Holiday Rentals in Chelsea

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Our top choices for Chelsea holiday rentals

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Pendleton
9.8 out of 10, Exceptional, (62)
"Came to the area for a funeral. Worked out great for our needs. Alecia was quick to respond any time we called. Enjoyed it. "
United Kingdom
Clyde C.
The price is €201
includes taxes & fees
20 Dec - 21 Dec
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

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

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
2.0 star property
Madison
The price is €140
includes taxes & fees
18 Dec - 19 Dec
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
The price is €196
includes taxes & fees
4 Jan - 5 Jan 2026
The Artist’s A-Frame

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
2.0 star property
Madison
10.0 out of 10, Exceptional, (15)
"Great little place. Location was exceptional. "
United States
Andrew P.
The price is €108
includes taxes & fees
18 Dec - 19 Dec
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Modern Nature Cabin | Private Escape in the Forest

Modern Nature Cabin | Private Escape in the Forest
Hanover
9.8 out of 10, Exceptional, (7)
"Very nice facility and relaxing setting . "
United States
Robert V.
The price is €162
includes taxes & fees
4 Jan - 5 Jan 2026
Modern Nature Cabin | Private Escape in the Forest

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, (12)
"The property was clean and quiet. Great location in a nice residential neighborhood. Very close to Charlestown State Park where we did some hiking."
United States
Chris S.
The price is €129
includes taxes & fees
18 Dec - 19 Dec
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is €186
includes taxes & fees
18 Dec - 19 Dec
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown
Charlestown
10.0 out of 10, Exceptional, (3)
"This a great place for families to gather. It's very spacious and clean and comfortable. And though it's in a quiet and peaceful area with a small lake at the base of the property, places to eat and get groceries are just a short drive away. There's a wonderful seating area around a firepit, too!"
United States
Kelly P.
Emerald Lake Retreat Charlestown

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
9.8 out of 10, Exceptional, (10)
"Super comfortable, clean little apartment in a quiet area off the main strip. We loved out stay!"
United States
Courtney G.
The price is €124
includes taxes & fees
4 Jan - 5 Jan 2026
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

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
9.8 out of 10, Exceptional, (34)
"Great place to stay for Hanover college "
United States
Lindsey M.
The price is €220
includes taxes & fees
28 Dec - 29 Dec
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

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

Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (4)
"Wonderful accommodations. Comfortable and clean. We enjoyed our stay. I am sure we will return as Hope was a great host."
United States
Karen P.
The price is €151
includes taxes & fees
29 Dec - 30 Dec
Cozy Tiny House in Scottsburg

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Madison
9.6 out of 10, Exceptional, (20)
"My wife and I enjoyed our stay here while checking out Madison. Great location, nicely decorated. "
United States
Justin L.
The price is €252
includes taxes & fees
18 Dec - 19 Dec
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Sleeps 4, Rustic, Secluded

Sleeps 4, Rustic, Secluded
Lexington
8.0 out of 10, Very good, (4)
"The cabin and property were very clean and easy to find. We loved the back yard for chilling around after we got back from the event we were attending. Host was very friendly and had good communication. Will stay again if we are back in the area! "
United States
Nicole C.
The price is €190
includes taxes & fees
18 Dec - 19 Dec
Sleeps 4, Rustic, Secluded

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, (53)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
The price is €216
includes taxes & fees
18 Dec - 19 Dec
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
2.0 star property
Madison
The price is €366
includes taxes & fees
30 Dec - 31 Dec
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home
2.0 star property
La Grange
10.0 out of 10, Exceptional, (5)
"We had a family gathering over Thanksgiving and the large table was very nice and appreciated. Host was very prompt with communication and most everything we needed was there. Would stay again!"
United States
Shelley S.
The price is €312
includes taxes & fees
17 Jan - 18 Jan 2026
The Sweet Retreat Wheelchair Accessible Historic Home

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Madison
10.0 out of 10, Exceptional, (14)
"Madison Manor II was perfect for our annual girls trip. We were comfortable, location was great, the home was very clean."
United States
Carissa N.
The price is €314
includes taxes & fees
18 Dec - 19 Dec
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Hanover
9.2 out of 10, Wonderful, (5)
"It was lovely!"
United States
Carolyne R.
The price is €433
includes taxes & fees
17 Jan - 18 Jan 2026
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

Country home with beautiful views and access to hiking, biking, and horse trails

Country home with beautiful views and access to hiking, biking, and horse trails
Henryville
10.0 out of 10, Exceptional, (30)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is €219
includes taxes & fees
20 Dec - 21 Dec
Country home with beautiful views and access to hiking, biking, and horse trails
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

Find out more about Chelsea

Everything you need to know about Chelsea holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chelsea holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chelsea holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chelsea holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chelsea. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chelsea holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chelsea holiday rentals we have selected for you start as low as €108 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chelsea rentals

At Expedia, we put the best Chelsea holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chelsea rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chelsea holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chelsea. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: This holiday home rental outside of Chelsea offers a patio, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.