Holiday rentals near Chestnut Mountain Resort
We found 630 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:1 Aug - 8 Aug
Image gallery for GORGEOUS LARGE HOME WITH HOT TUB! 4th NIGHT FREE!
1010 out of 10 rating
Exceptional
(170 reviews)
GORGEOUS LARGE HOME WITH HOT TUB! 4th NIGHT FREE!
Galena, IL
16% off
Price is NZ$15,492
NZ$15,492
NZ$2,213 per night
includes taxes & fees
Image gallery for Dubuque's Front Porch~Historic Charmer~Walk Downtn
1010 out of 10 rating
Exceptional
(22 reviews)
Dubuque's Front Porch~Historic Charmer~Walk Downtn
Dubuque, IA
8% off
Price is NZ$6,123
NZ$6,123
NZ$875 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
8% off
Price is NZ$3,800
NZ$3,800
NZ$543 per night
includes taxes & fees
Image gallery for Shady Haven - Tiny Home 1
1010 out of 10 rating
Exceptional
(12 reviews)
Shady Haven - Tiny Home 1
Bellevue, IA
12% off
Price is NZ$2,595
NZ$2,595
NZ$371 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 NZ$4,486
NZ$4,486
NZ$641 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 NZ$2,871
NZ$2,871
NZ$410 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 NZ$4,083
NZ$4,083
NZ$583 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
(14 reviews)
Private 50-acre Home Pet Friendly-Huge Greatroom-Firepit-Pond-Gameroom
Elizabeth, IL
8% off
Price is NZ$6,716
NZ$6,716
NZ$959 per night
includes taxes & fees
Image gallery for Historic, quiet, elegant, mix of modern & original
9.69.6 out of 10 rating
Exceptional
(77 reviews)
Historic, quiet, elegant, mix of modern & original
Dubuque, IA
17% off
Price is NZ$4,129
NZ$4,129
NZ$590 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
(138 reviews)
Dog friendly(with dog fee),Close to Downtown,Historic District,
Galena, IL
16% off
Price is NZ$3,622
NZ$3,622
NZ$517 per night
includes taxes & fees
Image gallery for 4 BR. Hot Tub. Pet Friendly. May Discounts!
9.49.4 out of 10 rating
Exceptional
(8 reviews)
4 BR. Hot Tub. Pet Friendly. May Discounts!
Galena, IL
8% off
Price is NZ$6,629
NZ$6,629
NZ$947 per night
includes taxes & fees
Image gallery for Ulysses Suites, Suite 201, 2 bedroom/2 bath, full kitchen and living room
1010 out of 10 rating
Exceptional
(6 reviews)
Ulysses Suites, Suite 201, 2 bedroom/2 bath, full kitchen and living room
Galena, IL
13% off
Price is NZ$6,365
NZ$6,365
NZ$909 per night
includes taxes & fees
Image gallery for Overlooking Historic Downtown Galena Suite #5
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Overlooking Historic Downtown Galena Suite #5
Galena, IL
8% off
Price is NZ$3,292
NZ$3,292
NZ$470 per night
includes taxes & fees
Image gallery for Secluded log cabin at the end of a quiet dead end lane
1010 out of 10 rating
Exceptional
(28 reviews)
Secluded log cabin at the end of a quiet dead end lane
Hazel Green, WI
13% off
Price is NZ$2,934
NZ$2,934
NZ$419 per night
includes taxes & fees
Image gallery for White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
1010 out of 10 rating
Exceptional
(18 reviews)
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails
Shullsburg, WI
17% off
Price is NZ$2,313
NZ$2,313
NZ$330 per night
includes taxes & fees
Image gallery for Tucked back on the 1st Tee of the South Course - cozy townhome.
1010 out of 10 rating
Exceptional
(34 reviews)
Tucked back on the 1st Tee of the South Course - cozy townhome.
Galena, IL
8% off
Price is NZ$2,463
NZ$2,463
NZ$352 per night
includes taxes & fees
Image gallery for Cozy and welcoming 3 Bed and 3 Bath with a hot tub and a game room is ready4u
1010 out of 10 rating
Exceptional
(74 reviews)
Cozy and welcoming 3 Bed and 3 Bath with a hot tub and a game room is ready4u
Galena, IL
8% off
Price is NZ$4,546
NZ$4,546
NZ$649 per night
includes taxes & fees
Image gallery for Dubuque Luxury “Hot Tub” Farmers Market
9.89.8 out of 10 rating
Exceptional
(42 reviews)
Dubuque Luxury “Hot Tub” Farmers Market
Dubuque, IA
16% off
Price is NZ$3,543
NZ$3,543
NZ$506 per night
includes taxes & fees
Image gallery for Annabel Lee Barn ~ A Getaway of Warmth & Charm!
1010 out of 10 rating
Exceptional
(13 reviews)
Annabel Lee Barn ~ A Getaway of Warmth & Charm!
Dubuque, IA
8% off
Price is NZ$7,101
NZ$7,101
NZ$1,014 per night
includes taxes & fees
Image gallery for Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View
1010 out of 10 rating
Exceptional
(29 reviews)
Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View
Galena, IL
6% off
Price is NZ$3,903
NZ$3,903
NZ$558 per night
includes taxes & fees
Image gallery for Rolling Hills Retreat
1010 out of 10 rating
Exceptional
(5 reviews)
Rolling Hills Retreat
Galena, IL
8% off
Price is NZ$5,781
NZ$5,781
NZ$826 per night
includes taxes & fees
Image gallery for New - Country Chic, Corner Unit, Dog Friendly - Only 12 Min to Downtown Galena
1010 out of 10 rating
Exceptional
(33 reviews)
New - Country Chic, Corner Unit, Dog Friendly - Only 12 Min to Downtown Galena
Galena, IL
6% off
Price is NZ$4,259
NZ$4,259
NZ$608 per night
includes taxes & fees
Image gallery for Escape to the country
1010 out of 10 rating
Exceptional
(9 reviews)
Escape to the country
Stockton, IL
18% off
Price is NZ$2,650
NZ$2,650
NZ$379 per night
includes taxes & fees
Image gallery for Spring Creek Sanctuary
9.49.4 out of 10 rating
Exceptional
(12 reviews)
Spring Creek Sanctuary
Galena, IL
8% off
Price is NZ$2,665
NZ$2,665
NZ$381 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
Villa
Chalet
Find the best place to stay - Chestnut Mountain Resort
New Owners- 3 BR 3 BA Getaway - Galena Territory & Owners' Club Privileges
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
155 reviews(155 reviews)
Freshly Updated!
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
89 reviews(89 reviews)
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Sleeps 14 · 5 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
Updated Retreat w/ Golf Course & Wildlife Views!
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
#Fido Friendly! Resort Core Location! Private Outdoor Hot Tub & Fire Pit!
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
107 reviews(107 reviews)
Inviting Home with Stunning Golf Course View - Fireplace, Hot Tub & Fire Pit
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
58 reviews(58 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