Holiday rentals in Elizabeth

4.99 out of 5 average rating, 152 reviews

Townhouse in Galena

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).

4.98 out of 5 average rating, 301 reviews

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.

4.98 out of 5 average rating, 757 reviews

Tiny home in Darlington

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

4.98 out of 5 average rating, 161 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

4.96 out of 5 average rating, 302 reviews

Cabin in Savanna

Cozy, Secluded Cabin -A Peaceful Getaway Location!

Located just a half mile from town, but secluded enough to be a private hilltop house retreat. The deck overlooks downtown with a backdrop of the Mississippi River! Enjoy the outdoors hiking at the Palisades State Park with miles of trails just a short drive away, kayak or fish one of the many rivers or lakes, stroll through downtown for antique and gift shopping, or visit a nearby winery. After a day of adventures, relax in the spa tub or enjoy a glass of wine on the private deck.

4.95 out of 5 average rating, 244 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.

4.92 out of 5 average rating, 347 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, 544 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, 117 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!

4.82 out of 5 average rating, 792 reviews

Loft in Galena

Rustic Apartment Main Street Galena

Hey there! We exposed the old original brick and hard wood floors inside. We installed an electric fireplace with a big comfy couch right in front of it. We do have cable TV with a variety of channels for you. There is a kitchen complete with an oven, stove, microwave and fridge if you are going to channel your inner chef. The bathroom has a shower and tub, and a built-in bathroom heater to keep it warm for you! This apt is above a coffee shop!

4.87 out of 5 average rating, 437 reviews

Tiny home in Thomson

Cozy Cabin on the Mississippi River

This cabin is located on the serene backwaters of the Mississippi. It is the perfect destination for a weekend getaway, or ideal spot to rent for fishing tournament‘s or duck hunting. This cabin is situated next to pool 13, and there is plenty of space for multiple vehicles and boats to park. Only half a mile away from the loading dock and close by to an Illinois State Park, our cabin allows Guests to enjoy nature in a relaxed setting.

5 out of 5 average rating, 163 reviews

Home in Shullsburg

The Car Wash Inn A Unique Stay

Enjoy a unique stay inside a beautifully revitalized single bay 1950s car wash. Only minutes away from historic downtown Shullsburg. This space has been thoughtfully designed to retain it's industrial charm with a nostalgic ambiance, while offering modern amenities for a comfortable stay. ~20 miles to Galena, IL ~25 miles to Mineral Point, WI ~25 miles to Dubuque, IA ~ATV Trail Access with large parking area

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Pool

Free parking on premises

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Other great holiday rentals in Elizabeth

4.91 out of 5 average rating, 11 reviews

Cabin in Elizabeth

Secret Haven Log Cabin

SharonRating, 5 stars8 months ago

John's cabin was great for our group. It was easy to find and so quiet and peaceful. The beds were so comfortable and everyone enjoyed our stay.

4.98 out of 5 average rating, 85 reviews

Cozy Galena Townhome

KathleenRating, 5 stars3 days ago

The condo was immaculate and comfortable. Check in was easy and the host provided helpful information about finding the local store as well as a route suggestion to avoid exiting the neighborhood on a blind curve. Would definitely stay here again.

4.89 out of 5 average rating, 63 reviews

Flat 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.

5 out of 5 average rating, 7 reviews

Home in Elizabeth

Hell's Branch Cabin

GRating, 5 stars5 months ago

We had a great time at this location. Our host, Margaret was extremely helpful and welcoming. The house and the property were beautiful and what we were looking for. We had plenty of space for our family to celebrate the holidays. Margaret was very responsive and kind when we had any questions. She even brought a family member's lost coat to the house when a business called her about it. She went above and beyond. I definitely recommend this property and the host.

5 out of 5 average rating, 3 reviews

The Tree House

BriannaRating, 5 stars1 week ago

Katherine's Airbnb was the perfect spot to unwind and be with nature. The space is about 15 minutes from downtown Galena, the drive is doable, but you really feel like you are in the middle of nowhere! It is situated in a wooded area, located up in the hills, surrounded by beautiful trees, wildlife, and farmland. Minimal sound or light pollution - truly peaceful! The space itself looked identical to the pictures listed. The design choices were perfect. Giving the space a cozy, clean, and updated feel while encasing some of its original charm. The only heads up I will give folks is that there is only a stove, not an oven, to cook with, but there is a microwave. Aside from that, the kitchen had all the other tools needed to cook! I would definitely come back here!

4.95 out of 5 average rating, 20 reviews

Farm stay in Stockton

“The Farmhouse” a ranch style country guesthouse

JessicaRating, 5 stars4 weeks ago

We took a very last-minute trip from Chicago over Memorial Day weekend and ended up having the best time! We truly enjoyed the peace and quiet of the countryside, and our kids absolutely loved interacting with all the animals. Just as promised, their sweet dog Teddy greeted us upon arrival, and their goat Goose made a fun morning appearance. Joan and Jean were both incredibly friendly and accommodating throughout our stay. We had a small issue the first night (completely out of their control), but they responded promptly and went out of their way to ensure it was resolved quickly. The location is great—peaceful and relaxing, yet close enough to explore nearby spots like Galena and even Dubuque, IA, which is just under an hour away. It was exactly the kind of getaway we needed to unplug from the hustle and bustle of city and work life. Thank you again for everything—we hope to be back soon!

4.95 out of 5 average rating, 22 reviews

Cabin in Elizabeth

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

JacquelineRating, 5 stars6 days ago

I had a fantastic stay! The accommodations were super comfortable, and the space was decorated so cutely—it had such a welcoming and cozy vibe. Everything I needed for a relaxing weekend was thoughtfully provided. The host was incredibly responsive and made everything so easy with clear instructions for the home, plus helpful recommendations for things to do around town. It really made the whole experience seamless and enjoyable. I would definitely stay here again!