Holiday houses in Bloomington

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Top-rated holiday rentals in Bloomington

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Top Guest favourite
A charming farmhouse is nestled among lush greenery, surrounded by tall trees. The two-story structure features a gabled roof and a covered front porch. Natural landscaping, including shrubs and grass, frames the house, creating a serene and private atmosphere amidst the forested hills.
Cabin in Gays Mills
4.98 out of 5 average rating, 347 reviews

Driftless Region Cabin/ Stream and Sauna

Settle into a quaint farmhouse nestled in a valley in the rolling, forested hills of the Driftless Region. Start your day with a cup of local coffee on the front porch. Go on a long walk or bike ride, then return to the cottage to cook, play board games, listen the record collection or visit Viroqua (25 minutes) for a farm-to-table 5-star dinner, or check out local music. Build a warm fire outdoors/ warm up by the gas stove indoors, or go down to the stream for a sauna by the cool water creek.

Top Guest favourite
A serene view of a tranquil pond reflects a cozy cabin surrounded by greenery. Soft grasses frame the foreground, while the sky showcases gentle clouds. The cabin features a covered porch, enhancing the peaceful ambiance of the quiet country location.
Cabin in Durango
4.99 out of 5 average rating, 320 reviews

Cozy Cabin by the Pond

Quiet, private country location to relax and unwind. 9 miles west of Dubuque, close to Wineries, Heritage Trail, Sundown Mountain Resort. Cozy cabin and quarter acre pond. Sun yourself on the patio, or nap in the shade of the covered porch. We're sure you will love this space as much as we do. Not suitable for children under 12, we strictly enforce no children and no pets. Outdoor relaxing space, gas grill. Fully stocked cabin, with breakfast items included for you to enjoy at your leisure.

Guest favourite
A quaint blue house is shown from the side, surrounded by lush green grass. A wooden fence partially outlines the property, with a few flowering plants positioned along the edge. Clear skies and sunlight illuminate the exterior, highlighting its welcoming presence.
Home in Prairie du Chien
4.98 out of 5 average rating, 153 reviews

Ohio Street Retreat- hot tub, massage chair, pool

After a fun day in The Driftless Area, come relax and unwind in Prairie du Chien. Beautifully decorated 2 bedroom home with a spacious kitchen, large island, dishwasher, washer/dryer & 5' walk in shower. We supply all cooking/baking items/utensils so all you need are your food, drinks and ingredients. Full high-speed internet with smart TVs in both bedrooms and living room. Outdoor pool (seasonal), hot tub and massage chair. We love dogs too, so we provide a dog run (there is a pet fee).

Top Guest favourite
A lush green landscape rises just beyond a calm river, with a small collection of buildings visible along the shore. The architecture varies, featuring both traditional and modern designs, under a sky filled with fluffy clouds.
Apartment in Clayton
4.93 out of 5 average rating, 164 reviews

Cozy Apartment Steps from the Mighty Mississippi

Disconnect from the daily grind and enjoy a getaway in this welcoming one bedroom apartment, steps away from the Mighty Mississippi. Located in Clayton, Iowa, Located within walking distance of two delicious restaurants and a boat launch., and only 1/2 hour from the Casino Queen, local wineries, Pikes Peak State Park, as well as the historic communities of Elkader, IA and Prairie Du Chien, WI. Need more space? I also offer a two bedroom apartment: www. airbnb. com/rooms/43979345

Top Guest favourite
The log cabin exterior is surrounded by lush greenery and tall grasses. A welcoming porch is highlighted by a wooden rocking chair. Natural light accentuates the cabin's rustic wooden finish, and a roof overhang provides shade to the entryway.
Cabin in Potosi
4.98 out of 5 average rating, 218 reviews

Unplug and get back to nature

The log cabin was built as a place to unwind, relax, and truly unplug. Nestled among 15 acres of rolling hills, the cabin can serve as a place to hunker down and read three novels, or a home base for hiking, cycling and putting the nature back in your life. Be advised, there is NO television and that’s for good reason. Cook, drink, eat, play, relax and refresh yourself. Wake up to the songs of birds and listen to the owls at night while you’re warming yourself around a bonfire.

Superhost
A vibrant orange cabin is set against a backdrop of trees and gentle hills. Large windows and a front door reveal a welcoming appearance. A winding gravel path leads to the entrance, surrounded by lush green landscaping and natural foliage.
Cabin in Bagley
4.89 out of 5 average rating, 207 reviews

**Cozy & Dog Friendly** Rustic Cabin Retreat

Relax and recharge at this country getaway which is tucked amongst trees and the rolling hills. Surround yourself with nature while also having easy in and out access! This makes it a breeze to come and go as you please and explore all southwest Wisconsin has to offer! Ready for the whole family to enjoy, along with their furry friends. *9 minute drive to Wyalusing State Park *10 minute drive to Bagley / Wyalusing Public Beach *16 minute drive to Prairie du Chien

Top Guest favourite
A welcoming living area features a comfortable sofa and a wooden coffee table. Large windows provide a scenic view of the landscape and river, allowing natural light to fill the space. A TV is mounted above a stone fireplace, creating a cozy atmosphere.
Home in Dubuque
5 out of 5 average rating, 180 reviews

Home by the River

Situated alongside the Mississippi River, wildlife abounds in every season. With eagles nesting nearby, there is always something new to see from the beautiful sunrises, cruise ships passing by, and watching the commerce of the barges and railroad right out the front window! This home has been recently refurbished and sits at the edge of our 15 acres. You can see us and visit with us if you like, or you can maintain privacy 10 acres away!

Top Guest favourite
A cozy three-season room features large windows that provide a view of the Mississippi River. Two grey, tufted sofas are positioned around a decorative area rug. A blanket drapes over one sofa, and a framed wall art piece with the text 'THIS IS THE LIFE' adds a cheerful touch.
Home in Clayton
4.98 out of 5 average rating, 101 reviews

Clayton Riverway House~ River front home

Sit back and relax in a home that is directly on the Mississippi River in Clayton, Iowa! Enjoy watching the trains, barges and river traffic, fishing off of the private or public dock, or spending time with your friends and family in this quaint river town. Northeast Iowa has many activities to enjoy, such as boating, fishing, hiking, hunting, antiquing. Riverway House is the perfect place to stay while enjoying the beauty of Clayton County.

Top Guest favourite
The vibrant red home features multiple large windows, allowing natural light to enhance the interior spaces. A spacious deck extends from the house, bordered by trees and rocky terrain, creating a picturesque setting amidst the lush surroundings.
Home in McGregor
5 out of 5 average rating, 100 reviews

#StayBluffside: Mississippi River Oasis-> McGregor

The Bluffside Retreat is an ideal location for the adventure seekers who want a unique and private experience that is still close to all the action. The home is situated alongside the bluff on a private & partially wooded lot within walking distance of the Mississippi River, historic downtown McGregor and a Pikes Peak State Park TrailHead. It is a charming “home away from home” that has all the amenities for a memorable vacation stay.

Guest favourite
A charming cabin is positioned on elevated ground, featuring a welcoming porch adorned with wooden railings. Surrounding greenery offers shade, while a paved pathway leads up to the entrance. The structure boasts large windows, allowing natural light to fill the interior.
Cottage in Lancaster
4.93 out of 5 average rating, 216 reviews

Grant River Getaway

80+ acres of Wisconsin Driftless beauty highlighted by private access to the Grant River. Our land is perfect for snowshoeing, hiking, and fishing. The location is on an ATV/UTV route and is great for bicycling, walking, and scenic motorcycle trips. Discover southwest Wisconsin's unique attractions and scenery while enjoying our quaint, cozy cabin. There's plenty to do without having to leave the property.

Guest favourite
A rustic cabin with a green roof is nestled among trees, set on a winding dirt path. Silos are visible in the background, indicating a rural setting. A portable restroom is positioned nearby, and natural greenery surrounds the area, enhancing the secluded feel.
Cabin in Boscobel
4.91 out of 5 average rating, 190 reviews

Windy Ridge Retreat Secluded Rustic Cabin

The Windy Ridge Retreat is a rustic cabin that is tucked away on a beautiful ridge. It is secluded and cozy. Rough trail hiking is available from the cabin. A short drive will take you to rivers, beaches, trout streams to fish, canoe, boating, tubing and swimming. Many nice areas around us to sight see or just sit back and relax.

Top Guest favourite
A modern cottage exterior features natural stone walls and expansive glass panels reflecting the warm colors of sunset. Surrounded by trees, the structure integrates with the landscape, showcasing a blend of contemporary architecture and nature.
Cottage in Saint Donatus
4.99 out of 5 average rating, 112 reviews

Gorgeous Views, Sweeping Valley, Amazing Sunsets

If you love Frank Lloyd Wright you will love this cottage. Taking over 2.5 years to build in a secluded cedar woods, surrounded by bluffs and perched on top of the landscape. The original Frank Lloyd Wright cottage (Seth Petersen) is the inspiration to build this cottage.

Popular amenities for Bloomington holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Grant County
  5. Bloomington