Holiday houses in Jo Daviess County

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!

Superhost

Home in Bellevue

4.79 out of 5 average rating, 99 reviews

Mississippi River house has everything you need

Your family will be close to everything when you stay at this centrally-located place. The river is right across the street and so is the walkway the walkway will take you all the way to the other end of town beautiful walk along the river. Richmond‘s café Great place for breakfast. The brewery has igloos to sit in outside just two blocks from the guest house. The river park will be lighted for Christmas right across the street all the way through the end of town Great place to be this holiday

4.98 out of 5 average rating, 134 reviews

Villa in Galena

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"

4.98 out of 5 average rating, 159 reviews

Treehouse in Galena

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

4.95 out of 5 average rating, 181 reviews

Tiny home in Dubuque

Off-grid Tiny House farm stay

The perfect place for 1-2 guests to unplug and relax in this beautiful, natural setting. It's a short distance (less than 2 min. walk) from the parking area to this quiet, private, 12'x14' one-room cedar cabin set on a pasture with picture-window view of wooded bluffs and stream, birds and other wildlife. Writing table and chair, glider rocker, woodstove, and gas cookstove. Solar-powered desk lamp. Port-a-potty and solar shower outside (summer only). Fire pit and outdoor seating.

4.95 out of 5 average rating, 242 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.

5 out of 5 average rating, 117 reviews

Apartment in Galena

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

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!

4.98 out of 5 average rating, 115 reviews

Cabin in Galena

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!

5 out of 5 average rating, 343 reviews

Apartment in Galena

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.

4.96 out of 5 average rating, 142 reviews

Townhouse in Galena

Contemporary Country Villa with Golf Course View

COMPLETELY UPDATED!!! 1 BR/ 2BA golf villa on the 10th hole. Upstairs in the unit features the bedroom with a queen-sized bed with memory foam mattress, and an adjacent full bath, and washer/dryer. Downstairs is the living room with wood-burning fireplace, slider to deck overlooking the 150-yard marker, kitchen and another full bath. Smart TVs for you to log into your streaming services (AmazonPrime, no cable.)

Holiday rentals for every style

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Convenient locations with everyday essentials

Popular amenities for Jo Daviess County holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Jo Daviess County

4.93 out of 5 average rating, 14 reviews

Apartment in Galena

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!

4.98 out of 5 average rating, 81 reviews

Cozy Galena Townhome

AlexRating, 5 stars3 weeks ago

Chelsey’s condo is the perfect city escape due to its idyllic location in a wooded setting that makes it an oasis for any traveler. The unit itself is well appointed with comfortable beds and is incredibly clean. Don’t look any further if you’re planning a visit to nearby Galena!

4.89 out of 5 average rating, 63 reviews

Apartment in Elizabeth

Derinda house B&B private apartment.

TiffanyRating, 5 stars1 month ago

This was my fourth time staying at Sandys and each time is just as enjoyable as the last. Her new wallpaper in the kitchen, bedrooms, and master bath are beautiful. She has a real knack for decor. She's always super helpful, kind, and her breakfasts dont disappoint! If you're looking to relax in a peaceful setting, but still be close to downtown Galena, this is THE place to stay.

4.98 out of 5 average rating, 65 reviews

Cabin in Galena

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

DianaRating, 5 stars1 week ago

I enjoyed this place we stayed. It was close to Galena just like we thought. It was comfortable. The place was very clean. The hot tub was relaxing. The only thing I missed was a coffee pot. However, there were coffee pods for our use. As well as s’mores and hot coco for the kids. That was a nice touch! I would definitely stay here again!

4.98 out of 5 average rating, 41 reviews

Cabin in Elizabeth

The Little Dipper A-Frame in Galena Country

LindsayRating, 5 stars5 days ago

We enjoyed exploring Elizabeth and Galena by day, and relaxing on the deck with a peaceful view each evening. Perfect anniversary weekend. The house is cozy and welcoming.

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

4.94 out of 5 average rating, 65 reviews

Galena Getaway Retreat | 3BD/3BA | Hot Tub + Games

StaceyRating, 5 stars2 weeks ago

The Ravine Lodge is a relaxing spot to truly getaway and unplug. A short distance to downtown Galena and a few miles to the main Owners Lodge where the pool and gym are located. Windy roads so driving at night may not be ideal for some. Home was very clean and had all the amenities. We would come back!!