Holiday rentals in Lena

The Bower-Cozy Tiny home w/friendly farm animals

Escape to The Bower at Arbor Crest Acres, a peaceful woodland retreat designed with care and comfort in mind. Enjoy restful nights and unwind in a cozy, thoughtfully crafted space-perfect for slowing down and appreciating the serene beauty of Southwest Wisconsin’s countryside. As you explore, you will be greeted by our friendly animals: gentle Great Pyrenees on patrol, playful barn kitties, free-range chickens, adorable goat mamas and their babies, and shy ducks that seek refuge among the pines.

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.

D&D Coastal Farmhouse Apartment Not near any water

This building was built in the late 1890's and was the main grocery store in South Wayne, WI. For years it was used as storage until Dan and Deb renovated it over the last year into this beautiful space! Plenty of parking and great food options within 1 block make D&D Coastal Farmhouse Airbnb a great choice for your stay in Southwest Wisconsin. Main Hubs within 45 minutes: Dubuque, Madison, New Glarus, and Rockford Not handicap accessible. Must Be able to climb stairs. Off street parking.

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.

The Hideaway

Unwind in this calm, stylish hideaway! You’ll be close to Monroe and Cadiz Springs State Park. Within walking distance of The Vault Bar & Grill and near Hawk’s Mill Winery, enjoy a fully stocked kitchen, Wi-Fi, street or garage parking, easy access to the Cheese Country Trail just across the road, and plenty of room for your ATVs, UTVs, or snowmobiles. The space features 1 bedroom with an adjustable bed, plus an air mattress if needed. Enjoy a cozy, comfortable stay with everything you need.

Willow Lake Getaway Cozy for 2 - or large families

Beautiful 4 bedroom private lakefront home, cozy enough for 2, large enough for family gatherings for holiday/wk end escape/vacations. Hot tub for cool eves October-April. Extensive private decks with BBQ, outdoor dining & circular daybed with umbrella. 2 docks, 2 SUP boards, paddle boat, 2 kayaks, pingpong table, books and board games. 2 Master Suites with smart tv with private balcony & seating area. fire pit located next to 1st dock. Couples get a 10% discount, message me for details.

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

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.

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

Farm Stay | ATV Trails | Large Yard | Near Galena

Escape to this cozy 4-bedroom, 1-bath farmhouse on the Wisconsin–Illinois state line—perfect for relaxing, reconnecting, and enjoying a peaceful countryside getaway. ✨ HIGHLIGHTS • Located on ATV/UTV + near snowmobile trails 🏍️ • Spacious yard + country views • Classic farmhouse charm + natural light • Large dining space for groups • Smart TVs in every bedroom • 12pm check-in & check-out • ~30 minutes to downtown Galena • Ample parking for trailers + gear

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.