Holiday rentals in Lena

Doe Meadow, a tiny house farm stay

Doe Meadow is my newest custom designed tiny house nestled along the drive to my family farm. Sharing my little slice of heaven with guests is something I have found great joy in. Rural tourism is my passion, & all the farm animals are anxiously awaiting your visit- treats in tow- of course! I wanted to create something unique, a place to make memories, & somewhere you'll want to come back to. Settle in the hammock, listen to the peaceful wind chimes, watch the goats & mini cows graze, unwind.

Hudson Hotel

Located in picturesque Stockton, Illinois, this 4-bedroom home boasts numerous updated features including a new kitchen and bathrooms. Ideal for family getaways, group trips, or business stays. Situated conveniently within walking distance of essential amenities such as a grocery store, gas station, local restaurants, bars, and a town pool, it ensures convenience and accessibility. Nearby attractions include the charming towns of Galena, Dubuque, and Freeport, enhancing the appeal of your stay.

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

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Rustic Barn Loft at Oak Springs Farm

Unplug in our gorgeous barn loft above our working barn. Sleep to the sound of crickets and frogs in the pond, then wake up and pet the sheep, goats, rabbits, cats, ducks & chickens. Open floor plan, cathedral ceiling, farm decor, fire pole, sliding barn doors. Full kitchen, jetted tub, rain shower, laundry. Stone patio, fire pit. 2 bedrooms, sleeper sofa, air mattresses. Juice, coffee, and fresh eggs provided when the hens are laying. NO A/C. ABSOLUTELY NO PETS Facebook oakspringsfarmwi

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

Walk everywhere in downtown Freeport.

Downtown Freeport, walking distance to movies, bars, restaurants. Some of the summer activities include concert on the square once a month, market every Saturday. The largest car show with 1000 old cars, the air show. If you like to walk or ride a bike there’s Jane Adam’s trail. Krape park is beautiful with many trails on the river where you can rent kayaks. The kitchen is apartment sized but boasts a counter top induction cook top, oven, microwave, Keurig,and refrigerator.

Deer Trail Cabin

🌿 Cozy cabin tucked in the quiet Wisconsin woods—your perfect spring retreat. Enjoy fresh air, blooming trees, and peaceful forest trails right outside your door. Relax in the outdoor hot tub under the stars, gather around the fire pit in the evening (bring your own wood or collect from the property), and watch the free-range goats and chickens roaming the property. A peaceful, private getaway for couples, small families, or anyone looking to unwind in nature. 🌿

Historic Square Loft | Walk to Restaurants & Shops

Stay on Monroe’s Historic Square—park once and walk everywhere. This bright, quiet downtown loft is steps from coffee, restaurants, shops, brewery tours, and local events. Ideal for couples, professionals, and weekend getaways, with easy self-check-in, reliable Wi-Fi, a dedicated workspace, and a full kitchen. Perfect for Cheese Days, courthouse visits, and downtown weekends. Quiet hours ensure a peaceful night’s sleep.

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

Cute Little Country Guest House

An old barn/machine shed transformed into a great little rustic retreat (which we affectionately call "Westhaven")! A great secluded place to get away from the day-to-day grind. Hiking trails on the premises. About 5 miles from civilization (town). Come unwind! FRIENDLY DOGS WELCOME (we speak fluent WOOF! :-) ) (Please NO cats!) This is not just a place to stay, but an experience to remember.

Howardsville Schoolhouse

This lovingly restored schoolhouse blends history with modern comfort. Set in a peaceful rural location, it features an open living area, fully equipped kitchen with seating for 12, and cozy sitting area with fireplace and play area. Enjoy a spa-like bath with clawfoot tub, king bedroom, and laundry. A perfect mix of new, refurbished, and antique details create a unique, inviting retreat.

Peaceful Cabin Escape • Stargazing & Nature

🌲 Peaceful country cabin retreat 🌲 Soaking tub for ultimate relaxation 🛁 🌲 Cozy loft with twin beds 🌲 Recreation room with bar & lounge 🍻 🌲 Quiet rural setting perfect for stargazing ✨ 🌲 Queen bedroom on main level 🌲 Fully equipped kitchen 🍽️ 🌲 Grill for outdoor dining 🌲 Fast WiFi & keyless entry 🌲 The perfect place to unplug and unwind