Apartment holiday rentals in Green County

A view from the deck captures the sun beginning to rise over green hills, with warm light illuminating nearby buildings. The scene includes a mix of residential structures, trees, and a glimpse of the surrounding area, creating a peaceful atmosphere.

4.95 out of 5 average rating, 208 reviews

Big Space in the Heart of Little Switzerland

Large, 3-bedroom apartment above a downtown retail store that offers plenty of space to stretch out and restaurants and shops just outside. A public swimming pool, parks, playground, and bike trail are just a short walk away. The space offers an open and well-equipped kitchen for cooking and enjoying a meal with friends and family as well as plenty of comfortable seating for you to curl up, relax, and enjoy a movie. Off-street parking is available so you can avoid the hassle of a busy street.

Guest favourite

The exterior of a cottage-style residence is shown, featuring a sloped roof with red accents. Black shutters frame a large window, while a covered porch provides seating. Lush greenery is present in a planter, and a charcoal grill is visible nearby.

4.94 out of 5 average rating, 51 reviews

McG Resorts Chic Chalet

Enjoy a stylish experience at this centrally-located place. This historic bike/gun shop turned chic chalet-styled cottage is literally steps from a brewery/distillery, stellar restaurants, unique shops & Monroe's historic Square. This cute residence has everything you need whether traveling alone, as a couple, with your friends or family. Professionally designed, this property features all those little extra details to make your stay memorable & shares in the richness of our community's history.

4.94 out of 5 average rating, 81 reviews

On Monroe’s Historic Square-2 bedroom das Baumhaus

DAS BAUMHAUS 2 bedroom, located in the oldest existing building on Monroe’s Historic Downtown Square.A perfect spot to relax and create lasting memories.The picturesque Green County Courthouse,in the heart of the city square, is surrounded by charming boutiques,specialty shops,restaurants and bars.Take a short walk to the Bullquarian Brew Pub on your way to tour the Minhas Brewery,(2nd oldest in the USA) Distillery and Winery.Eat cheese,dine, shop,and enjoy all the amenities Monroe has to offer.

4.99 out of 5 average rating, 78 reviews

Charming Downtown Two Bedroom w/ Fireplace

Prime downtown location in the heart of New Glarus. Easily walk to all the local shops, restaurants, and festivals, offering ultimate convenience and immersion in the town's atmosphere. The apartment's warm decor and inviting fireplace provide a comfortable and memorable retreat that complements the character of the town. Fully-equipped with reserved parking and in-unit laundry. Includes all the conveniences of home, ensuring a stress-free stay for both short getaways and longer visits.

5.0 out of 5 average rating, 461 reviews

The Hideout In Downtown New Glarus

Modern 1 bedroom with a spacious outdoor deck on the second floor of the historic Citizen's Bank building built in 1910. Located above a retail space in the heart of downtown New Glarus. You'll be steps away from restaurants, pubs, shops, park, a bike path, and festivals. This newly remodeled apartment has beautiful quartz countertop & island, and original wood floors. Newly installed large windows allow for ample natural light. Check out The Hideaway if you need a 2 bedroom rental.

Guest favourite

5.0 out of 5 average rating, 22 reviews

The Fishbowl

Welcome to this cozy one bedroom, one- bath retreat just steps from downtown Monroe and the historical square. Perfect for couples, small families, or business travelers, this space blends comfort, style, and convenience. The living room includes a spacious sectional sofa, providing extra sleeping space for children or additional guest while still offering plenty room to relax. The main bedroom is complete with a king size bed, fireplace, large screen TV, and a dedicated workspace.

Guest favourite

A two-story chalet-style building is surrounded by lush greenery. Flower boxes adorn the windows on the upper level, while a sign is visible in the front yard, welcoming guests. The exterior features a combination of dark wood and white siding, set against a clear blue sky.

4.9 out of 5 average rating, 172 reviews

Nördlich Chalet - Trail-side, 1 Bdrm in New Glarus

Enjoy access to all that America's Little Switzerland has to offer! This one bdrm chalet apartment offers a bright spacious living area w/ kitchenette, bedroom and bath, and balcony. Set just off of the highway and next to the biking and snowmobile trails and within walking distance to downtown New Glarus shopping, bars, restaurants, festivals and more, this is the spot to be! Check out Bailey's Run Winery or the New Glarus Brewery and New Glarus Woods State Park, just up the trail!

A modern kitchen is featured with a breakfast bar, equipped with four wooden stools. Stainless steel appliances, including a gas stove and refrigerator, are prominently displayed. Natural light streams in from large windows, creating an inviting and functional space.

4.99 out of 5 average rating, 245 reviews

The Hideaway- Downtown New Glarus

Two Bedroom Apartment in Historic Bank Building This second-floor apartment blends historic charm with modern amenities. Located above a retail shop and steps away from stores and restaurants, it features original wood floors and large windows that fill the space with natural light. The fully equipped kitchen includes a gas stove, pots, pans, and utensils—just bring your ingredients! An in-unit washer and dryer add convenience, making this the perfect home away from home.

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.

5.0 out of 5 average rating, 302 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.

An open living area features a dining table with four chairs, a sectional sofa, and a fully equipped kitchen with wooden cabinetry. Two ceiling fans provide ventilation, while large windows allow natural light to fill the space, highlighting the warm wooden flooring.

5.0 out of 5 average rating, 84 reviews

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.

Two gray armchairs are positioned beside a wooden side table, enhancing the cozy living area. Large windows offer a view of the outdoors, with a mounted deer head adding a rustic touch. A soft area rug beneath the chairs contributes to the inviting ambiance.

4.99 out of 5 average rating, 89 reviews

Fully equipped 2BR*Hidden gem nestled in the woods

Nestled on 4.5 acres of wooded land, this 1200 sqft apartment is yours to enjoy. Large windows look out to the back yard where you may see a deer or wild turkey passing through. Sit on the large porch listening to the birds sing while enjoying a cup of coffee or a complimentary craft beer that can't be purchase in any other state.."Only in Wisconsin". If this sounds good to you: Welcome to Trulie Oaks, Your Wooded Retreat!

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.