Holiday rentals in Galena

4.82 out of 5 average rating, 633 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.

Serviced apartment in Downtown Dubuque

4.89 out of 5 average rating, 392 reviews

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.

Villa in The Galena Territory

4.98 out of 5 average rating, 134 reviews

Well-located ~ Outdoor Pool steps away ~ King Bed

✓Near hiking trails & paved walking trails ✓Stonedrift Spa, 3 min drive ✓North Course & Driving Range, 2 min drive ✓Owner's Club access ✓Downtown Galena, 15 min drive ✓Semi-private outdoor pool, steps away ✓Well equipped kitchen w/modern appliances ✓Smart TV on each level w/Roku & YouTube TV ✓Computer desk ✓Fireplace w/supply of firewood ✓Queen sofa bed ✓2 Full baths ✓Gas grill ✓Indoor pool ✓Lake access ✓Chestnut Mountain (Ski & Zipline), 25 min drive ✓Guest favorites: "cleanliness & comfort"

Townhouse in The Galena Territory

4.99 out of 5 average rating, 152 reviews

Are you seeking a stylish and tranquil escape in the countryside? Our fully renovated and modernized townhome is the epitome of luxury and comfort, ensuring a memorable stay. Situated in the picturesque, resort-like Galena Territory, surrounded by lush hills, and with access to a plethora of amenities (e.g., pools, tennis/pickleball courts, gym, game room), our home offers a peaceful retreat while being conveniently close to downtown, golfing, wineries, dining, shopping, and ski (Chestnut).

4.95 out of 5 average rating, 341 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, 159 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, 363 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

5 out of 5 average rating, 117 reviews

Ulysses Suites, Suite 203

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213 to 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 203 is almost 1400 square feet and is located on the 2nd floor.

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, 542 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, 115 reviews

Family Fun! 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!

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Villas

Luxurious estates for the ultimate escape

Flats

Convenient locations with everyday essentials

Popular amenities for Galena holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Galena

Cabin in The Galena Territory

4.98 out of 5 average rating, 62 reviews

5KING Bed 5 Bath~Upscale~Views~Pets~Luxe Amenities

MollyRating, 5 stars3 weeks ago

Excellent experience. This home is magnificent! We had a group of 11 girls, the size, layout and details of this home are truly spectacular. We enjoyed the large balcony, the spacious rooms, and the beds are so comfortable. The kitchen had everything we needed. Each bedroom has its own bathroom- great for 11 girls getting ready. The location is perfect - remote, peaceful but only 15 minutes from downtown Galena. Kapil, our host was great! Very responsive and helpful and kind. Made sure we had everything we needed. They take wonderful care of this home. Great experience overall! Can’t wait to go back!

4.98 out of 5 average rating, 300 reviews

Ulysses Suites, Suite 202

AliciaRating, 5 stars3 weeks ago

Absolutely spotless and lovely! Loved the small touches and couldn’t as for a better location. Never even had to move our car! Even though it was rainy and pre-busy season, we had a great time and are looking forward to our visit later this summer!

4.93 out of 5 average rating, 14 reviews

Farmhouse Style Apartment

LaurenRating, 5 stars1 week ago

Clean, easy to find, Mark and Lisa were helpful and responsive! We loved the "Welcome" cookies they left for us upon checking in!

5 out of 5 average rating, 119 reviews

Ulysses Suites, Suite 303

AnnaRating, 5 stars1 month 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.

4.95 out of 5 average rating, 19 reviews

Cabin in Elizabeth

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

ColleenRating, 5 stars4 days ago

This was a three day girls weekend we had everything we needed and weren’t far from downtown galena the area was quiet and peaceful we all had a great time

4.87 out of 5 average rating, 761 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.

Home in The Galena Territory

5 out of 5 average rating, 37 reviews

Golden Meadows Escape: A Luxurious Country Retreat

SimoneRating, 5 stars2 weeks ago

This place was incredible! We almost thought it was too good to be true but it was completely how it was described. The surrounding area was beautiful and we’re definitely interested in coming back now.