 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals near Chestnut Mountain Resort that provide the perfect home base for your trip. Whether you're going on holiday with family or friends, holiday homes have the amenities that you need and want for your stay, including parking and a TV. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Chestnut Mountain Resort
Showing deals for:19 Sept - 26 Sept
Image gallery for GORGEOUS LARGE HOME WITH HOT TUB! 4th NIGHT FREE!
1010 out of 10 rating
Exceptional
(172 reviews)
GORGEOUS LARGE HOME WITH HOT TUB! 4th NIGHT FREE!
Galena, IL
17% off
Price is AU$11,604
AU$11,604
AU$1,658 per night
includes taxes & fees
Image gallery for Beautiful Log Cabin with Fireplace, Fire Pit, Hot Tub & Wifi
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Beautiful Log Cabin with Fireplace, Fire Pit, Hot Tub & Wifi
Galena, IL
8% off
Price is AU$6,969
AU$6,969
AU$996 per night
includes taxes & fees
Image gallery for The Downtown House - 1820s home steps from Main Street in downtown Galena
1010 out of 10 rating
Exceptional
(44 reviews)
The Downtown House - 1820s home steps from Main Street in downtown Galena
Galena, IL
13% off
Price is AU$4,548
AU$4,548
AU$650 per night
includes taxes & fees
Image gallery for Secluded Country Dream with all the Fun!
1010 out of 10 rating
Exceptional
(15 reviews)
Secluded Country Dream with all the Fun!
Galena, IL
6% off
Price is AU$8,576
AU$8,576
AU$1,225 per night
includes taxes & fees
Image gallery for The Gathering Place- Modern, Spacious, 6 Bedrooms
1010 out of 10 rating
Exceptional
(65 reviews)
The Gathering Place- Modern, Spacious, 6 Bedrooms
Galena, IL
8% off
Price is AU$12,493
AU$12,493
AU$1,785 per night
includes taxes & fees
Image gallery for Relaxing Townhouse Downtown Dubuque
1010 out of 10 rating
Exceptional
(22 reviews)
Relaxing Townhouse Downtown Dubuque
Dubuque, IA
8% off
Price is AU$3,509
AU$3,509
AU$501 per night
includes taxes & fees
Image gallery for Peaceful Retreat in Galena Country Jo Daviess County
1010 out of 10 rating
Exceptional
(16 reviews)
Peaceful Retreat in Galena Country Jo Daviess County
Apple River, IL
9% off
Price is AU$3,427
AU$3,427
AU$490 per night
includes taxes & fees
Image gallery for Galena Territory, Newly updated Single family home
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Galena Territory, Newly updated Single family home
Galena, IL
12% off
Price is AU$4,054
AU$4,054
AU$579 per night
includes taxes & fees
Image gallery for Fantastic Golf Views From This Single Family Home!
9.89.8 out of 10 rating
Exceptional
(95 reviews)
Fantastic Golf Views From This Single Family Home!
Galena, IL
16% off
Price is AU$2,621
AU$2,621
AU$374 per night
includes taxes & fees
Image gallery for Private 50-acre Home Pet Friendly-Huge Greatroom-Firepit-Pond-Gameroom
1010 out of 10 rating
Exceptional
(16 reviews)
Private 50-acre Home Pet Friendly-Huge Greatroom-Firepit-Pond-Gameroom
Elizabeth, IL
8% off
Price is AU$6,854
AU$6,854
AU$979 per night
includes taxes & fees
Image gallery for Historic, quiet, elegant, mix of modern & original
9.69.6 out of 10 rating
Exceptional
(78 reviews)
Historic, quiet, elegant, mix of modern & original
Dubuque, IA
17% off
Price is AU$3,775
AU$3,775
AU$539 per night
includes taxes & fees
Image gallery for Luxuary 4br, 4.5 Bath Galena Territory Rental With Hot Tub & Pool Table
1010 out of 10 rating
Exceptional
(160 reviews)
Luxuary 4br, 4.5 Bath Galena Territory Rental With Hot Tub & Pool Table
Galena, IL
8% off
Price is AU$6,704
AU$6,704
AU$958 per night
includes taxes & fees
Image gallery for 3 Bedroom - 3 Bath in the Heart of the Galena Territory Amenity Accessibility
1010 out of 10 rating
Exceptional
(113 reviews)
3 Bedroom - 3 Bath in the Heart of the Galena Territory Amenity Accessibility
Galena, IL
19% off
Price is AU$4,612
AU$4,612
AU$659 per night
includes taxes & fees
Image gallery for Overlooking Historic Downtown Galena Suite #3
1010 out of 10 rating
Exceptional
(5 reviews)
Overlooking Historic Downtown Galena Suite #3
Galena, IL
8% off
Price is AU$3,023
AU$3,023
AU$432 per night
includes taxes & fees
Image gallery for The Loft Suite Sleeps 10! Located overlooking Main Street in downtown Galena, IL
1010 out of 10 rating
Exceptional
(84 reviews)
The Loft Suite Sleeps 10! Located overlooking Main Street in downtown Galena, IL
Galena, IL
17% off
Price is AU$6,130
AU$6,130
AU$876 per night
includes taxes & fees
Image gallery for New Listing - Secluded retreat, Tree-top Views, Hot tub
1010 out of 10 rating
Exceptional
(8 reviews)
New Listing - Secluded retreat, Tree-top Views, Hot tub
Galena, IL
8% off
Price is AU$3,966
AU$3,966
AU$567 per night
includes taxes & fees
Image gallery for Near golf courses and amenities!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Near golf courses and amenities!
Galena, IL
8% off
Price is AU$2,916
AU$2,916
AU$417 per night
includes taxes & fees
Image gallery for Dog friendly(with dog fee),Close to Downtown,Historic District,
9.49.4 out of 10 rating
Exceptional
(140 reviews)
Dog friendly(with dog fee),Close to Downtown,Historic District,
Galena, IL
16% off
Price is AU$3,270
AU$3,270
AU$467 per night
includes taxes & fees
Image gallery for Galena's Premier Lakeview 6 BR/5.5 BA Executive Home; Can rent as 4, 5 or 6 BR
9.89.8 out of 10 rating
Exceptional
(60 reviews)
Galena's Premier Lakeview 6 BR/5.5 BA Executive Home; Can rent as 4, 5 or 6 BR
Galena, IL
8% off
Price is AU$12,710
AU$12,710
AU$1,816 per night
includes taxes & fees
Image gallery for New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!
1010 out of 10 rating
Exceptional
(6 reviews)
New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!
Apple River, IL
16% off
Price is AU$6,566
AU$6,566
AU$938 per night
includes taxes & fees
Image gallery for Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing
9.89.8 out of 10 rating
Exceptional
(91 reviews)
Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing
Galena, IL
12% off
Price is AU$2,989
AU$2,989
AU$427 per night
includes taxes & fees
Image gallery for Beautiful 3Bed 4.5Bath Cabin w/ Bonus Room - Near Trails and Lake
1010 out of 10 rating
Exceptional
(5 reviews)
Beautiful 3Bed 4.5Bath Cabin w/ Bonus Room - Near Trails and Lake
Galena, IL
6% off
Price is AU$6,959
AU$6,959
AU$994 per night
includes taxes & fees
Image gallery for Rocky Waters Vineyard/Winery Guest House Hanover IL
9.89.8 out of 10 rating
Exceptional
(92 reviews)
Rocky Waters Vineyard/Winery Guest House Hanover IL
Hanover, IL
8% off
Price is AU$5,257
AU$5,257
AU$751 per night
includes taxes & fees
Image gallery for Golf Villa in the heart of The Galena Territory
1010 out of 10 rating
Exceptional
(198 reviews)
Golf Villa in the heart of The Galena Territory
Galena, IL
8% off
Price is AU$1,863
AU$1,863
AU$266 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Chestnut Mountain Resort
Townhome - Indoor Pool, Arcade, Hiking, Skiing
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Updated Retreat w/ Golf Course & Wildlife Views!
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
Two Bedroom + LOFT, Cozy Golf View Villa, Fast WiFi
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
61 reviews(61 reviews)
Lakeside is a spacious, flowing home located on the north shores of Lake Galena
Sleeps 12 · 5 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
103 reviews(103 reviews)
Summer Break @ Poplar Ridge! Amazing Golf Course View with Access 2 Pools!
Sleeps 4 · 1 bedroom · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
373 reviews(373 reviews)
On The Golf Course, Outdoor Kitchen, Hot Tub and So Much More!
Sleeps 14 · 6 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
144 reviews(144 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value