Galena Historic District holiday rentals

We found 80 holiday rentals — enter your dates for availability

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October 2025

November 2025

Discover a selection of 6 homes and other holiday rentals in Galena Historic District that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and garden. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Galena Historic District

Showing deals for:2 Jan - 9 Jan

Exceptional

(72 reviews)

Elle & Beck's Second Floor Suite Overlooking Historic Main Street In Galena, IL

Galena, IL

17% off

for 7 nights, 1 apartment

AU$668 per night

includes taxes & fees

Galena Vacation Rental | 3BR | 1.5BA | 2 Stories | 1,500 Sq Ft

Exceptional

(51 reviews)

'The FiveTen Federal' - Downtown Galena Gem!

Galena, IL

11% off

for 7 nights, 1 home

AU$583 per night

includes taxes & fees

Address sign and gate to entrance of apartment.

Exceptional

(12 reviews)

One Bedroom Apartment Overlooking Main Street with One Designated Parking Spot

Galena, IL

8% off

for 7 nights, 1 apartment

AU$342 per night

includes taxes & fees

Exceptional

(28 reviews)

Two Story Suite Overlooking Historic Main Street Galena, IL. Sleeps 16!

Galena, IL

17% off

for 7 nights, 1 apartment

AU$1,739 per night

includes taxes & fees

Front of the house with adjacent shared-driveway

Exceptional

(92 reviews)

New Listing! Charming home two blocks from Galena Main St with deck and parking

Galena, IL

17% off

for 7 nights, 1 home

AU$539 per night

includes taxes & fees

Exceptional

(86 reviews)

The Loft Suite Sleeps 10! Located overlooking Main Street in downtown Galena, IL

Galena, IL

17% off

for 7 nights, 1 home

AU$835 per night

includes taxes & fees

Exceptional

(149 reviews)

Dog friendly(with dog fee),Close to Downtown,Historic District,

Galena, IL

17% off

for 7 nights, 1 cottage

AU$418 per night

includes taxes & fees

Exceptional

(33 reviews)

Beautiful Suite in Galena B&B With King Bed, Private Bath, Fireplace, Wet Bar

Galena, IL

9% off

for 7 nights, 1 room

AU$311 per night

includes taxes & fees

Exceptional

(149 reviews)

Luxurious Suite in Galena B&B, King bed, Private Bath, Fireplace & Wet Bar

Galena, IL

13% off

for 7 nights, 1 room

AU$274 per night

includes taxes & fees

Address sign and entrance to stairs leading down to the apartment

Exceptional

(8 reviews)

Two Bedroom Apartment Overlooking Main Street with One Designated Parking Spot

Galena, IL

8% off

for 7 nights, 1 apartment

AU$417 per night

includes taxes & fees

Exceptional

(11 reviews)

Ulysses Suites, Suite 201, 2 bedroom/2 bath, full kitchen and living room

Galena, IL

13% off

for 7 nights, 1 apartment

AU$780 per night

includes taxes & fees

Exceptional

(8 reviews)

Come stay in this Circa1845 Historical Building located in Downtown Galena.

Galena, IL

8% off

for 7 nights, 1 apartment

AU$234 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Galena Historic District

Old Market House

Find the best place to stay - Galena Historic District

Premier Host

Downtown Galena Luxury Rentals Suite 3 Parking New

Sleeps 4 · 1 bedroom · 1 bathroom

10 Min Walk to Main St., Updated 1840s Historic Home, Stocked Kitchen, W/D,

Sleeps 6 · 3 bedrooms · 2 bathrooms

Premier Host

View from Quality Hill overlooking historic district, quick walk to downtown

Sleeps 6 · 3 bedrooms · 3 bathrooms

Premier Host

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

Sleeps 4 · 1 bedroom · 1 bathroom

Premier Host

Cider Sips & Cozy Nights @ Gazette Suites on Commerce St! Dedicated Parking!

Sleeps 5 · 2 bedrooms · 2 bathrooms

Premier Host

Brisk Fall days on Bench St – Steps from Shopping, Dining & Turner Hall!

Sleeps 8 · 3 bedrooms · 1+ bathroom

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Galena Historic District?

The most desirable types of holiday homes in Galena Historic District are houses. After something a little different? Stayz offers a variety of options to match our guests' unique needs, so you'll see properties in lots of sizes and shapes. The perfect fit is waiting for you — find yours today.

How much does it cost to rent a holiday home in Galena Historic District?

Several factors affect what you'll pay for your holiday home in Galena Historic District, like the type of property, length of stay and season. Still, all of our holiday homes have one thing in common — exceptional value. Simply enter your travel dates to find your home away from home.

How much does it cost to rent a beach house in Galena Historic District?

The average price for a holiday home close to the beach in Galena Historic District depends on when you're travelling and the size and type of property you're looking for. Find prices easily and quickly on Stayz by entering your travel dates and destination. Then use the handy filters to pick the number of bedrooms and amenities that you need, like WiFi, a pool and air conditioning.

Are there pet-friendly holiday homes in Galena Historic District?

With 11 properties that host four-legged guests, your little buddy can join in the fun on your Galena Historic District getaway. Use our filter tool to browse our pet-friendly holiday homes and find your pawfect digs on Stayz.

What are popular home amenities in Galena Historic District?

When it comes to home amenities that guests are on the lookout for in Galena Historic District, a garden, a fireplace and a barbecue grill are the most popular. With Stayz holiday homes, there are options to fit your style and taste, whether you're going on a trip with friends, relatives or even pets.

Are there large group holiday homes in Galena Historic District?

Galena Historic District has three holiday homes that can host 10 or more people. These stays come with the space and privacy you need to share good times with family and friends.

Are there holiday homes in Galena Historic District that welcome kids?

Galena Historic District has 11 family-friendly holiday homes to choose from. And finding a stay that welcomes kiddos is super easy with our "Properties good for families" filter. On top of having the whole place to yourselves, you'll get access to amenities and perks such as dining rooms, kitchens and pools.

What are the top attractions for families in Galena Historic District?

Keeping the kiddos entertained during your Galena Historic District holiday is child's play with these awesome family-friendly attractions:

Dowling House
Galena-Jo Daviess County History Museum
Belvedere Mansion

Are there holiday homes with WiFi in Galena Historic District?

Galena Historic District has five holiday homes with WiFi, so you can stay connected during your trip. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Stayz homes make it a breeze to get online.

How can I find holiday homes with air conditioning in Galena Historic District?

Select your travel dates and then use the filters to locate holiday homes with ac in Galena Historic District on Stayz. With 11 air-conditioned properties available here, you can enjoy a cool and comfy break.

How old do you have to be to rent a holiday home in Galena Historic District?

The minimum age permitted can differ across properties on Stayz, so be sure to look at the rules of the holiday home in Galena Historic District you want. But normally, it's 16, 18 or 21.

How long can I rent a holiday home in Galena Historic District for?

It's really down to the Galena Historic District property. To view a list of options offering extended stays, just enter your dates and number of people into Stayz's search page. You can look forward to having the property to yourself, along with comforts such as a fully-equipped kitchen and an outdoor space where the kids can run and play. Be on the lookout for long-term stays that offer discounted weekly or monthly prices.