Bloomington Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Bloomington vacation rentals

Property grounds
Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
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 ￥13,756
￥24,191 total
includes taxes & fees
Dec 23 - Dec 24
Crooked Creek - Relaxation Cabin
Exterior
Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
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 ￥16,335
￥29,801 total
includes taxes & fees
Dec 23 - Dec 24
Crooked Creek - Serenity Cabin
TV, fireplace
Paint Creek Lodge ... 5 Bedroom A-Frame Log Cabin W/Hot Tub & Swimming Pond

Paint Creek Lodge ... 5 Bedroom A-Frame Log Cabin W/Hot Tub & Swimming Pond

Paint Creek Lodge ... 5 Bedroom A-Frame Log Cabin W/Hot Tub & Swimming Pond
Harpers Ferry
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
Exterior
Crooked Creek - Rustic Cabin

Crooked Creek - Rustic Cabin

Crooked Creek - Rustic Cabin
Boscobel
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 ￥13,756
￥25,098 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Crooked Creek - Rustic Cabin
Terrace/patio
Ohio Street Retreat-hot tub, massage chair, pool

Ohio Street Retreat-hot tub, massage chair, pool

Ohio Street Retreat-hot tub, massage chair, pool
Prairie du Chien
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

Mr. Rogers River View

Mr. Rogers River View
Guttenberg
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 ￥17,747
￥27,829 total
includes taxes & fees
Dec 23 - Dec 24
Mr. Rogers River View
Interior
Historic Sadie's Log Cabin

Historic Sadie's Log Cabin

Historic Sadie's Log Cabin
McGregor
10.0 out of 10, Exceptional, (5)
"Pocket City Pub, Backwoods Bar & Grill"
United States
Curtis
The price is ￥21,699
￥27,837 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Historic Sadie's Log Cabin
Interior
Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
2.0 star property
Fennimore
The price is ￥18,930
￥26,628 total
includes taxes & fees
Dec 23 - Dec 24
Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fridge, microwave, oven, stovetop
Fritz’s Farmhouse.. Country getaway.

Fritz’s Farmhouse.. Country getaway.

Fritz’s Farmhouse.. Country getaway.
Guttenberg
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 ￥19,719
￥36,396 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fritz’s Farmhouse.. Country getaway.
Property grounds
Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park

Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park

Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park
Bagley
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!

Mississippi River Front Property with amazing views!

Mississippi River Front Property with amazing views!
Harpers Ferry
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!
Fridge, microwave, oven, stovetop
Historic Victorian Apartment

Historic Victorian Apartment

Historic Victorian Apartment
McGregor
10.0 out of 10, Exceptional, (6)
"Really cool place in a cute little town!"
United States
Nicholas M.
The price is ￥32,962
￥40,450 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Historic Victorian Apartment
Dining
Wisconsin Log Cabin Lodge | Sleeps 16

Wisconsin Log Cabin Lodge | Sleeps 16

Wisconsin Log Cabin Lodge | Sleeps 16
Cassville
10.0 out of 10, Exceptional, (2)
"Amazing cabin in the woods for a weekend getaway. "
United States
Michael D.
The price is ￥157,592
￥252,554 total
includes taxes & fees
Dec 23 - Dec 24
Wisconsin Log Cabin Lodge | Sleeps 16
4 bedrooms, iron/ironing board, internet, bed sheets
Wisconsin Luxury Log Mansion | Sleeps 15

Wisconsin Luxury Log Mansion | Sleeps 15

Wisconsin Luxury Log Mansion | Sleeps 15
Cassville
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 19 hours 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:

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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.