Vacation rentals in Orangeville

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Top-rated vacation rentals in Orangeville

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Superhost

Home in Argyle

4.89 out of 5 average rating, 257 reviews

Relaxing 3 Bedroom Cabin with Hot Tub and Scenery

Tucked away in the rolling hills of Southern Wisconsin sits a little log home ready for your arrival. Hand built by the caretaker and his family; the Braezel Branch Retreat is named after the stream that runs through the valley. Relax with the whole family in this two-bedroom, two-bathroom cabin with a comfortable open floor plan. Wander through the beautiful walking trails and enjoy the view of the valley from the large front porch. There is also local tubing, kayaking, golfing and wineries.

Top guest favorite

The exterior of a rustic studio is illuminated at night, showcasing wooden siding and a green metal roof. Soft warm light glows from several windows, while a kayak is mounted on the wall. Lush greenery surrounds the entrance, creating a serene outdoor space.

Guesthouse in Mount Horeb

4.96 out of 5 average rating, 607 reviews

Cool, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful one-room loft-style space featuring tall ceilings, an entire wall of sliding glass doors, kitchenette, piano, and an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Well-behaved dogs, included in your reservation, must be leashed when outside.

Top guest favorite

A vibrant streetscape features a charming mix of historic buildings, with a focus on the storefronts below. The ground floor includes a cozy café adorned with bright flowers and outdoor seating, while the upper levels showcase colorful facades and decorative window details.

Loft in Monroe

4.99 out of 5 average rating, 175 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

Home in Freeport

4.98 out of 5 average rating, 185 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 favorite

An exterior view of an old schoolhouse is captured, showcasing its classic architecture. A group of children stands in front, dressed in period attire. The surrounding trees add a natural backdrop, enhancing the historic character of the building.

Place to stay in Brodhead

4.98 out of 5 average rating, 160 reviews

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Top guest favorite

A small cottage is illuminated by warm outdoor lighting, creating a welcoming ambiance. A gravel path leads up to the door, surrounded by trees. Two white chairs are positioned nearby, inviting relaxation amid the tranquil woodland setting.

Tiny home in Darlington

4.98 out of 5 average rating, 756 reviews

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

Top guest favorite

An inviting living area showcases wooden beams and cozy furnishings. A plush chair and a wooden bench are positioned near a decorative fireplace, while natural light streams in through the sliding glass doors leading to the outdoor deck.

Cabin in Savanna

4.96 out of 5 average rating, 301 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

A spacious living area features a large sectional sofa in muted tones, complemented by a rustic wooden coffee table on a light-colored area rug. Exposed brick walls provide texture, while modern lighting fixtures and artwork contribute to the inviting atmosphere.

Apartment in Monroe

5 out of 5 average rating, 241 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 calm lake is depicted, reflecting greenery from surrounding trees under a clear blue sky. The still water creates a mirror-like effect, enhancing the natural beauty of the landscape, while the lush foliage provides a sense of tranquility.

Cabin in Brodhead

4.88 out of 5 average rating, 107 reviews

Cozy Cabin on Decatur Lake

Relax in this cozy cabin on the lake. Fish, hike or even swim (after a short canoe/kayak paddle); just like being Up-North without the drive! Use our canoe or kayaks or bring your own. Cook indoors or out. Near Sugar River Trailhead, Headgates Park and Three Waters Reserve. A few miles away from tubing on the Sugar River. An hour from Madison and 30 minutes from Beloit, Monroe or Janesville. Previously listed by Betty and under her same great management!

Top guest favorite

A clean white toilet is presented from a top view. The toilet features a smooth ceramic finish, with an instructional label visible above the bowl. The surrounding area includes light-colored tiles that enhance the overall cleanliness of the space.

Guest suite in Freeport

5 out of 5 average rating, 100 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. The apartment has a 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 2 Twin XL that JOINS TO MAKE A 2nd KING both w/memory foam mattresses and 3 additional Twin XL beds. Free Washer/Dryer in apt.

Guest favorite

An outdoor deck offers scenic views of the Mississippi River. The space is furnished with a round dining table and four comfortable chairs. A grill is positioned nearby, surrounded by lush greenery and trees, enhancing the natural setting of the cabin.

Tiny home in Thomson

4.87 out of 5 average rating, 437 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

A wooden table is set with a bottle of white wine and a glass, alongside a platter containing slices of cheese and fresh strawberries and blueberries. Lush greenery is seen in the background, enhancing the outdoor dining experience.

Farm stay in Monroe

5 out of 5 average rating, 152 reviews

The Dairy at the Wegmueller Farm

Welcome! You are about to experience life on an active 4th-generation farm nestled in the rolling hills of Green County. Meet the cows, feed the pigs, befriend a horse, or just enjoy the relaxing and peaceful serenity of rural Wisconsin farm life. Located less than five miles from Monroe, this home away from home is close enough to all that Monroe & the surrounding community has to offer, but still has room to stretch your legs.

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Popular amenities for Orangeville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Orangeville

Guest favorite

Cabin in Pearl City

4.92 out of 5 average rating, 37 reviews

Getaway cabin w/loft & firepit @The Rustic Retreat

MiriamRating, 5 stars1 week ago

We had an amazing time at Phil’s place. The cabin had anything we needed and was surrounded by nature. Phil was always very responsive and helpful.

Guest favorite

A compact kitchen appliance is displayed on a blue countertop, featuring dual glass doors and an illuminated control panel. A black kettle is positioned alongside it, providing additional functionality to the kitchen space.

Apartment in Freeport

5 out of 5 average rating, 19 reviews

Walk everywhere in downtown Freeport.

LukeRating, 5 stars2 weeks ago

A fantastic price for a convenient location! The inside is spacious with all the amenities you could need. The outside can look a bit uninviting, but the room itself, as well as Judy, were fantastic!

Top guest favorite

A sliding glass door leads to a balcony with a railing, offering views of lush greenery and open fields under a clear blue sky. Natural light brightens the entryway, enhancing the connection to the outdoor landscape.

Home in Blanchardville

4.93 out of 5 average rating, 40 reviews

Coffee with a View

JasonRating, 5 stars4 days ago

Couldn't have asked for more. Fantastic property and a responsive, friendly host. He even reached out to offer early check-in. We'll be back! From the wife: One of the best stays we’ve had! The host was super responsive—when our kids lost a ball, Kevin showed up with 2 new ones AND chalk. The cabin was spotless, with cozy couches, blackout curtains, comfy beds, & blankets everywhere. We loved the smart fridge for music, strong Wi-Fi, & the heated toilet seat (game changer!). Shower had great pressure, towels were plush & smelled amazing & the AC kept us cool. Porch felt like a villa in Costa Rica, especially in the rain. Early check-in, a generous welcome gift & even dog bags for our pups. Massage chair, grill, and space to spread out—we will DEFINITELY be back again, next time without our crazy children!

Top guest favorite

Home in Monroe

4.96 out of 5 average rating, 26 reviews

Historic Country Farmhouse for Any Season!

RyanRating, 5 stars5 months ago

We stayed at Susan’s beautiful farmhouse during the Christmas holiday. It was everything we were hoping for and more. Susan is wonderful to work with, responsive and helpful. The home is gorgeous with so much history and the feeling of love from many years of family. The decorations for Christmas were wonderful and enhanced the stay that much more. We would love to go back in the Spring or again for the holidays. Downtown Monroe is very close by. It’s a quaint and cozy area with shops, restaurants and the ability to walk and enjoy it. Looking forward to going back!

Top guest favorite

A recreation area features comfortable black leather seating, including a spacious sofa and reclining chair. A sleek coffee table is centered in the space, which is adorned with light-colored flooring. The walls are decorated with thematic artwork, enhancing a relaxed atmosphere.

Home in South Wayne

4.98 out of 5 average rating, 85 reviews

Welcome to the "Bat Cave"!

BrittanyRating, 5 stars1 week ago

It was an adorable house and just what we needed for our Father’s Day weekend away. It was conveniently located to New Glarus where we attended the BBC festival. Haley was a great host and we loved the sensitive skin option for the shower as we have eczema. It was all the little touches from energy drinks and protein shakes that really made it special.

Top guest favorite

An aerial view captures the cottage nestled among lush trees on a hillside, with expansive green fields beyond. A vibrant sunset bathes the landscape in golden hues, enhancing the serene and secluded atmosphere of the property amidst the natural surroundings.

Cottage in Saint Donatus

4.99 out of 5 average rating, 96 reviews

Gorgeous Views, Sweeping Valley, Amazing Sunsets

CarolynRating, 5 stars2 weeks ago

This was the nicest rental I have ever stayed in! The quality of everything was top of the line, and Joe and Kelly spared absolutely NO expense to make this space truly fabulous. From the quality of the appliances and furniture, to the beautiful details in every room, to the handwritten card welcoming us and local chocolate and wine (which were delicious)...there was absolutely not a thing that could have made our stay better (other than staying longer!). We saw rabbits, tons of birds, turkey vultures, hawks, deer, chipmunks, and squirrels, and enjoyed seeing the animals in their natural environment. What a spectacular view! My boyfriend (whose birthday we were celebrating) said it was the nicest house he's ever been in, period. If you're a fan of FL Wright, you will adore this house and all the details that show the love and appreciation for his work. We will most definitely come back, it was worth every penny! Thank you, Joe and Kelly, for being as amazing as your cabin! :)

Guest favorite