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Featured Cottages in Crestwood

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

3 out of 5
94 Lawson Ln, Shelbyville, KY
Located in Shelbyville, this cottage is within a 15-minute drive of Guist Creek Lake State Park and Weissinger Hills Golf Course.
Opens in a new windowShelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill
Louisville Home w/ Large Yard: 15 Mi to Downtown!

Louisville Home w/ Large Yard: 15 Mi to Downtown!

3 out of 5
Louisville
With a stay at this cottage in Louisville (Highview), you'll be within a 15-minute drive of Kentucky Kingdom and Kentucky Exposition Center.
Opens in a new windowLouisville Home w/ Large Yard: 15 Mi to Downtown!
Cozy Home in Louisville: Near Bardstown Road!

Cozy Home in Louisville: Near Bardstown Road!

3 out of 5
Louisville
With a stay at this cottage in Louisville (Fern Creek), you'll be a 3-minute drive from Outer Loop Plaza Shopping Center and 6 minutes from Piccadilly Square ...
Opens in a new windowCozy Home in Louisville: Near Bardstown Road!
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Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse

Shelbyville
With a stay at this cottage, you'll be centrally located in Shelbyville, within a 15-minute drive of Jeptha Creed Distillery and The Outlet Shoppes of the ...
Opens in a new windowBeautiful restored Victorian farmhouse
Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!

Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!

3 out of 5
New Albany
The price is AU$504 per night from 29 Sept to 30 Sept
AU$504
29 Sept - 30 Sept
includes taxes & fees
With a stay at this cottage in New Albany, you'll be within a 15-minute drive of KFC Yum Center and Whiskey Row.
Opens in a new windowHome w/ Fenced Backyard, 6 Mi to Dtwn Louisville!
2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

Shelbyville
With a stay at this cottage, you'll be centrally located in Shelbyville, within a 15-minute drive of Jeptha Creed Distillery and The Outlet Shoppes of the ...
Opens in a new window2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub
Pet-friendly Clarksville Home w/ Central A/C

Pet-friendly Clarksville Home w/ Central A/C

3 out of 5
Clarksville
With a stay at this cottage in Clarksville, you'll be within a 10-minute drive of KFC Yum Center and Whiskey Row.
Opens in a new windowPet-friendly Clarksville Home w/ Central A/C
Family-friendly Louisville Gem: Prime Location!

Family-friendly Louisville Gem: Prime Location!

3 out of 5
Louisville
With a stay at this cottage in Louisville (Schnitzelburg), you'll be within a 5-minute drive of University of Louisville and Louisville Zoo.
Opens in a new windowFamily-friendly Louisville Gem: Prime Location!
La Grange Cabin on a Racehorse Farm w/ Pond Views!

La Grange Cabin on a Racehorse Farm w/ Pond Views!

3 out of 5
La Grange
Located in La Grange, this cottage is within a 15-minute drive of LaGrange Main Street Visitor Center and La Grange Railroad Museum & Learning Center.
Opens in a new windowLa Grange Cabin on a Racehorse Farm w/ Pond Views!
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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.

Crestwood Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Crestwood will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Crestwood definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Crestwood, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Crestwood Cottages essential information

Accommodation
52 Cottages
Lowest Price
AU$162
Highest Price
AU$504
Popular accommodation
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill, Louisville Home w/ Large Yard: 15 Mi to Downtown!, Cozy Home in Louisville: Near Bardstown Road!, Beautiful restored Victorian farmhouse, Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!, 2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub, Pet-friendly Clarksville Home w/ Central A/C, Family-friendly Louisville Gem: Prime Location!, La Grange Cabin on a Racehorse Farm w/ Pond Views!

Top trending hotels in Crestwood

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is AU$262 per night from 1 Oct to 2 Oct
AU$262
1 Oct - 2 Oct
includes taxes & fees
Galt House Hotel Trademark Collection by Wyndham is in the heart of Louisville, within a 5-minute walk of KFC Yum Center and Kentucky International Convention ...
Opens in a new windowGalt House Hotel Trademark Collection by Wyndham
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is AU$352 per night from 3 Oct to 4 Oct
AU$352
3 Oct - 4 Oct
includes taxes & fees
With a stay at Omni Louisville Hotel, you'll be centrally located in Louisville, steps from Fourth Street Live! and 4 minutes by foot from Kentucky International ...
Opens in a new windowOmni Louisville Hotel
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
830 Phillips Lane, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 29 Sept to 30 Sept
AU$167
29 Sept - 30 Sept
includes taxes & fees
Located in Louisville (Fairgrounds), Crowne Plaza Louisville Airport Expo Ctr by IHG is within a 15-minute walk of Kentucky Kingdom and Kentucky Exposition ...
Opens in a new windowCrowne Plaza Louisville Airport Expo Ctr by IHG
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Express & Suites Louisville Downtown by IHG

Holiday Inn Express & Suites Louisville Downtown by IHG

2.5 out of 5
800 W Market St, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 28 Sept to 29 Sept
AU$162
28 Sept - 29 Sept
includes taxes & fees
A stay at Holiday Inn Express & Suites Louisville Downtown by IHG places you in the heart of Louisville, within a 5-minute walk of Louisville Slugger Museum ...
Opens in a new windowHoliday Inn Express & Suites Louisville Downtown by IHG
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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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^Subject to availability and chosen travel dates.