Photo by Christ Medina

Search Cottages in Crestwood

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

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

2 Mi to Churchill Downs: Louisville Home!

8.8 out of 10, Excellent, (11)
"The location and residence met the needs of 4 adults. "
2 Mi to Churchill Downs: Louisville Home!

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 didnā€™t stay at this property. Kudos to the owners!"
2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

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 werenā€™t home much so it didnā€™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, (10)
"Phil was great at communicating and responding. The Victorian home was as described. You got the modern conveniences with the Victorian vibe all in one. Clean and plenty of amenities and extra blankets which I was grateful for. While it was secluded in the back, I would have liked blinds or shutters on the big bay windows for privacy where the kids were on the sleeper sofa. Otherwise itā€™s was perfect!"
The price is AEDĀ 900
AEDĀ 1,744 total
includes taxes & fees
12 Mar - 13 Mar
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!

1 Mi to Downtown: New Albany Home w/ Yard

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

Pet-friendly Clarksville Home w/ Central A/C

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

Contemporary Cottage with 2 HUGE COVERED PORCHES!

Contemporary Cottage with 2 HUGE COVERED PORCHES!

Shelbyville Home - On to the Bourbon Trail!

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

Walk to Boat Ramp: Fenced Home in Jeffersonville!

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

Cozy Home in Louisville: Near Bardstown Road!

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

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

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

Spacious Prospect Cottage w/ Deck & Scenic Views

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

Indiana Vacation Rental Near Downtown Louisville!

3.0 star property
Indiana Vacation Rental Near Downtown Louisville!

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

Louisville Area Home: Deck, Fire Pit, Creek!

3.0 star property
Louisville Area Home: Deck, Fire Pit, Creek!

Pet-friendly Emerald Lake Retreat in Charlestown!

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

7 Mi to Louisville: Pet-friendly New Albany Home

3.0 star property
7 Mi to Louisville: Pet-friendly New Albany Home
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.
Don't see what you're looking for?
See all available properties in Crestwood
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Crestwood

Hancock House

3.0 star property
8.0 out of 10, Very Good, (217)
"Favorite place to stay in Louisville "
The price is AEDĀ 322
AEDĀ 587 total
includes taxes & fees
12 Mar - 13 Mar
Hancock House

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (91)
"Outstanding!"
The price is AEDĀ 448
AEDĀ 711 total
includes taxes & fees
30 Mar - 31 Mar
Stellar Suites

The Bellwether Hotel

2.0 star property
8.0 out of 10, Very Good, (11)
"Beautifully redone historic building. Enjoyed design features and Christmas decor! Great walkable neighborhood. "
The price is AEDĀ 561
AEDĀ 651 total
includes taxes & fees
16 Mar - 17 Mar
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.

Frequently asked questions

Why book your cottage in Crestwood with Expedia?
Reserving a cottage in Crestwood is as easy as working out your travel dates and selecting an ideal place for a vacation in nature. From upscale retreats to inexpensive properties and cottages that have perks like a hot tub, Expedia has something for all styles and tastes. As for epic deals? Weā€™ve got them too!
How can I find cheap cottages in Crestwood?
With Expediaā€™s user-friendly filter tool, scoring cheap cottages in Crestwood is easy. To find stays thatā€™ll make your wallet smile, refine your search by amenities, star rating and budget.