Holiday rentals in Galena

4.82 out of 5 average rating, 631 reviews

Loft in Galena

Fireplace Apartment Main Street Galena

My apartment is located right on Galena's historic main street also known as the Helluvahalfmile. The apartment has just been renovated though it is on the original listing for the apartment. It is now much better than before! There are restaurants and dining, family-friendly activities, and nightlife just feet away. You’ll love my place because of it's location, the ambiance, people and the Galena main street life. You are right above my restaurant too, which serves coffee, breakfast and lunch!

4.99 out of 5 average rating, 345 reviews

Guest house in Galena

The Guest House - Private and All Yours

*Some revenue from your stay will go to SPLC, ACLU, and other progressive causes* Enjoy the cozy comforts of this renovated studio in Galena's historic district. The building is yours for your stay, with driveway parking onsite. We've made this a welcoming space for respectful travelers of all backgrounds, so join us for a comfortable and unforgettable time in our beautiful and historic city. Our space is privately operated by us, not a rental company. We live onsite, and been here for 20 years.

4.89 out of 5 average rating, 391 reviews

Flat in Downtown Dubuque

1129#1/ Market view studio-steps Millwork district

This is one of the best locations to be in downtown Dubuque. Few blocks access to Highway 61, Highway151 and Highway 20. Right on the farmers market (May through October). Five Flag Center, Art museum, Millwork district, Restaurants, Breweries and Coffee house all with in walking distance. You’ll have: - premium pillows - Memory foam queen mattress. - Smart TV. High speed Internet - Keurig Coffee maker - Regular & decaf coffee and tea - One off street parking You’ll absolutely love it here.

4.98 out of 5 average rating, 299 reviews

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.

4.95 out of 5 average rating, 340 reviews

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.

Treehouse in The Galena Territory

4.98 out of 5 average rating, 157 reviews

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

4.98 out of 5 average rating, 362 reviews

Suite Victory #2 On Main St w/Reserved Parking

Suite Victory #2 (facing Main St.) Beautifully renovated apartment on Main St. right where you want to be with Reserved Parking. Dining, entertainment, and shopping just outside your door. Large open floor plan with beautiful views of downtown on the corner of Main Street and the old cobbled Perry Street. King bed. Double sink vanity and large walk-in shower. Kitchen has oversized island, quartz countertops, and new appliances. Full size washer and dryer within unit. MAX 2 PEOPLE

4.92 out of 5 average rating, 344 reviews

Chalet in Elizabeth

Galena Country Getaway

Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

4.96 out of 5 average rating, 541 reviews

Home in Galena

Beautiful Miner's Cottage in a Garden

This 1840's miner's cottage in the heart of Galena is only 3 blocks from beautiful, historic and fun Downtown Galena Main Street, but is far enough to have quiet times in the quarter acre yard of perennial gardens as well the expansive 2 story front porch, and 3rd porch off the kitchen, with gas grill. The house sits on a corner lot in the Galena National Historic District. The bathroom and kitchen are newly remodeled and the entire house is designer decorated. Beautiful!

Cabin in The Galena Territory

4.98 out of 5 average rating, 113 reviews

Family Time! Hot Tub•Fire Pit•Game Room•3 Kings!

Ultimate Family Escape in Galena Territory! Unwind, explore, and make memories at this chic, spacious cabin! Sip coffee on the deck as deer wander by, soak in the hot tub, and gather around the fire pit for s’mores. Stay cozy by the wood fireplace or challenge the family with arcade games, air hockey, pinball, and darts! Enjoy Owner’s Club access with a pool, fitness center & pickleball (8 amenity cards). Adventure awaits—book your perfect getaway today!

Townhouse in The Galena Territory

4.9 out of 5 average rating, 115 reviews

Spring Creek Sanctuary

Come enjoy nature's splendor at the "Spring Creek Sanctuary", a modern condo located in the Galena Territories. Our two spacious bedrooms & two bathrooms allow for groups or families to stay in comfort and style. All can congregate in the shared spaces to enjoy a well stocked kitchen, cozy living room with a wood burning fireplace and the deck area with it's beautiful views. Be sure to check out the amenities included with your stay!

5 out of 5 average rating, 341 reviews

Dawson's Remise Luxury Accommodation

Enjoy a luxurious stay in our remise ("carriage house"), complete with authentic Art Deco and Industrial furniture and design. We took great care in ensuring top notch craftsmanship and amenities, so as to create an inviting environment that you won't want to leave! Hidden away off the quaint and historic Park Avenue, you'll enjoy a quiet and restful stay whilst within walking distance to Main Street Galena and all it has to offer.

Holiday rentals for every style

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Convenient locations with everyday essentials

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Popular amenities for Galena holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Galena

5 out of 5 average rating, 117 reviews

Ulysses Suites, Suite 203

MaryRating, 5 stars1 month ago

A friend and I stayed in this beautifully appointed apartment for 3 nights. This is a very well thought out, finely decorated space. The decor is attractive and high quality. The beds are comfortable, the kitchen is well equipped and there are many nice touches throughout the apartment such as robes, nice dishes and glass ware, toiletries and good security. The place is located centrally to Main Street for dining and shopping and within walking distance to most of the attractions of Galena. There are two main entrances to the hallways leading to the individual apartments. One is from Main Street and the other is from Bench St. I will say that while the Bench St entrance itself is very nice, the building is on a street that has seen better days. I hope the rest of the buildings will follow suit to improve their street appeal because the first impression made us wonder if we had the right address. We expected from the photos that this would be in a better kept area.

5 out of 5 average rating, 119 reviews

Ulysses Suites, Suite 303

AnnaRating, 5 stars3 weeks ago

Suite 303 in Ulysses Suites was the most luxurious and pristine Airbnb I’ve ever stayed in. It was absolute heaven. Beautiful, clean, convenient, and comfortable. Even the common areas outside of the suites were gorgeous and spotless. I love that the lobby has still and sparkling water on tap. This was worth every penny.

5 out of 5 average rating, 13 reviews

Main Street Views Apartment

ShanaRating, 5 stars1 week ago

Our stay in Galena was great. The airbnb was right in the middle of all the shops and restaurants, and the parking spot helped relieve the stress of searching on Main Street.

4.94 out of 5 average rating, 18 reviews

Cabin in Elizabeth

Hot Tub+ Firepit+ "Tiny"house+ Views+ Galena Area

SaraRating, 5 stars1 week ago

Loved the stay at Kettle Noir! Such a gem of a place outside Galena, close enough for shopping, goat yoga, spa and dining but far enough to be quiet and peaceful with so much space for a weekend getaway. Thanks Adnan, can’t wait to come back soon!

4.87 out of 5 average rating, 759 reviews

Loft in Galena

The Brick Apartment Main Street Galena

Matthew PorterRating, 5 stars2 weeks ago

Perfect spot for spending a couple nights in Galena. Right on the main drag and easy to get to everything. Part of the package was free coffee in the cafe right below the space. Jack was the perfect host and highly recommend.

Superhost

Loft in Galena

4.85 out of 5 average rating, 527 reviews

Million Dollar View Main Street Galena

StephanieRating, 5 stars2 weeks ago

Great location - easy to get to. Parking was not a problem for us. Kitchen has everything you might need except we couldn't find coffee filters. There is street noise as reviews said. We brought ear plugs but didn't need them. Cute place - worked well for our needs. Definitely recommend.

4.94 out of 5 average rating, 16 reviews

Private room in Galena

B&B Close to Main St - Suite 2 - No Cleaning Fee

AshleyRating, 5 stars3 weeks ago

I cannot say enough good things about Miss Murphy’s Bed and Breakfast. From the moment I arrived, I felt like I had stepped into a storybook. The house is charming, cozy, and full of character—every detail thoughtfully curated to make you feel right at home. My room was spotless, beautifully decorated, and incredibly comfortable. The location is also perfect—tucked away just enough for peace and quiet, yet still a short stroll from the heart of downtown Galena with all its cute shops and historic charm. If you’re headed to Galena, do yourself a favor and stay here! It’s the kind of place that stays with you long after you leave. Can’t wait to come back!