Bloomington Vacation Rentals

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Check prices for these dates

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Bloomington vacation rentals

Property grounds
Crooked Creek - Relaxation Cabin

Cabin in Boscobel

Crooked Creek - Relaxation Cabin
9.8 out of 10, Exceptional, (8)
"The property was very comfortable and quiet and nicely decorated. I loved our stay and would choose a relaxation cabin again."
United States
Constance L.
The price is ￥13,682
￥24,061 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Crooked Creek - Relaxation Cabin
TV, books
Crooked Creek - Serenity Cabin

Cabin in Boscobel

Crooked Creek - Serenity Cabin
10.0 out of 10, Exceptional, (11)
"Everything from booking, cleanliness, amenities and checking out were excellent. The front porch was wonderful!"
United States
Susan M B.
The price is ￥16,247
￥29,640 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Crooked Creek - Serenity Cabin
Property grounds
Paint Creek Lodge ... 5 Bedroom A-Frame Log Cabin W/Hot Tub & Swimming Pond

Cabin in Harpers Ferry

Paint Creek Lodge ... 5 Bedroom A-Frame Log Cabin W/Hot Tub & Swimming Pond
6.8 out of 10, (3)
"Very quiet and peaceful location!"
United States
Kirk W.
The price is ￥10,648
￥47,970 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Paint Creek Lodge ... 5 Bedroom A-Frame Log Cabin W/Hot Tub & Swimming Pond
TV
Crooked Creek - Rustic Cabin

Cabin in Boscobel

Crooked Creek - Rustic Cabin
9.6 out of 10, Exceptional, (8)
"It was a beautiful, solidly built, cozy cabin in a very pretty location. Perfect getaway spot. Very kind and helpful host! "
United States
Lindsay W.
The price is ￥13,682
￥24,963 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Crooked Creek - Rustic Cabin
Fridge, microwave, oven, stovetop
Ohio Street Retreat-hot tub, massage chair, pool

Vacation Home in Prairie du Chien

Ohio Street Retreat-hot tub, massage chair, pool
10.0 out of 10, Exceptional, (71)
"We had a wonderful weekend enjoying all the parks the area has to offer. The pool and massage chair were a nice added perk to the property, especially after hiking in the parks."
United States
Kristine C.
The price is ￥19,593
￥32,604 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Ohio Street Retreat-hot tub, massage chair, pool
Property grounds
Mr. Rogers River View

Apartment in Guttenberg

Mr. Rogers River View
9.6 out of 10, Exceptional, (39)
"It was a cute place to stay. The river view was awesome. Great walking distance for a lot of places. Our bed wasn’t the most comfortable. "
United States
RICHARD
The price is ￥17,651
￥27,678 total
includes taxes & fees
Dec 28 - Dec 29
Mr. Rogers River View
Exterior
Historic Sadie's Log Cabin

Cabin in McGregor

Historic Sadie's Log Cabin
10.0 out of 10, Exceptional, (5)
"Pocket City Pub, Backwoods Bar & Grill"
United States
Curtis
The price is ￥22,241
￥28,424 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Historic Sadie's Log Cabin
Interior
Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Apartment in Fennimore

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
2.0 star property
The price is ￥18,828
￥26,485 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Terrace/patio
Fritz’s Farmhouse.. Country getaway.

Vacation Home in Guttenberg

Fritz’s Farmhouse.. Country getaway.
10.0 out of 10, Exceptional, (74)
"Love the house, it was really neat! Lots of room to park boats. Will stay again!"
United States
Timothy D.
The price is ￥19,613
￥37,079 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Fritz’s Farmhouse.. Country getaway.
Property grounds
Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park

Cottage in Bagley

Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park
9.4 out of 10, Exceptional, (40)
"Great cozy place near the river!"
United States
Clint P.
The price is ￥22,716
￥50,095 total
includes taxes & fees
Dec 25 - Dec 26
Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park
Property grounds
Mississippi River Front Property with amazing views!

Cottage in Harpers Ferry

Mississippi River Front Property with amazing views!
9.0 out of 10, Wonderful, (12)
"Great location, limited amenities "
United States
Joel T.
The price is ￥55,213
￥89,224 total
includes taxes & fees
Dec 29 - Dec 30
Mississippi River Front Property with amazing views!
TV
Historic Victorian Apartment

Apartment in McGregor

Historic Victorian Apartment
10.0 out of 10, Exceptional, (6)
"Really cool place in a cute little town!"
United States
Nicholas M.
The price is ￥32,962
￥41,687 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Historic Victorian Apartment
Property grounds
Wisconsin Log Cabin Lodge | Sleeps 16

Vacation Home in Cassville

Wisconsin Log Cabin Lodge | Sleeps 16
10.0 out of 10, Exceptional, (2)
"Amazing cabin in the woods for a weekend getaway. "
United States
Michael D.
The price is ￥194,821
￥296,991 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Wisconsin Log Cabin Lodge | Sleeps 16
Interior
Wisconsin Luxury Log Mansion | Sleeps 15

Vacation Home in Cassville

Wisconsin Luxury Log Mansion | Sleeps 15
10.0 out of 10, Exceptional, (3)
"Once again the owner (Steve) went above and beyond making our family right at home. This was our 4th year here and already making plans for next year. Thanks again for the 5 star weekend. "
United Kingdom
Bam Bam D.
The price is ￥194,821
￥301,151 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Wisconsin Luxury Log Mansion | Sleeps 15
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bloomington Hotel Reviews

Windsor Place Inn

Windsor Place Inn

10/10 Excellent
"breakfast was put out early. which was great"
Troy 1-night trip
Posted 1 day ago
Windsor Place Inn

Find out more about Bloomington

Search for holiday rentals in Bloomington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bloomington using one of the methods below:

  • View our selection of featured holiday rentals in Bloomington
  • Use the map to find apartments and other holiday homes in the Bloomington neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Bloomington while they last

Look no further and take a look at our great range of rental properties in Bloomington!

Frequently asked questions

Can I find vacation rentals in Bloomington?

Yes, there are vacation rentals close to top sights in Bloomington, or you can go with a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Bloomington?

Ohio Street Retreat-hot tub, massage chair, pool: Visitors like this Bloomington vacation home rental. It offers a balcony, a hot tub, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Bloomington?

While exploring the area, visit family-friendly sights like Charles Wacouta Aquatic Park, or get outside and enjoy nature at Grant River. Jays Lake and Big Springs are a couple of places you'll find in the larger area.

What are vacation rentals like in Bloomington?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Bloomington. Vacation rentals provide amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a small group gathering.