Chelsea Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
20 Jul - 21 Jul
Tomorrow
21 Jul - 22 Jul
Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug

Holiday Rentals in Chelsea

1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Enjoy serene lakeside views from the porch of this charming lakeside retreat, where you can relax and unwind amidst lush greenery.

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

10.0 out of 10, Exceptional, (190)
"Great getaway. View is fantastic!!! Location with plenty of privacy!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Modern kitchen with stainless steel appliances, light grey cabinetry, and a black and white patterned rug.

River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

10.0 out of 10, Exceptional, (4)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Enjoy cooking and socializing in this kitchen with a central island and bar stools, featuring stainless steel appliances and a pendant light fixture.

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

9.8 out of 10, Exceptional, (30)
"Clean, comfortable home with everything needed for our stay. "
The price is NZ$417
includes taxes & fees
3 Aug - 4 Aug
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Stoney Creek - Sit back and unwind
Enjoy cooking in this inviting kitchen with a central island, oven, and window overlooking the surrounding landscape.

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (89)
"Perfect setting. Beautiful cabin. "
Stoney Creek - Sit back and unwind
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Compact kitchen with modern design, featuring an oven, microwave, and window.

The Wee House is a shotgun house that is remodeled with a view of the Ohio river

9.6 out of 10, Exceptional, (49)
"We loved the Wee House. It was great at the end of the day to sit on the porch, listen to the birds, and watch the barges on the river. The kitchen had everything we needed. We especially liked the quilts on the beds--so cheerful and colorful. And the location was perfect--just two short blocks from Main Street so we could walk everywhere."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Rustic cabin just outside of Madison!
Relax in a spacious room with a four-poster bed, wooden headboard, and a ceiling fan.

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (39)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
Rustic cabin just outside of Madison!
Rustic Cabin at Lost Trails
Guests can enjoy a secluded retreat in this cabin, surrounded by mature trees and featuring a spacious porch with a railing.

Rustic Cabin at Lost Trails

10.0 out of 10, Exceptional, (5)
"It was a great peaceful getaway for my wife and I. Quiet and clean. "
Rustic Cabin at Lost Trails
Historic woodside view suite 205, Historic woodside view suite 205
Compact kitchen with a black stove, stainless steel oven, microwave, and white cabinetry.

Historic woodside view suite 205, Historic woodside view suite 205

9.6 out of 10, Exceptional, (4)
"We had a wonderful experience during our stay. The property was exactly as described clean, cozy, and comfortable. The neighborhood was quiet, and check-in was seamless. Would definitely recommend this place to anyone looking for a relaxing, hassle-free stay!"
The price is NZ$267
includes taxes & fees
13 Aug - 14 Aug
Historic woodside view suite 205, Historic woodside view suite 205
Relaxing Country Getaway
Cozy space with a fireplace, leather sofa, and wooden panel walls, perfect for relaxing.

Relaxing Country Getaway

9.4 out of 10, Exceptional, (33)
"Wonderful stay, very private. Cozy place perfect for couples looking to unwind. Would stay again."
Relaxing Country Getaway
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Relax in a comfortable living space with a sectional sofa and large mirror.

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

10.0 out of 10, Exceptional, (43)
"This is the second time staying at this unit. Next weekend, we are going down and staying in the upstairs loft. Looking forward. Always a great time staying with Suzie. Highly recommend."
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Set within a brick wall, this charming entrance features a decorative wreath and a welcoming doormat.

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

10.0 out of 10, Exceptional, (24)
"The place was very cute, clean, and comfortable. Great stay! Host was very responsive. "
The price is NZ$421
includes taxes & fees
28 July - 29 July
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Cozy cabin features a dining area, seating area, and living room with a fireplace and TV.

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

10.0 out of 10, Exceptional, (146)
"Our family had a spectacular stay at the Stone Creek. Our kids (7, 3, 2 yo) had a blast playing pingpong, board games, and hot tub. Place was clean and we felt home. We’ll definitely come back!"
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
East End River Retreat: Dogs Welcome!
Enjoy cooking and dining in this classic kitchen with a central island, sink, and countertop, connected to a dining area with a table and chairs.

East End River Retreat: Dogs Welcome!

10.0 out of 10, Exceptional, (5)
"We had a lovely time. Great property with easy access to everything. Our kids loved the golf cart and we appreciated the extra touches from the owners. Great little house for a stay in a great little town."
East End River Retreat: Dogs Welcome!
The Wadsworth in National Historic District of Madison, Indiana.
Enjoy cooking in this well-equipped kitchen with an oven and stovetop.

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (50)
"We absolutely loved our stay in Madison at the Wadsworth House! You couldn't ask for a nicer place to stay for a quiet get away!"
The Wadsworth in National Historic District of Madison, Indiana.
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Fully equipped kitchen with microwave, stove, sink, and refrigerator.

Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

10.0 out of 10, Exceptional, (4)
"Riverside Retreat is a must stay! It is a great location and exactly as described. Highly recommend. We will be back!"
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Emerald Lake Retreat Charlestown
Property grounds

Emerald Lake Retreat Charlestown

10.0 out of 10, Exceptional, (1)
"Excellent communication, fast responses, very accommodating. The layout is fantastic with lots of open space, comfortable bedrooms, and excellent amenities. The backyard is absolutely huge, probably 3 acres or so. Would stay again for sure."
The price is NZ$752
includes taxes & fees
22 July - 23 July
Emerald Lake Retreat Charlestown
The Artist’s A-Frame
Enjoy a view of the surrounding greenery from the large window.

The Artist’s A-Frame

10.0 out of 10, Exceptional, (12)
"Stayed for the weekend to hike at Clifty Falls. Great location to the state park and downtown restaurants. Really pretty house with everything you’d need for a stay. Host was super nice to interact with as well. Thanks again! "
The price is NZ$388
includes taxes & fees
23 July - 24 July
The Artist’s A-Frame
Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
Relax by the fire pit in a serene backyard setting with a seating area and pathway.

Beautiful and spacious 3BR historic home centrally located in downtown, Madison.

10.0 out of 10, Exceptional, (44)
"We had a great stay and the communication was terrific. Thanks SW"
Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!
Enjoy al fresco dining on the patio with a grill and scenic views.

The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!

10.0 out of 10, Exceptional, (42)
"Prefect accommodations for a weekend getaway. A beautiful space, friendly owners, and a private setting."
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!
Bungalow on Main!!
Traditional home with a symmetrical facade, featuring a decorative front door and a small porch area.

Bungalow on Main!!

9.8 out of 10, Exceptional, (12)
"This place was great. The wife and I need a little getaway to relax and recharge. Our stay here was perfect for that. Nice amenities and the private hottub was really relaxing. Will definitely book here again. "
Bungalow on Main!!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chelsea Hotel Reviews

Riverboat Inn and Suites

Riverboat Inn and Suites

10/10 Excellent
"Smallish room, but clean and nice for a night."
Matthew 1-night trip
Posted 2 days ago
Riverboat Inn and Suites

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 Linza Graham Park. 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.