Chelsea Holiday Rentals

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Check prices for these dates

Tonight
20 Feb - 21 Feb
Tomorrow
21 Feb - 22 Feb
This weekend
21 Feb - 23 Feb
Next weekend
28 Feb - 2 Mar

Holiday Rentals in Chelsea

1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Property grounds

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

10.0 out of 10, Exceptional, (180)
"Beautiful, stunning views!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Interior

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

10.0 out of 10, Exceptional, (23)
"This place is awesome! It’s the best place to stay in Madison, IN. Well decorated and has everything you need. The host Suzie goes over and above to make sure your stay is memorable. Great location in town. We already have future dates reserved and will add more in 2025. "
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Stoney Creek - Sit back and unwind
Terrace/patio

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (70)
"Was a beautiful cabin wonderful hot tub awesome views loved the cows "
The price is AU$358
includes taxes & fees
23 Feb - 24 Feb
Stoney Creek - Sit back and unwind
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River
Exterior

Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

9.8 out of 10, Exceptional, (39)
"The space was perfect for 4 of us traveling for a girls’ trip. Location was close to all the shops and restaurants. "
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River
Family/Pet-Friendly Riverside Home w/Amazing Views
Terrace/patio

Family/Pet-Friendly Riverside Home w/Amazing Views

9.2 out of 10, Wonderful, (19)
"This was our second stay at the River house. We had a great stay!! I Love the view from the deck!! "
Family/Pet-Friendly Riverside Home w/Amazing Views
Close to Louisville ,Hot Tub, Fire Pit, Game Room, and 4 Bedrooms 3 Baths
Smart TV, fireplace, video games, DVD player

Close to Louisville ,Hot Tub, Fire Pit, Game Room, and 4 Bedrooms 3 Baths

10.0 out of 10, Exceptional, (136)
"We loved having a long weekend in this wonderful cabin. Has everything you need, we really enjoyed the hot tub and having plenty of room to spread out and veg and play games. Ample kitchen with everything we needed. "
Close to Louisville ,Hot Tub, Fire Pit, Game Room, and 4 Bedrooms 3 Baths
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (22)
"Had a good time "
The price is AU$358
includes taxes & fees
23 Feb - 24 Feb
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
Exterior

The Waterfall Suite Place + Walkout! Both Overlook Waterfall!

9.8 out of 10, Exceptional, (40)
"We were hit with a snowstorm the day we were to arrive. Our crew all lives within a few hours but roads got pretty bad pretty quickly and we all arrived much later than expected, and even with 4 wheel drive none of us were able to get our cars up the driveway. The owners were kind enough to shuttle us (all 13 of us!) and our belongings up to the house in their big beast of a truck as we all arrived throughout the evening. Very much appreciated! It was a wonderful stay and we all had a great...
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
Restaurant

Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

10.0 out of 10, Exceptional, (42)
"The house is stunning. Very well decorated and completely outfitted for our stay. The kitchen had everything you could need. The owners were easy to communicate with and very helpful. Would highly recommended the property. "
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
Rustic cabin just outside of Madison!
4 bedrooms, free WiFi, bed sheets

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (32)
"This cabin was off the beaten path and nestled in the woods. Very nice cabin with all the amenities you could ask for. Definitely needed a 4x4 vehicle crossing the stream. It was still full of ice and snow from the recent storm. Will stay again when in the area. "
Rustic cabin just outside of Madison!
Livery Loft: our other BEST downtown location! Award winning! Come see why.
Aerial view

Livery Loft: our other BEST downtown location! Award winning! Come see why.

10.0 out of 10, Exceptional, (11)
"This place. This owner. This was far beyond our expectations ! The location is beautiful. Comfortable . Spotless. Safe. There is no stone left unturned in this property. The owner, Suzie, is absolutely lovely. She makes the stay so comfortable and makes sure that you know where everything is . The town is fantastic and we had the time of our lives. Already looking forward for our next trip ! Thank you !!"
Livery Loft: our other BEST downtown location! Award winning! Come see why.
Hardy lake house. Ideal for relax fishing and spending quality time on lake.
Property grounds

Hardy lake house. Ideal for relax fishing and spending quality time on lake.

2.0 star property
9.8 out of 10, Exceptional, (9)
"Cute clean and well stocked. Was a perfect place to spend an early thanksgiving with grandkids"
Hardy lake house. Ideal for relax fishing and spending quality time on lake.
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (13)
"Nice quiet neighborhood, comfortable place to be to unwind after each day of visiting my home town, family and friends. Property manager was very helpful. I will certainly consider for future trips to this area."
The price is AU$424
includes taxes & fees
23 Feb - 24 Feb
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
#207 King Suites, River Views, Deck, Downtown
Interior

#207 King Suites, River Views, Deck, Downtown

10.0 out of 10, Exceptional, (29)
"We had a 5 couples get away for one evening and stayed in the house. A great view of the river and perfect location for walks to the shops, Park and restaurants. We plan on staying here again in the future! "
The price is AU$843
includes taxes & fees
23 Feb - 24 Feb
#207 King Suites, River Views, Deck, Downtown
Bungalow on Main!!
Exterior

Bungalow on Main!!

9.6 out of 10, Exceptional, (7)
"Place was clean, downtown, and what pictures shown. Owner was kind and understanding. "
Bungalow on Main!!
#209 Kings, River View, Deck, Bicentennial Park
Fridge, microwave, oven, stovetop

#209 Kings, River View, Deck, Bicentennial Park

10.0 out of 10, Exceptional, (55)
"Nice property and well equipped. We had no problem cooking full breakfast and full dinner for 8 people. Nice location for walking to places in town."
The price is AU$843
includes taxes & fees
23 Feb - 24 Feb
#209 Kings, River View, Deck, Bicentennial Park
THE WATERFALL WALKOUT & HILLTOP RETREAT, SLEEPS 10+, 4BR*2BA
Property grounds

THE WATERFALL WALKOUT & HILLTOP RETREAT, SLEEPS 10+, 4BR*2BA

9.8 out of 10, Exceptional, (45)
"We had a wonderful family Christmas in January with 8 adults and 3 little ones. Loved the open floor plan and all of the glass overlooking the waterfalls and woods. Electric fireplace is inviting and even puts out heat! Our hosts generously left the Christmas tree and decorations up for our family. Our crew loved the hot tub (quite large), the oven that goes to 550 (for pizza), the large bowls and utensils for cooking, and the beautiful scenery for walks, play, and photos. "
THE WATERFALL WALKOUT & HILLTOP RETREAT, SLEEPS 10+, 4BR*2BA
The Artist’s A-Frame
Exterior

The Artist’s A-Frame

10.0 out of 10, Exceptional, (10)
"We were a group of three longtime friends in town for a holiday weekend together. The Artist’s A-Frame was the perfect place to retire at the end of a great day of shopping and eating. The home was clean, cozy, and well-appointed, and it was located in a lovely neighborhood. The owners were very responsive and easy to work with. Highly recommend the A-Frane! "
The price is AU$373
includes taxes & fees
2 Mar - 3 Mar
The Artist’s A-Frame
Private Retreat:Saltwater Pool, Hot Tub & Fire Pit
Exterior detail

Private Retreat:Saltwater Pool, Hot Tub & Fire Pit

10.0 out of 10, Exceptional, (11)
"This place was amazing it had everything you could ever need fully equipped kitchen with spices, coffee,all small appliances even a basket of snacks,beach towels for hot tub,all kind of games,even bath bombs,the most relaxing front porch with rocking chairs,all of our grandkids absolutely loved it and wished we could have stayed longer. The hosts were amazing in every way and was there if we need anything. This home was so fun we never left our whole stay."
Private Retreat:Saltwater Pool, Hot Tub & Fire Pit
Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!
Fridge, microwave, oven, stovetop

Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!

10.0 out of 10, Exceptional, (24)
"This was a wonderful place for our weekend in Madison. We walked everywhere we wanted to go. The house is very clean and updated with everything we needed. We really appreciated having large beds and bathrooms for each bedroom. "
Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!
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 types of properties in Chelsea you may be interested in

Hillside Inn
Property amenity

Hillside Inn

2.5 star property
8.6 out of 10, Excellent, (985)
"It fit our needs for the night. "
The price is AU$114
includes taxes & fees
25 Feb - 26 Feb
Hillside Inn
Best Way Inn Madison
Indoor pool, pool loungers

Best Way Inn Madison

2.5 star property
6.8 out of 10, (466)
"I like the quietness around the grounds."
The price is AU$100
includes taxes & fees
27 Feb - 28 Feb
Best Way Inn Madison
Holiday Inn Express & Suites Scottsburg by IHG
Property amenity

Holiday Inn Express & Suites Scottsburg by IHG

2.5 star property
8.6 out of 10, Excellent, (566)
"Oig"
The price is AU$160
includes taxes & fees
23 Feb - 24 Feb
Holiday Inn Express & Suites Scottsburg by IHG
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

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 Clifty Falls State Park. In the wider area, you’ll find Lanthier Winery and Lanier Mansion.

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.