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Compare 45 Cottages in Crestwood with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (20)
"The property is beautiful. The owners are fantastic. If you love historical buildings that have been restored to capture their history while providing modern comforts, you would be cheating yourself if you didn’t stay at this property. Kudos to the owners!"
2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

2 Mi to Churchill Downs: Louisville Home!

8.8 out of 10, Excellent, (12)
"For our needs the house serves our purpose. "
2 Mi to Churchill Downs: Louisville Home!

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

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

KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

9.8 out of 10, Exceptional, (7)
"Came for a long weekend to do the bourbon trail with friends and stayed at The Blue Belle. House works great for 2 couples, had plenty of room plus having a 3rd bathroom was very nice. Overall very clean and well stocked except for forks but we weren’t home much so it didn’t matter. We were able to walk to nearby restaurants easily. Parking is on the street and the neighborhood is a little odd with a mix of industrial and other cute old houses. Felt safe, but was odd arriving at night and seeing...
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

Beautiful restored Victorian farmhouse

9.2 out of 10, Wonderful, (11)
"Although we had a little hiccup with our check-in, our local owner/hosts Phil and Chris were great hosts for our group of four couples (8 people). Once we connected they made sure everything was ready for our arrival.The house has a lot of rustic charm with many cool and unique furnishings. The full kitchen had everything we needed for preparing our meals in the morning before heading out on the Bourbon Trail and relaxing in the evenings. It is conveniently located close to many of the central...
The price is AED 900
AED 1,753 total
includes taxes & fees
5 May - 6 May
Beautiful restored Victorian farmhouse

Spacious Prospect Cottage w/ Deck & Scenic Views

9.2 out of 10, Wonderful, (16)
"Place just worked for us"
Spacious Prospect Cottage w/ Deck & Scenic Views

Central & Dog-friendly Home in Louisville w/ Yard!

3.0 star property
Central & Dog-friendly Home in Louisville w/ Yard!

Bright New Albany Home: 12 Mi to Churchill Downs!

3.0 star property
Bright New Albany Home: 12 Mi to Churchill Downs!

8 Mi to Louisville: New Albany Home w/ Grill!

3.0 star property
8 Mi to Louisville: New Albany Home w/ Grill!

Shelbyville Home - On to the Bourbon Trail!

3.0 star property
6.0 out of 10, (1)
Shelbyville Home - On to the Bourbon Trail!

Contemporary Cottage with 2 HUGE COVERED PORCHES!

Contemporary Cottage with 2 HUGE COVERED PORCHES!

Indiana Vacation Rental Near Downtown Louisville!

3.0 star property
Indiana Vacation Rental Near Downtown Louisville!

Cozy Home in Louisville: Near Bardstown Road!

3.0 star property
Cozy Home in Louisville: Near Bardstown Road!

Pet-friendly Clarksville Home w/ Central A/C

3.0 star property
Pet-friendly Clarksville Home w/ Central A/C

1 Mi to Downtown: New Albany Home w/ Yard

3.0 star property
1 Mi to Downtown: New Albany Home w/ Yard

Spacious Prospect Cottage w/ Deck & Scenic Views

3.0 star property
Spacious Prospect Cottage w/ Deck & Scenic Views

Walk to Boat Ramp: Fenced Home in Jeffersonville!

3.0 star property
Walk to Boat Ramp: Fenced Home in Jeffersonville!

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

3.0 star property
10.0 out of 10, Exceptional, (1)
"Went for the view of the eclipse with friends. The home was Beautiful! Just as pictures detailed it. Took the fur baby along since it was offered, however left over from last dog droppings in yard and not enclosed yard. The home was perfect for the gathering of friends to mingle and share time/space. The fire pit was a plus factor for the day(chilly) but no fire wood was available without us having to cut our own from a falling tree on property or purchase it. The dishwasher hadn't been...
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

Pet-friendly Emerald Lake Retreat in Charlestown!

3.0 star property
Pet-friendly Emerald Lake Retreat in Charlestown!

Louisville Area Home: Deck, Fire Pit, Creek!

3.0 star property
Louisville Area Home: Deck, Fire Pit, Creek!
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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Other property types in Crestwood

Hancock House

3.0 star property
8.0 out of 10, Very Good, (232)
"Thank you for a good stay "
The price is AED 299
AED 689 total
includes taxes & fees
13 May - 14 May
Hancock House

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (92)
"Outstanding!"
The price is AED 384
AED 638 total
includes taxes & fees
20 May - 21 May
Stellar Suites

The Bellwether Hotel

2.0 star property
8.4 out of 10, Very Good, (13)
"The boutique Bellwether Hotel is so beautiful and a step back in time. The art deco design, the second floor lounge, and the rooms all beautifully decorated and comfortable. Walk to restaurants, grocery, bars and antique shops. "
The price is AED 537
AED 624 total
includes taxes & fees
27 May - 28 May
The Bellwether Hotel
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.