Holiday rentals in Galena

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Top-rated holiday rentals in Galena

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Flat in Galena
Farmhouse Style Apt, Steps from Main St, Parking!
Nestled in the heart of historical downtown Galena, our quiet and private apartment suite is only steps away from shopping, dining, entertainment and everything Galena has to offer. Wake up to a full tea and coffee bar and make yourself at home as you wind down at the end of the day. As you walk out and down the stone stairway, you will find yourself in the middle of Main Street! A reserved, off street, parking space is included with your stay! We fully clean and disinfect between stays.
31 May – 7 Jun
$122 SGD per night
4.83 out of 5 average rating, 453 reviews
Guest favourite
Flat in Galena
Ulysses Suites, Suite 202
Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213-217 S. Main Street. The location is walking distance to all the best restaurants and shops. We have 7 suites and a beautiful lobby that are modern and luxurious, with lots of historical character and texture as a nod to its previous existence as the Grant Hotel from 1895 to 1933. Suite 202 is a gorgeous studio with a huge window seat looking over Main Street.
2–9 Nov
$284 SGD per night
4.98 out of 5 average rating, 229 reviews
Guest favourite
Flat in Galena
Downtown Gem for Two
Newly remodeled downtown apartment right in the middle of town. New furnishings, office nook with desk, full size kitchen and appliances, smart tv, free wifi, large open living space with private bedroom and bath. Very clean. Adjacent shared deck with table and chairs is available for use. This is a second floor apartment in the back of Simply Elegant Boutique so there are 17 steps to get to it from the outside. *Rest easy, every surface and door knob is disinfected after each stay.
26 Aug – 2 Sep
$165 SGD per night
4.94 out of 5 average rating, 294 reviews

Popular amenities for Galena holiday rentals

Stay near Galena's top sights

Blaum Bros. Distilling Co.28 locals recommend
Grant Park11 locals recommend
Vinny Vanucchi's20 locals recommend
Durty Gurt's13 locals recommend
Fried Green Tomatoes49 locals recommend
DeSoto House Hotel7 locals recommend

Other great holiday rentals in Galena

Guest favourite
Cabin in Durango
Cozy Cabin by the Pond
6–13 Dec
$153 SGD per night
5.0 out of 5 average rating, 231 reviews
Guest favourite
Cabin in Hazel Green
Romantic one bedroom cabin with indoor fireplace
20–27 Sep
$237 SGD per night
5.0 out of 5 average rating, 109 reviews
Guest favourite
Treehouse in Galena
Octagon house in woods- Hot tub, fireplace, pool
25 Nov – 2 Dec
$407 SGD per night
4.98 out of 5 average rating, 50 reviews
Guest favourite
Cabin in Galena
Hot tub! In/Outdoor fires-Game Room-3 King beds!
9–16 Feb
$695 SGD per night
5.0 out of 5 average rating, 26 reviews
Guest favourite
Cabin in Galena
Amenities Galore *Fantastic Location* Top Rental
31 Jan – 7 Feb
$722 SGD per night
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Shullsburg
The Car Wash Inn A Unique Stay
13–20 Oct
$137 SGD per night
5.0 out of 5 average rating, 80 reviews
Guest favourite
Home in Galena
The Owl House
25 Nov – 2 Dec
$488 SGD per night
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Galena
* 10 min Walk to Main Street*Stocked kitchen*
11–18 Jan
$211 SGD per night
4.99 out of 5 average rating, 76 reviews
Guest favourite
Home in Galena
Cozy Galena Townhome
22–29 May
$256 SGD per night
5.0 out of 5 average rating, 34 reviews
Guest favourite
Home in Galena
Serene | King bed | Fireplace | Indoor pool | Golf
20–27 Jun
$192 SGD per night
4.99 out of 5 average rating, 79 reviews
Guest favourite
Home in Dubuque
Home by the River
5–12 Jun
$158 SGD per night
5.0 out of 5 average rating, 48 reviews
Guest favourite
Cabin in Galena
Treehouse: NEWLY Remodeled! Spacious + Secluded!
3–10 Oct
$426 SGD per night
5.0 out of 5 average rating, 15 reviews

Quick stats about holiday rentals in Galena

Total rentals

130 properties

Rentals with dedicated workspaces

50 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

17K reviews

Nightly prices starting at

$67 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Jo Daviess County
  5. Galena