
Holiday rentals in Bloomington
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Bloomington
Guests agree: these stays are highly rated for location, cleanliness and more.

Larsen Rustic Secluded Log Cabin W/Outdoor Hot Tub
Secluded cabin hike the trails to the cave and ponds. Close to trout fishing stream or Mississippi for fishing. Bring you UTV and ride the private trails $30 per driver and 10 per passenger or rent an UTV 300.00 per day Approx 15 miles from Priarie Du Chein, close to canoe outposts for the Kickapoo, Wisconsin river. Has a gas ,charcoal grill,fire pit, pool table, fooseball, ping pong table. Smart TV Private UTV trails are closed Oct 15th thru mid Jan for hunting. Access to public UTV trails.
FamilyLocationComfort
4.79 out of 5 average rating, 473 reviews
River Trails Cottage
Have fun with the entire family or a group of friends in a quiet peaceful setting. The cabin sits on 2 acres and attaches to 8700 acres of public land that is open to hunting, hiking and abundant with wildlife which makes this property great for the outdoor enthusiast. The property is 6/10 mile from a public boat landing where you can fish, kayak or canoe the Wisconsin River. There are multiple parks relatively close that offer excellent hiking trails. Direct access to miles of ATV/UTV trails.
FamilyLocationAmenities
5.0 out of 5 average rating, 66 reviews
The Bunk House
Book your stay with The Bunk House! Great for large groups, cozy weekends or family getaways. Features include free WiFi, TV/DVD player/DVDs and board games available, fully furnished kitchen, bathrooms, extra makeup stations and free laundry. The Bunk House is conveniently located within walking distance of beautiful downtown Prairie Du Chien~Great bars, restaurants, shopping, farmers/flea markets, water fun, historical sites and so much more. I’d love to help make your stay a memorable one!
FamilyLocationBack garden
4.93 out of 5 average rating, 189 reviews
River Bluff Retreat-Hot tub & game room
Relax with the whole family at this peaceful retreat just 5 miles from historic Guttenberg, Iowa. Situated on a bluff overlooking the majestic Mississippi River, you'll love the amazing view. This private property offers plenty of space with room for your boats and ATV's. Gather in the large game room, or spread out across multiple living areas. Enjoy the high-speed Starlink internet and complimentary access to YouTube TV and NFL Network. This is the perfect getaway for groups up to 13.
ValueLocationLayout
4.95 out of 5 average rating, 43 reviews
The Lancaster House
Welcome to The Lancaster House, a beautifully remodeled 4-bedroom, 2-bath retreat that sleeps up to 11 guests comfortably. Enjoy the spacious back yard, patio and off street parking. Ideal for family vacation, a local wedding, a work trip, or just passing through Wisconsin's stunning Driftless Region—this is the perfect spot to relax, recharge, and reconnect. Near City Park & Lancaster’s Pool, Grant County Fairgrounds, School, Golf course, Downtown, Hiking, boating, fishing & sightseeing.
LocationFamilyCondition
5.0 out of 5 average rating, 25 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.
FamilyValueBathroom
4.98 out of 5 average rating, 243 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
FamilyLocationPets
4.89 out of 5 average rating, 239 reviews
Plum Creek Cabin: Nature Lover’s Retreat +HOT TUB
Relax at a charming cabin nestled on a farm in the heart of Plum Creek Valley, offering picturesque views and a class 1 trout stream on property. This idyllic getaway is a mix of woods and pasture, perfect for immersing yourself in the beauty of nature. Access to nearby UTV/snowmobile trails. Whether you’re here for outdoor activities or simply to unwind in a serene setting, this cabin is an ideal retreat for families, friends and outdoor enthusiasts.
LocationFamilyHospitality
4.94 out of 5 average rating, 31 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.
LocationFamilySleep quality
4.98 out of 5 average rating, 113 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.
LocationValueParks
4.93 out of 5 average rating, 228 reviews
Valley Mills Miller's Cottage
Welcome to Valley Mills Miller's Cottage, where the beauty of "Mother Nature" surrounds you. Built six years after Iowa became a state in 1847, it is located in a remote picturesque valley containing Buck Creek Trout Stream. It is completely surrounded by wooded Bluffs, known as "Cold Slopes". With its two acre park like area, it is an ideal place for families to let their Kids/pets freedom to roam.
ValueFamilyCleanliness
4.7 out of 5 average rating, 158 reviews
Secluded Bardo Retreat w/ Hot Tub + View
Find Your Stillness | Omega Ridge Retreat on 6 Private Acres This one-of-a-kind property features a brand new Barndominium, perfect for couples’ getaways, family gatherings, small retreats, or anyone longing to unwind in nature without sacrificing comfort. This area is great for hiking hunting fishing, canoeing side-by-side riding & near the historic town of Guttenberg just 6 miles away.
FamilyLocationCleanliness
5.0 out of 5 average rating, 24 reviewsPopular amenities for Bloomington holiday rentals
Other great holiday rentals in Bloomington

The Getaway
LocationValueBathroom
4.96 out of 5 average rating, 85 reviews
Grandma’s Guttenberg Getaway
LocationFamilyIndoor spaces
5.0 out of 5 average rating, 30 reviews
Roofscape Retreat
FamilyLocationOutdoor spaces
5.0 out of 5 average rating, 36 reviews
Victorian Home one block from Mississippi River!
FamilyLocationHiking
4.99 out of 5 average rating, 83 reviews
The Lakeside Inn
LocationParksAmenities
4.9 out of 5 average rating, 10 reviews
August & Alma’s
FamilyLocationIndoor spaces
5.0 out of 5 average rating, 54 reviews
Rustic 3Bed 2Bath Home near Downtown PDC
FamilyLocationBathroom
4.91 out of 5 average rating, 43 reviews
Peaceful Driftless A-Frame
FamilyLocationGetting around
4.97 out of 5 average rating, 73 reviewsDestinations to explore
- Chicago Holiday rentals
- St. Louis Holiday rentals
- Minneapolis Holiday rentals
- Milwaukee Holiday rentals
- Omaha Holiday rentals
- Traverse City Holiday rentals
- Des Moines Holiday rentals
- Saint Paul Holiday rentals
- Downtown Chicago Holiday rentals
- Duluth Holiday rentals
- Sioux Falls Holiday rentals
- Grand Rapids Holiday rentals
- House on the Rock
- Backbone State Park
- Sundown Mountain Resort
- Wyalusing State Park
- Governor Dodge State Park
- Field of Dreams Movie Site
- Effigy Mounds National Monument
- National Mississippi River Museum & Aquarium
- American Players Theatre
- US Grant Home State Historic Site
- Galena Cellars Vineyard
- Fenelon Place Elevator Company





