Two hot air balloons on a snowy field with a forest in the background.

Jo Daviess County Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Jo Daviess County holiday rentals

Interior

1. Two Bedroom Apartment Overlooking Main Street with One Designated Parking Spot

Two Bedroom Apartment Overlooking Main Street with One Designated Parking Spot
Galena Historic District
9.8 out of 10, Exceptional, (15 reviews)
"Parking was great"
United States
Jennifer
The price is HK$1,757
HK$2,984 total
includes taxes & fees
13 Sept - 14 Sept
Two Bedroom Apartment Overlooking Main Street with One Designated Parking Spot
Exterior

2. An Artistic retreat in the heart of downtown Galena

An Artistic retreat in the heart of downtown Galena
Galena
9.8 out of 10, Exceptional, (31 reviews)
"Very nice space conveniently located to enjoy downtown Galena. Host was helpful and available for our stay."
United States
Rob W.
The price is HK$1,441
HK$1,824 total
includes taxes & fees
14 Sept - 15 Sept
An Artistic retreat in the heart of downtown Galena
Living area

3. Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC

Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC
Galena Historic District
9.4 out of 10, Exceptional, (22 reviews)
"Great location for a down town galena stay. "
United States
Christian R.
The price is HK$1,098
HK$1,803 total
includes taxes & fees
15 Sept - 16 Sept
Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC
Exterior

4. North Woods Lodge Vibes•Hot Tub+Fire Pit•3 Seasons Room•Galena Territory Retreat

North Woods Lodge Vibes•Hot Tub+Fire Pit•3 Seasons Room•Galena Territory Retreat
The Galena Territory
10.0 out of 10, Exceptional, (271 reviews)
"We had a wonderful stay, enjoyed the location being close to Galena but still remote. "
United States
Megan C.
The price is HK$2,477
HK$5,409 total
includes taxes & fees
13 Sept - 14 Sept
North Woods Lodge Vibes•Hot Tub+Fire Pit•3 Seasons Room•Galena Territory Retreat
Interior

5. Elle & Becks loft Suite

Elle & Becks loft Suite
Galena Historic District
10.0 out of 10, Exceptional, (102 reviews)
"Cleanest I have ever stayed in. Perfect location for shopping and eating. Beds were super comfortable."
United States
April V.
The price is HK$3,376
HK$5,823 total
includes taxes & fees
20 Sept - 21 Sept
Elle & Becks loft Suite
Terrace/patio

6. Hot Tub 2-BDRM, 2 full bath all comforts of home in Galena countryside

Hot Tub 2-BDRM, 2 full bath all comforts of home in Galena countryside
Galena
10.0 out of 10, Exceptional, (46 reviews)
"We all fell in love with this place! It was super clean, comfortable, had everything we needed! The sunset from the patio was spectacular! We highly recommend to anyone staying in the area and hope to be back!"
United States
Amy R.
The price is HK$2,188
HK$3,946 total
includes taxes & fees
27 Sept - 28 Sept
Hot Tub 2-BDRM, 2 full bath all comforts of home in Galena countryside
Terrace/patio

7. One Bedroom Apartment Overlooking Main Street with One Designated Parking Spot

One Bedroom Apartment Overlooking Main Street with One Designated Parking Spot
Galena Historic District
10.0 out of 10, Exceptional, (33 reviews)
"We loved our weekend stay, great vintage apartment with ideal location."
United States
Robert S.
The price is HK$1,052
HK$2,103 total
includes taxes & fees
15 Sept - 16 Sept
One Bedroom Apartment Overlooking Main Street with One Designated Parking Spot
Outdoor dining

8. Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.

Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.
Galena
10.0 out of 10, Exceptional, (105 reviews)
"Cleanliness and loved the hot tub!"
United States
Adanary
The price is HK$2,745
HK$4,423 total
includes taxes & fees
6 Oct - 7 Oct
Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.
Outdoor spa tub

9. The Nook: Downtown Galena Cottage, BRAND NEW LUX HOT TUB & fire pit!

The Nook: Downtown Galena Cottage, BRAND NEW LUX HOT TUB & fire pit!
Galena
10.0 out of 10, Exceptional, (152 reviews)
"We really enjoyed our stay here! The place was clean, comfortable, and felt very safe. It was the perfect home base for our weekend trip to Galena, and the location made it easy to explore the area. We’d definitely stay here again."
United States
Kulsoom A.
The price is HK$2,060
HK$4,559 total
includes taxes & fees
16 Sept - 17 Sept
The Nook: Downtown Galena Cottage, BRAND NEW LUX HOT TUB & fire pit!
Private kitchen

10. Elle & Becks Second Floor Suite

Elle & Becks Second Floor Suite
Galena Historic District
10.0 out of 10, Exceptional, (79 reviews)
"This was the second time I have stayed here and it is the perfect place to comfortably bag out and connect with loved ones. "
United States
mary r.
The price is HK$3,376
HK$5,986 total
includes taxes & fees
23 Sept - 24 Sept
Elle & Becks Second Floor Suite
Private kitchen

11. Cozy well-appointed Guest Suite on a grass airstrip

Cozy well-appointed Guest Suite on a grass airstrip
Hanover
10.0 out of 10, Exceptional, (19 reviews)
"Both myself and Winston really enjoyed our recent stay. I got to experience "fancy toilet" :) and Winston could roam around the property. Condo was super clean and very nicely decorated. I wish we stayed 2 nights as originally planned..."
United States
Don
The price is HK$1,686
HK$2,037 total
includes taxes & fees
13 Sept - 14 Sept
Cozy well-appointed Guest Suite on a grass airstrip
Exterior

12. 3 Bed, 2 Bath Spacious Galena Home

3 Bed, 2 Bath Spacious Galena Home
The Galena Territory
10.0 out of 10, Exceptional, (2 reviews)
"Very clean!"
United States
Leah D.
3 Bed, 2 Bath Spacious Galena Home
Pool

13. Fall in Galena - Golf View - 2 King Beds - Near Trails, Indoor Pool & Downtown

Fall in Galena - Golf View - 2 King Beds - Near Trails, Indoor Pool & Downtown
The Galena Territory
10.0 out of 10, Exceptional, (97 reviews)
"Place was amazing we loved it!!"
United States
Amanda S.
The price is HK$727
HK$2,084 total
includes taxes & fees
16 Sept - 17 Sept
Fall in Galena - Golf View - 2 King Beds - Near Trails, Indoor Pool & Downtown
Pool

14. Golf Villa - Pool Access + Private Deck

Golf Villa - Pool Access + Private Deck
The Galena Territory
9.8 out of 10, Exceptional, (88 reviews)
"Awesome place, close to everything that’s near and nice amen"
United States
Genaro
The price is HK$1,019
HK$2,302 total
includes taxes & fees
15 Sept - 16 Sept
Golf Villa - Pool Access + Private Deck
Pool

15. Picture Perfect Galena Getaway on Golf Course | 4 Bed 4 Bath | Hot Tub & FirePit

Picture Perfect Galena Getaway on Golf Course | 4 Bed 4 Bath | Hot Tub & FirePit
The Galena Territory
10.0 out of 10, Exceptional, (319 reviews)
"Love this property!Celebrated my Mom's bday with the family and we were so comfortable in this house.Modern finishes and appliances, very clean, alongside a golf course and easy access to everything. Plus spacious and great amenities!"
United States
Caroline F.
The price is HK$2,419
HK$5,127 total
includes taxes & fees
13 Sept - 14 Sept
Picture Perfect Galena Getaway on Golf Course | 4 Bed 4 Bath | Hot Tub & FirePit
Exterior

16. Spacious 3BR*Ensuites | Hot Tub*Fire Pit*Game Room*Coffee Bar*Stunning Sunsets!

Spacious 3BR*Ensuites | Hot Tub*Fire Pit*Game Room*Coffee Bar*Stunning Sunsets!
The Galena Territory
10.0 out of 10, Exceptional, (67 reviews)
"Great home with beautiful scenic, country views. It was very quiet and relaxing - perfect for three adult couples. It had everything we needed for a long weekend stay."
United States
Tracy B.
The price is HK$1,680
HK$3,991 total
includes taxes & fees
13 Sept - 14 Sept
Spacious 3BR*Ensuites | Hot Tub*Fire Pit*Game Room*Coffee Bar*Stunning Sunsets!
Property grounds

17. 1850 Cabin Home - Large Backyard- 22' Movie Screen-Family-Event - Travelers

1850 Cabin Home - Large Backyard- 22' Movie Screen-Family-Event - Travelers
East Dubuque
9.6 out of 10, Exceptional, (44 reviews)
"Great property, plenty of room for everyone in our group to stay. A well equipped kitchen and the yard space (weather permitting) were highlights. Good location minutes away from activities across the river as well."
United States
Cody H.
The price is HK$1,882
HK$2,618 total
includes taxes & fees
12 Sept - 13 Sept
1850 Cabin Home - Large Backyard- 22' Movie Screen-Family-Event - Travelers
Dining

18. Lovely King Studio walking distance to downtown

Lovely King Studio walking distance to downtown
Galena
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and the hosts had excellent communication with us."
United States
Shawn M.
The price is HK$1,523
HK$1,899 total
includes taxes & fees
14 Sept - 15 Sept
Lovely King Studio walking distance to downtown
Exterior

19. The Bogey at Oak Glen | Walk to Eagle Ridge Golf | 2 King Ensuites | Fireplace

The Bogey at Oak Glen | Walk to Eagle Ridge Golf | 2 King Ensuites | Fireplace
The Galena Territory
10.0 out of 10, Exceptional, (61 reviews)
"It was a nice location and a nice property. The owner was informative and readily available. It was a great stay!"
United States
Faith N.
The price is HK$2,021
HK$3,669 total
includes taxes & fees
24 Sept - 25 Sept
The Bogey at Oak Glen | Walk to Eagle Ridge Golf | 2 King Ensuites | Fireplace
Interior

20. Galena Retreat: Shopping, Owners Club & Skiing!

Galena Retreat: Shopping, Owners Club & Skiing!
3.5 star property
The Galena Territory
10.0 out of 10, Exceptional, (2 reviews)
"Love the place ！highly recommended ! Will be back ……"
United States
Sing
The price is HK$980
HK$2,674 total
includes taxes & fees
6 Oct - 7 Oct
Galena Retreat: Shopping, Owners Club & Skiing!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jo Daviess County Hotel Reviews

Chestnut Mountain Resort

Chestnut Mountain Resort

8/10 Good
"The stay was enjoyable! The view was beautiful! Food and service was great! The ac unit needed a filter change or cleaning, it didnt run well, tv remote was broken and the refrigerator was not working well. Otherwise, I will be back with my family!"
Kelly 2-night trip
Posted 16 hours ago
Chestnut Mountain Resort