Holiday rentals near Chestnut Mountain Resort
We found 625 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:8 Aug - 15 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
17% off
Price is NZ$14,957
NZ$14,957
NZ$2,137 per night
includes taxes & fees
Image gallery for Modern Hideaway Hot tub Great for large groups!
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Modern Hideaway Hot tub Great for large groups!
Galena, IL
8% off
Price is NZ$7,690
NZ$7,690
NZ$1,099 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
(42 reviews)
The Downtown House - 1820s home steps from Main Street in downtown Galena
Galena, IL
13% off
Price is NZ$4,975
NZ$4,975
NZ$711 per night
includes taxes & fees
Image gallery for Dubuque's Front Porch~Historic Charmer~Walk Downtn
1010 out of 10 rating
Exceptional
(23 reviews)
Dubuque's Front Porch~Historic Charmer~Walk Downtn
Dubuque, IA
8% off
Price is NZ$5,881
NZ$5,881
NZ$840 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$2,690
NZ$2,690
NZ$384 per night
includes taxes & fees
Image gallery for Treehouse: Fall views with your crew! Firepit! Cozy, Secluded, + Spacious.
1010 out of 10 rating
Exceptional
(14 reviews)
Treehouse: Fall views with your crew! Firepit! Cozy, Secluded, + Spacious.
Galena, IL
8% off
Price is NZ$6,192
NZ$6,192
NZ$885 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$4,438
NZ$4,438
NZ$634 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$2,837
NZ$2,837
NZ$405 per night
includes taxes & fees
Image gallery for Secluded Wooded Retreat 6- BR, W/Pond, Hot Tub, Sleeps 12+!!
9.49.4 out of 10 rating
Exceptional
(120 reviews)
Secluded Wooded Retreat 6- BR, W/Pond, Hot Tub, Sleeps 12+!!
Galena, IL
20% off
Price is NZ$6,922
NZ$6,922
NZ$989 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
(15 reviews)
Private 50-acre Home Pet Friendly-Huge Greatroom-Firepit-Pond-Gameroom
Elizabeth, IL
8% off
Price is NZ$6,623
NZ$6,623
NZ$946 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
16% off
Price is NZ$4,195
NZ$4,195
NZ$599 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
(90 reviews)
Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing
Galena, IL
12% off
Price is NZ$3,873
NZ$3,873
NZ$553 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$3,589
NZ$3,589
NZ$513 per night
includes taxes & fees
Image gallery for The Linden; New construction Galena Retreat w/ hot tub & pool table
1010 out of 10 rating
Exceptional
(13 reviews)
The Linden; New construction Galena Retreat w/ hot tub & pool table
Galena, IL
8% off
Price is NZ$11,920
NZ$11,920
NZ$1,703 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$6,528
NZ$6,528
NZ$933 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$6,283
NZ$6,283
NZ$898 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$2,901
NZ$2,901
NZ$414 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$3,256
NZ$3,256
NZ$465 per night
includes taxes & fees
Image gallery for 233 Main Street Penthouse
1010 out of 10 rating
Exceptional
(32 reviews)
233 Main Street Penthouse
Dubuque, IA
16% off
Price is NZ$4,622
NZ$4,622
NZ$660 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$2,283
NZ$2,283
NZ$326 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$2,433
NZ$2,433
NZ$348 per night
includes taxes & fees
Image gallery for Dubuque Luxury “Hot Tub” Farmers Market
9.89.8 out of 10 rating
Exceptional
(43 reviews)
Dubuque Luxury “Hot Tub” Farmers Market
Dubuque, IA
16% off
Price is NZ$3,606
NZ$3,606
NZ$515 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
(75 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$4,496
NZ$4,496
NZ$642 per night
includes taxes & fees
Image gallery for Stunning on South Golf Course; Golden Tee, Patio TV, Fire Pit, Hot Tub & More!!
1010 out of 10 rating
Exceptional
(95 reviews)
Stunning on South Golf Course; Golden Tee, Patio TV, Fire Pit, Hot Tub & More!!
Galena, IL
6% off
Price is NZ$8,801
NZ$8,801
NZ$1,257 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
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
90 reviews(90 reviews)
Updated Retreat w/ Golf Course & Wildlife Views!
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Inviting Home with Stunning Golf Course View - Fireplace, Hot Tub & Fire Pit
Sleeps 6 · 2 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
58 reviews(58 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)
2 Bedroom, 2 Bath Hot Tub home in the Galena Territory
Sleeps 4 · 2 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
177 reviews(177 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