Holiday rentals in Massbach

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Top-rated holiday rentals in Massbach

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Top guest favourite
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.

Guest favourite
A vibrant living area features a blue sofa and a colorful accent rug adorned with floral patterns. Multiple seating options, including stools in red, green, and blue, surround a coffee table. Natural light streams through two large windows, brightening the space.
Apartment in Hanover
4.96 out of 5 average rating, 74 reviews

Where Time Stands Still ~ Near Galena

Cozy vacation stay on the water in beautiful Jo Daviess County a wonderful getaway destination. Just 15 minutes from Chestnut Mountain Ski Resort and a scenic 20 minute drive to Historic Galena, Illinois. Exceptional fishing not thirty yards outside your front door. From hiking the Mississippi Palisades State park, biking on the Great River Trail, or teeing off at one of many golf courses the Hanover area has no shortage of outdoor adventures right around the corner. We hope to see you soon.

Top guest favourite
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.

Guest favourite
An outdoor seating area is presented with a round table surrounded by six wrought iron chairs. A potted plant adds a touch of color to the table, while flowers are visible in the flower beds nearby. Large windows on the house allow natural light to enter.
Townhouse in Bellevue
4.92 out of 5 average rating, 224 reviews

Pet friendly, 2 BR close to Mississippi River

This comfortable home is a 2 BR 1 BA with a full kitchen, and off street parking. It is 1 block away from the Mississippi River and within walking distance to local shops, restaurants bars, parks, and walking trails. The local grocery store is located directly across the street. Well behaved pets are welcome. The backyard is completely fenced in. NO SMOKING INSIDE. As stated in the other notes section, we are located along the Canadian Pacific Railroad and there will be trains going by.

Top guest favourite
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 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
4.96 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 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
4.92 out of 5 average rating, 361 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

Superhost
A charming kitchen corner features a two-tone hutch displaying white dishware on open shelves. A small potted plant sits on the table beneath the hutch, which is complemented by decorative items and artwork on the walls, enhancing the cozy dining atmosphere.
Cottage in Savanna
4.9 out of 5 average rating, 220 reviews

Cozy Cottage getaway close to River, Casino,antiq

Owners are next door. River and marina short block away within walking distance. Grocery store half a block away within walking distance. Downtown less than a mile. Galena about half hour. Iowa 5 min away and casino in Iowa 20-25 min. Palisades State Park 5 min away. This is a cozy cottage with use of deck and grill, and full amenities to cook in house if you like. Check out C-Savanna for other great, adventurous, and scenic things to do while visiting. Great Getaway

Guest favourite
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 favourite
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 favourite
A spacious kitchen features a large island with four stools and sleek cabinetry. Modern stainless steel appliances are showcased, along with a stylish tile backsplash. Natural light streams in through a window, highlighting the open design that connects to the adjoining living area.
Home in Galena
4.96 out of 5 average rating, 107 reviews

Hot Tub + Fall Views | Peaceful Escape

Welcome to Pine Ridge—a peaceful, modern 2-bedroom, 2.5-bath vacation rental in The Galena Territory. With two king suites, a cozy living area, forest views, and a private hot tub, it’s perfect for couples, friends, or a remote work getaway. Relax on the porch, unwind by the fireplace, or explore nearby trails, shops, and GTA amenities. Just 5 minutes to the Owners Club and 10 minutes to downtown Galena.

Guest favourite
A bright living area features a teal couch paired with a wooden coffee table. Natural light enters through a window dressed with light gray curtains. The staircase is visible in the background, leading to additional areas of the apartment.
Flat in Downtown Dubuque
4.92 out of 5 average rating, 349 reviews

1129#2 / Farmers Market Gem: Steps from Ballroom

Charming 1BR loft in the heart of Dubuque’s Millwork District—perfect for solo travelers or couples. Bedroom is in an open loft (stairs access); bathroom on main floor. Across from seasonal farmers market (May–Oct), steps to restaurants and riverfront. Features a full kitchen, cozy living area, historic touches, and easy self check-in. Affordable, clean, and walkable to downtown highlights!

Popular amenities for Massbach holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Jo Daviess County
  5. Massbach