
Vacation rentals in Bloomington
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Top-rated vacation rentals in Bloomington
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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.
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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.
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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.
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Cozy Cabin by the Pond
Primary guest must be 21+ Quiet country location to relax & enjoy. Just 9 miles west of Dubuque, near Wineries, Heritage Trail, Sundown Mountain Resort. Primary guest must be 21+ to book. Cozy cabin & 1/4 acre pond. We're sure you’ll love this space as much as we do. Not suitable for children under 12, we strictly enforce no children or pets, and must be 21+ to book. Outdoor space, gas grill, gas fire pit. Fully stocked cabin, with breakfast items included for you to enjoy at your leisure.
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Peaceful Driftless A-Frame
Nestled among two acres in the rolling hills and lush greenery of the Driftless Area, this A-frame cabin stands as a serene retreat, blending harmoniously with its natural surroundings. The decor is a blend of modern comforts and rustic elements, with comfortable furnishings. Seated in the heart of the Kickapoo valley, there's no shortage of class 1 trout streams near by, public hunting easements, UTV trails, hiking, canoeing and easy access to all of the wonderful amenities the area offers.
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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
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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.
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**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
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Suite 1 – Lydia's Loft
This unit is brand new construction for the summer of 2025 featuring a living area with a large projection screen and a fully equipped kitchen with bar and smart TV. The bathroom includes a corner shower and washer/dryer. All sleeping is above in the large open loft with one queen bed, full/twin bunk and twin bed to comfortably sleep up to six. This unit also has an outside dining area/patio. To see the other attached unit, click here: airbnb.com/h/310lincolnslodge
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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.
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The Cottage at Streamwalk
Located off the beaten path in a beautiful pristine valley, this 1 bed, 1 ½ bath cottage offers high end furnishings with a vintage flair modeled after a true english stone cottage. The cottage offers miles of private walking trails on 100 private acres along the renowned Big Green trout stream. Our small highland cow herd roams the pastures, making it feel like you truly are in the Scottish Highlands.
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Crooked Creek - Rustic Cabin
Rustic Cabin – Driftless Wisconsin Getaway 🏞️🔥 Discover a charming Amish-style cabin tucked into a quiet valley of Wisconsin’s scenic Driftless Region. Surrounded by tree-lined bluffs, a meandering creek, and open green spaces, this cabin is perfect for couples seeking a romantic escape or outdoor adventurers looking for a comfortable base for hiking, kayaking, fishing, or scenic motorcycling.
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Popular amenities for Bloomington vacation rentals
Other great vacation rentals in Bloomington

Rustic 3Bed 2Bath Home near Downtown PDC
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Historic Charm in the Heart of McGregor, Iowa
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Pleasant Ridge Retreat
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Eagle View Lodge - 1850's Log Cabin w/ Hot Tub
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River Bluff Retreat-Hot tub & game room
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Wood Duck Inn
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Firefly Cottage @ River of Lakes
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The Driftless A-Frame - pet friendly
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Destinations to explore
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- House on the Rock
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- Wyalusing State Park
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- Effigy Mounds National Monument
- National Mississippi River Museum & Aquarium
- US Grant Home State Historic Site
- American Players Theatre
- Field of Dreams Movie Site
- Galena Cellars Vineyard
- Fenelon Place Elevator Company
- Diamond Jo Casino





