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Vacation rentals in Lena

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Top-rated vacation rentals in Lena

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

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Top guest favorite
A cozy cabin is nestled on a grassy hillside, surrounded by trees. A wooden deck wraps around the cabin, providing outdoor space. Stone steps, lined with potted flowers, lead up to the cabin entrance, enhancing the natural setting.
Cabin in Benton
4.95 out of 5 average rating, 127 reviews

Our cabin's a win-win

In 1834, it was a chicken coop nestled between the house and barn. Today, it's a cozy cabin just a stone's throw away from the villa and venue. From the private, rural setting to the rustic decor, you'll feel as though you've traveled back to simpler times. It's unique, refreshing and oh-so tranquil. If you're looking for a little hush and a lot less rush, you're going to fall in love with this little home away from home. While you're visiting, get the scoop on how we transformed this coop.

Top guest favorite
The living room features a gas fireplace set into a neutral wall, complemented by two armchairs and a green couch. Natural light streams through large windows, showcasing a reading nook with a bench. Shelves display decorative items and a smart TV is mounted above the fireplace.
Loft in Monroe
4.98 out of 5 average rating, 198 reviews

Loft 3 - On The Historic Monroe Square

Loft 3 is 40 steps (2 flights of stairs) above the Monroe Square. It's a climb, but the view is totally worth it! Newly remodeled in 2021, and reminiscent of the 1859 character of the building, this space is cute, cozy, and truly one of a kind. Literally a couple steps away from your entryway is Sunrise Donut Cafe, featuring customized donuts and a full menu of excellent coffee items. From there, explore the rest of the Square for food, drinks, and shopping in a quaint Main Street atmosphere.

Top guest favorite
An open living area is featured, showcasing a cozy sofa adorned with decorative pillows. A patterned chair with the word 'home' is positioned next to a small wooden table, which holds a few items. The area is brightened by natural light from sliding glass doors.
Home in The Galena Territory
4.98 out of 5 average rating, 151 reviews

Wooded Villa • Cozy King Bd • Pool • Near Spa, Ski

Escape to this peaceful golf villa tucked among whispering woods with a seasonal view of Hole #11 on the North Course. Just 12 minutes from downtown Galena, it’s a perfect cozy retreat for two—where relaxation meets adventure. It offers a cozy king bed for dreamy nights and an inviting retreat made for quiet moments together. Stroll to the nearby pool, spa, or trails, then unwind by the fire after a day of golf or winter fun. Includes full access to the Owner’s Club with an indoor pool.

Top guest favorite
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
4.96 out of 5 average rating, 328 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.

Top guest favorite
The exterior of a single-family home is showcased, featuring a two-car garage with turquoise doors. Lush green grass surrounds the driveway, and colorful flowering plants are positioned near the entryway. A clear blue sky serves as the backdrop.
Guest suite in Freeport
5 out of 5 average rating, 106 reviews

Lower Level Suite in Home-Private Entrance!

⭐️ Large lower level walk out apartment for up to 7 people, ⭐️separate entrance in single family home in a quiet upscale neighborhood. 💡Lighted sidewalk. ⭐️Gas in wall heater supplements heating needs in winter. Sleeps up to 7 guest with 🛌1 king bed (heated mattress pad) in master, common area has 🛌 4 Twin XL beds w/memory foam mattresses and 🛌 1 additional Twin XL bed in bonus room. ⭐️ Free Washer/Dryer in apt. w/3 courtesy soap pods. 👶🏻 Pack n Play 🍼 high chair.

Top guest favorite
An open living area features a comfortable gray sectional sofa and a coffee table. A dining table for four is visible, accompanied by white chairs. Natural light fills the space through a window, while green plants and modern decor add a touch of freshness.
Guesthouse in New Glarus
4.98 out of 5 average rating, 270 reviews

Fresh & Bright Apartment Getaway in New Glarus

We would like to welcome you to our bright newly built 2nd floor above garage apartment. Located in a family friendly neighborhood, just a 10 minute walk to downtown where you will find delicious dining, unique shops and historical sites everywhere you turn. Jarod and I with our kids live in the main house. We love giving our guest privacy but may run into you as we are enjoying the weather as often as we can with our kids running around enjoying their childhood.

Top guest favorite
The image showcases a charming, two-story building with blue patterned brickwork. A welcoming storefront features a striped awning and decorative planters. Natural light brightens the entrance, and a tree partially frames the scene, contributing to a lively, urban atmosphere.
Apartment in Monroe
5 out of 5 average rating, 262 reviews

MJ's Penthouse ( A piece of paradise in Monroe)

A beautiful 2000 square foot second floor Penthouse that offers an excellent view of the historic court house and square. Our location gives you walking distance to all places on the square including the 2nd oldest brewery in the country, boutiques, hair and nail salons, home decor , antique shops, clothing and apparel, specialty treats, restaurants and bars. We have free parking out front on the square and also a private elevator for our guests special needs.

Guest favorite
A spacious outdoor deck is featured, surrounded by lush greenery. Several chairs and a table are positioned for seating, with large windows of the cabin visible in the background, allowing natural light to illuminate the interior.
Tiny home in Thomson
4.87 out of 5 average rating, 469 reviews

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.

Top guest favorite
The farmhouse is shown from the exterior, showcasing a two-story structure with white siding and a covered front porch. Flower planters hang from the porch railing, and a stone pathway leads to the entrance. Green grass surrounds the house, bordered by a paved area.
Home in Gratiot
4.99 out of 5 average rating, 253 reviews

The Old Farmhouse

The old farmhouse is located on a quiet, dead-end road. It sits on top of a picturesque hill surrounded by rolling farmland. The Pecatonica river surrounds the farm on three sides. The farmhouse is the perfect place for quiet time and relaxation. The Farmhouse was built in 1914. It still has the original woodwork, and beautiful hardwood floors. Sit on the porch or sit around the fire pit and enjoy the beautiful fall foliage.

Top guest favorite
The rustic retreat features a charming exterior with a red wood-paneled facade and a green metal roof. A welcoming porch is adorned with outdoor seating and surrounded by vibrant greenery, including flowering bushes and hostas, creating a serene entrance.
Barn in Freeport
4.97 out of 5 average rating, 575 reviews

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 and possible kayaks. 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.

Top guest favorite
The exterior of a revitalized 1950s car wash is showcased, featuring a curved awning and a large glass door. The building has a bright white facade with a red accent roof, and signage reading 'The Car Wash Inn' and '$1.25 WASH' is displayed.
Home in Shullsburg
4.99 out of 5 average rating, 195 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

Guest favorite
A cozy living room is featured with large windows allowing natural light to fill the space. Two comfortable chairs are positioned beside a small table, while a soft rug lies on the hardwood floor. A gray sofa and a floral artwork complete the welcoming environment.
Apartment in New Glarus
4.96 out of 5 average rating, 180 reviews

Cozy Upper Flat in New Glarus

Welcome to my upper flat (private staircase to 2nd story) one block from Downtown New Glarus where you will find charming shops, tasty eats & activities! This unit can accommodate 4 people. There is a king sized bed & queen pull-out couch. Kitchen is fully stocked with a refrigerator, range/oven, toaster & coffee maker. Complete with cozy eat-in area! Living room has wall of windows & smart TV. W/D are included.

Popular amenities for Lena vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Stephenson County
  5. Lena