Holiday houses in Lena

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Top-rated holiday rentals in Lena

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of a two-story house features a peaked roof, white wood siding, and a covered front porch. A dark front door is flanked by two windows. A pathway leads up to the porch, accompanied by a potted plant and lush greenery.
Home in Stockton
4.92 out of 5 average rating, 39 reviews

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.

Top Guest favourite
A well-lit bedroom features two spacious beds with light bedding. Each bed is complemented by a decorative throw at the foot and is flanked by nightstands. Simple wall decor and plants enhance the decor, while a ceiling fan provides comfort.
Apartment in South Wayne
5 out of 5 average rating, 24 reviews

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.

Top Guest favourite
Home in South Wayne
5 out of 5 average rating, 39 reviews

Buck Moon, ATV trail and goats!

Buck Moon is my newly renovated retreat. Designed as a family retreat, nestled into our family farm, I wanted to share this special place with guests. A perfect place to unwind and get away from the city! Catch the sunrise or the sunset from the hammock, take in the starry night sky from the cozy patio, or get a great dose of laughter from playing with my goat kids! Located on an ATV trail road, you have quick access to all the fun adventures of touring the rolling hills of Lafayette County!

Top Guest favourite
Cabin in Elizabeth
4.98 out of 5 average rating, 132 reviews

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.

Top Guest favourite
A wooden swing hangs from a tree in a lush green field, gently swaying in the breeze. In the background, the log home is set atop a hill, showcasing its wrap-around deck and panoramic views of the surrounding landscape under a clear blue sky.
Guesthouse in Stockton
4.99 out of 5 average rating, 406 reviews

HighviewCountry Escape-log home-family farm w/view

Whether you want a staycation or just a weekend away, we have the place for you! Quiet secluded setting, with spectacular view, on one of the highest hilltops in Illinois! Morning sunrises are exceptional. Evening sunsets are breathtaking. Starry nights are amazing. Something in every season! Not far from Galena and other small towns that offer charm, restaurants and shopping. Our rental is fully independent and has everything that you need for your getaway. Please see all photos.

Guest favourite
A cozy living space features a navy blue sectional sofa adorned with a colorful throw pillow. A round coffee table displays brightly colored books. Light fixtures are mounted on the wall, and a dark area rug contrasts with the wooden floor. Hallways lead to other areas.
Home in South Wayne
4.97 out of 5 average rating, 33 reviews

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.

Top Guest favourite
Home in Freeport
4.99 out of 5 average rating, 206 reviews

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.

Top Guest favourite
A friendly sheep stands in a green pasture, its fluffy wool coat visibly soft and light-colored. The sheep's gentle expression is captured as it gazes directly at the viewer, with trees and a cloudy sky in the background.
Farm stay in Argyle
4.98 out of 5 average rating, 335 reviews

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

Top Guest favourite
A charming exterior view of the house is shown, featuring a welcoming porch with wooden seating. The deck extends from the entrance, surrounded by greenery and trees, providing a connection to nature and a peaceful retreat.
Cabin in Savanna
4.97 out of 5 average rating, 396 reviews

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.

Superhost
Home in Apple Canyon Lake
5 out of 5 average rating, 4 reviews

Pool Table + Ping Pong | Fireplaces | Hot Tub

Escape to this spacious 4-bedroom, 5-bath luxury retreat in the Apple Canyon Lake community—perfect for relaxing, reconnecting, and enjoying time together with beautiful lake views and incredible gathering spaces throughout the home. ✨ HIGHLIGHTS • Stunning wraparound stone fireplace 🔥 • Basement game room with pool table, ping pong, foosball + darts 🎯 • Huge wall of windows + soaring ceilings • Large Smart TVs + fast WiFi • Minutes to golf + dining ⛳ • 12pm check-in & check-out

Top Guest favourite
A blue A-frame house is showcased, surrounded by greenery. The brick walkway leads to a cedar deck, framed by landscaping. Windows are visible on the sides, allowing natural light to fill the interior.
Chalet in Elizabeth
4.93 out of 5 average rating, 390 reviews

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

Top Guest favourite
The exterior of the revitalized car wash features a striking white facade with bold red accents. A vintage black truck is parked on the grass, while two bright red chairs sit invitingly near the entrance, adorned with a retro-style sign pointing towards the inn.
Home in Shullsburg
4.99 out of 5 average rating, 228 reviews

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

Popular amenities for Lena holiday rentals