Photo by Jim Watkins

Jackson County Holiday Rentals

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Our top choices for Jackson County holiday rentals

Outdoor dining
Hoosier National Hideaway

Apartment in Seymour

Hoosier National Hideaway
9.8 out of 10, Exceptional, (51)
"Loved everything about it, secluded, quiet romantic "
United States
John
Hoosier National Hideaway
Exterior
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

Holiday Home in Vallonia

Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
2.0 star property
10.0 out of 10, Exceptional, (14)
"Excellent place to stay. Everything was absolutely amazing. "
United States
Jimmy
The price is HK$1,366
HK$2,340 total
includes taxes & fees
1 Jan - 2 Jan 2026
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
Exterior
Postcard Cabins Brown County, Outdoor Collection by Marriott Bonvoy

Cabin in Columbus

Postcard Cabins Brown County, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.4 out of 10, Exceptional, (60)
"It was amazing stay!"
United States
Anas
The price is HK$589
HK$1,035 total
includes taxes & fees
6 Jan - 7 Jan 2026
Postcard Cabins Brown County, Outdoor Collection by Marriott Bonvoy
Fountain
Salt Creek Golf Retreat

Aparthotel in Nashville

Salt Creek Golf Retreat
3.5 star property
9.2 out of 10, Wonderful, (177)
"Clean room and friendly staff!"
United States
Eric
The price is HK$1,244
HK$1,493 total
includes taxes & fees
7 Jan - 8 Jan 2026
Salt Creek Golf Retreat
Smart TV, books
Charming 2-bedroom house with WiFi, AC in superb Bedford

Holiday Home in Bedford

Charming 2-bedroom house with WiFi, AC in superb Bedford
10.0 out of 10, Exceptional, (6)
"The property was clean, cozy and close to town and shops. It supplied everything we needed. "
United States
Jodee K.
The price is HK$630
HK$1,646 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 2-bedroom house with WiFi, AC in superb Bedford
Exterior
Cozy Tiny House in Scottsburg

Holiday Home in Scottsburg

Cozy Tiny House in Scottsburg
9.6 out of 10, Exceptional, (4)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is HK$642
HK$1,372 total
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy Tiny House in Scottsburg
Individually decorated, individually furnished, iron/ironing board
Treetop Retreat

Cabin in Nashville

Treetop Retreat
3.0 star property
9.8 out of 10, Exceptional, (22)
"Super easy check in very quite and secluded area great for a romantic get away"
United States
Zachary
Treetop Retreat
Property grounds
Downtown Columbus~Stunning Upscale 1 bd Suite

Apartment in Columbus

Downtown Columbus~Stunning Upscale 1 bd Suite
9.8 out of 10, Exceptional, (6)
"A beautiful property and a great location. Highly recommended!"
United States
bryony
The price is HK$753
HK$1,565 total
includes taxes & fees
6 Jan - 7 Jan 2026
Downtown Columbus~Stunning Upscale 1 bd Suite
Outdoor dining
Betty Lou's Garden Guest Suite

Cottage in Nashville

Betty Lou's Garden Guest Suite
9.6 out of 10, Exceptional, (194)
"Nice place to stay close to all the activities "
United States
Barrett P.
The price is HK$770
HK$1,064 total
includes taxes & fees
11 Jan - 12 Jan 2026
Betty Lou's Garden Guest Suite
Property grounds
Cozy Country Cabin quiet country retreat

Cabin in Orleans

Cozy Country Cabin quiet country retreat
10.0 out of 10, Exceptional, (189)
"We really enjoyed our stay. The cabin is very nice and so is the pond."
United States
Scott H.
The price is HK$875
HK$1,489 total
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Country Cabin quiet country retreat
Property grounds
Walkable Downtown Getaway (FREE Bikes to use)

Holiday Home in Columbus

Walkable Downtown Getaway (FREE Bikes to use)
10.0 out of 10, Exceptional, (3)
"Clean and simple place to stay with great access to downtown Columbus - perfect for enjoying restaurants and architecture tours offered by the town."
United States
Lincoln G.
The price is HK$718
HK$1,193 total
includes taxes & fees
1 Jan - 2 Jan 2026
Walkable Downtown Getaway (FREE Bikes to use)
Outdoor pool
Cozy 2BR Lake Monroe Golf Condo IU Bloomington

Holiday Home in Bloomington

Cozy 2BR Lake Monroe Golf Condo IU Bloomington
10.0 out of 10, Exceptional, (80)
"A nice stay for the one day we was there love the view of the golf course and my grandson saw some deer "
United States
KARLA S.
The price is HK$539
HK$1,431 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy 2BR Lake Monroe Golf Condo IU Bloomington
1 bedroom, desk, WiFi, bed sheets
Peaceful 1-Bedroom Retreat in Town

Holiday Home in Bloomington

Peaceful 1-Bedroom Retreat in Town
2.0 star property
9.6 out of 10, Exceptional, (34)
"Nice stay, well set up, and peaceful. "
United States
William R.
The price is HK$875
HK$1,537 total
includes taxes & fees
1 Jan - 2 Jan 2026
Peaceful 1-Bedroom Retreat in Town
Property grounds
Cozy house on a quiet street

Holiday Home in Bedford

Cozy house on a quiet street
10.0 out of 10, Exceptional, (18)
"Easy access and very clean!"
United States
Jennifer M.
The price is HK$933
HK$2,090 total
includes taxes & fees
12 Jan - 13 Jan 2026
Cozy house on a quiet street
Fridge, microwave, oven, stovetop
Cozy 1-Bedroom Retreat ~ New Remodel, Fast Wi-Fi

Apartment in Columbus

Cozy 1-Bedroom Retreat ~ New Remodel, Fast Wi-Fi
9.8 out of 10, Exceptional, (6)
"I stayed here with my husband and my mother, and we all loved it! The apartment was very modern and clean, and was in a great location. I would definitely recommend staying here, and hope to do so again in the near future!"
United States
Vivian K.
The price is HK$787
HK$1,544 total
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy 1-Bedroom Retreat ~ New Remodel, Fast Wi-Fi
Exterior
Uptown Luxury Studio On The Square Downtown Bloomington

Apartment in Downtown Bloomington

Uptown Luxury Studio On The Square Downtown Bloomington
9.8 out of 10, Exceptional, (20)
"This is the second time I’ve stayed at this Vrbo, and it has been amazing both times! "
United States
Carlos J.
The price is HK$728
HK$1,251 total
includes taxes & fees
1 Jan - 2 Jan 2026
Uptown Luxury Studio On The Square Downtown Bloomington
Fridge, microwave, oven, stovetop
Hoosier Suite Downtown Bloomington On The Square

Apartment in Downtown Bloomington

Hoosier Suite Downtown Bloomington On The Square
9.8 out of 10, Exceptional, (16)
"Very Nice stay. Will stay here again."
United States
Michael L.
The price is HK$728
HK$1,286 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hoosier Suite Downtown Bloomington On The Square
Exterior detail
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

Holiday Home in Hanover

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
9.8 out of 10, Exceptional, (37)
"Great place to stay for Hanover college "
United States
Lindsey M.
The price is HK$903
HK$1,959 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Terrace/patio
A Relaxation Station

Apartment in Morgantown

A Relaxation Station
10.0 out of 10, Exceptional, (97)
"This was our fifth year in a row staying here for vacation. It was very relaxing and stress free. Thanks again for sharing this amazing spot."
United States
Kyle B.
The price is HK$895
HK$2,192 total
includes taxes & fees
8 Jan - 9 Jan 2026
A Relaxation Station
Fireplace
Stunning 4-BR Houses with On-Site Pool

Holiday Home in Bloomington

Stunning 4-BR Houses with On-Site Pool
4.0 star property
8.8 out of 10, Excellent, (3)
"Really nice! "
United States
Jamal
The price is HK$1,718
HK$3,666 total
includes taxes & fees
11 Jan - 12 Jan 2026
Stunning 4-BR Houses with On-Site Pool
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 Jackson County Hotel Reviews

Hilton Garden Inn Bloomington

Hilton Garden Inn Bloomington

10/10 Excellent
"Awesome"
Elijah 2-night trip
Posted 3 days ago
Hilton Garden Inn Bloomington