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Chelsea Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chelsea holiday rentals

A covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and gravel.

1. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
9.4 out of 10, Exceptional, (20 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
United States
MaKayla Q.
The price is HK$565
HK$1,659 total
includes taxes & fees
12 Oct - 13 Oct
Modern cabin very close to scenic riverfront walks
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

2. The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison Historic District
9.6 out of 10, Exceptional, (23 reviews)
"Our room was so cute and perfect for a couple. We loved it! The location was perfect as well!"
United States
Stee
The price is HK$534
HK$987 total
includes taxes & fees
5 Oct - 6 Oct
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Property grounds

3. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (17 reviews)
"Host was very accommodating and this place was perfect for a place to stay while visiting friends. Everything was very comfortable, especially the very soft bed!! "
United States
C J.
The price is HK$699
HK$1,345 total
includes taxes & fees
5 Oct - 6 Oct
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A covered patio with a door, two wicker chairs, and string lights.

4. Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location nice place comfortable "
United States
Hipolito C.
The price is HK$824
HK$1,608 total
includes taxes & fees
24 Oct - 25 Oct
Cozy Tiny House in Scottsburg
A wooden cabin with a porch, a staircase, and a deck.

5. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (16 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is HK$698
HK$1,258 total
includes taxes & fees
2 Nov - 3 Nov
Sassafras Woodland Cabin at Lost Trails
cd294e93-b148-4eb4-b858-151fabf1d0ec

6. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (14 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is HK$785
HK$1,357 total
includes taxes & fees
5 Oct - 6 Oct
Maple Cozy Cabin at Lost Trails
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

7. The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover
9.6 out of 10, Exceptional, (53 reviews)
"Close to downtown Madison and Clifty Falls, this place had everything we needed to visit the area and relax I'm the evening."
United States
Maggie D.
The price is HK$1,024
HK$2,116 total
includes taxes & fees
4 Oct - 5 Oct
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A cozy room with a bed, a chair, a sofa, and a small table.

8. Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Madison Historic District
9.6 out of 10, Exceptional, (8 reviews)
"The host was extremely nice and allowed us to get into the loft a little early. The loft was really nice and we enjoyed out stay. "
United States
Judi K.
The price is HK$798
HK$1,459 total
includes taxes & fees
27 Oct - 28 Oct
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

9. Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is HK$785
HK$1,357 total
includes taxes & fees
5 Oct - 6 Oct
Walnut Secluded Cabin at Lost Trails
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

10. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"This is a total hidden gem! The cabin seemed brand new and was outfitted with everything you might need. We spent our 25th wedding anniversary weekend here and loved every second! Would highly recommend!"
United States
Jodi E.
The price is HK$785
HK$1,357 total
includes taxes & fees
5 Oct - 6 Oct
Mulberry Secluded Cabin at Lost Trails
A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

11. Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (25 reviews)
"Amazing, would stay again in a heartbeat"
United States
Ian M.
The price is HK$840
HK$1,259 total
includes taxes & fees
5 Oct - 6 Oct
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A covered porch with a wooden door, potted plants, and a metal railing.

12. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (41 reviews)
"Very nice house and convenient to downtown, etc. If you stay here you definitely won’t be disappointed."
United States
Shirley L.
The price is HK$1,075
HK$2,025 total
includes taxes & fees
25 Oct - 26 Oct
The Artist’s A-Frame
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

13. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (31 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is HK$863
HK$1,448 total
includes taxes & fees
6 Oct - 7 Oct
Cedar Rustic Cabin at Lost Trails
A house with a large garage, a dock, and a river.

14. River Retreat

River Retreat
Charlestown
10.0 out of 10, Exceptional, (1 review)
"Easy check in. Nice cozy home right by the river. Even left a golf cart for use when staying!"
United States
Brady S.
The price is HK$973
HK$2,261 total
includes taxes & fees
5 Oct - 6 Oct
River Retreat
Room

15. Country living minutes away from Churchill Downs, Airport, major attractions.

Country living minutes away from Churchill Downs, Airport, major attractions.
Charlestown
9.6 out of 10, Exceptional, (7 reviews)
"So glad we went here for our mini getaway! Definitely a unique place to stay. Room was great and we got to tour other areas in and around the castle. David is a great host and we enjoyed talking with him! Going to try and make it back up for the festival this fall."
United States
Cari H.
The price is HK$981
HK$1,507 total
includes taxes & fees
28 Oct - 29 Oct
Country living minutes away from Churchill Downs, Airport, major attractions.
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

16. The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Madison Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is HK$485
HK$935 total
includes taxes & fees
18 Oct - 19 Oct
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

17. The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Madison Historic District
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our visit and would recommend to others looking for a convenient location and comfortable stay."
United States
Renee M.
The price is HK$471
HK$887 total
includes taxes & fees
13 Oct - 14 Oct
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

18. Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (76 reviews)
"Love the stay very relaxed"
United States
Steve C.
The price is HK$883
HK$1,827 total
includes taxes & fees
4 Oct - 5 Oct
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

19. The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205

The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205
Madison Historic District
9.8 out of 10, Exceptional, (7 reviews)
"Cozy, peaceful, wonderful with great location. "
United Kingdom
Ed E.
The price is HK$494
HK$945 total
includes taxes & fees
26 Oct - 27 Oct
The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205
A room with a bed, two armchairs, a small table, and a microwave.

20. Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
Henryville
10.0 out of 10, Exceptional, (1 review)
"Awesome place in a gated property. The tiny home is exactly as pictured. Will 100% stay here again for future Henryville visits to see family."
United States
Jonathan B.
The price is HK$1,053
HK$2,416 total
includes taxes & fees
5 Oct - 6 Oct
Lakeside Cottage: 1 bed/1 bath
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 Chelsea Hotel Reviews

HavenPointe Inn & Suites

HavenPointe Inn & Suites

10/10 Excellent
"The shower could use handrails as the floor seemed slick. We put a towel down on the shower floor and everything was fine."
John 1-night trip
Posted 17 hours ago
HavenPointe Inn & Suites

Find out more about Chelsea

Search for holiday rentals in Chelsea on Expedia! You can easily find your home rentals, villas, holiday apartments in Chelsea using one of the methods below:

  • View our selection of featured holiday rentals in Chelsea
  • Use the map to find apartments and other holiday homes in the Chelsea neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chelsea while they last

Look no further and take a look at our great range of rental properties in Chelsea!

Frequently asked questions

Can I find a holiday rental in Chelsea?

Yes, there are holiday rentals close to the most popular sights in Chelsea, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chelsea has to offer?

Red comfy cottage : This holiday home rental outside of Chelsea offers an indoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Chelsea?

Explore the area and family-friendly sights such as Madison Railroad Station Museum, or get out into nature at a spot like Hardy Lake. In the wider area, you’ll find Clifty Falls State Park and Lanthier Winery.

What’s a holiday rental in Chelsea like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chelsea. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.