Chelsea Holiday Rentals

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Holiday Rentals in Chelsea

Sunset over the city Suite 201, Sunset over the city Suite 201

Madison
9.8 out of 10, Exceptional, (12)
"We have watched the Riverside Inn being restored, and couldn't be happier to finally stay there. We only gave overall a 4star because the door was very difficult to lock. It kept popping the latch. No biggie as we didn't feel unsafe."
United Kingdom
Janene H.
The price is NZ$230
includes taxes & fees
18 Nov - 19 Nov
Sunset over the city Suite 201, Sunset over the city Suite 201

Rustic cabin just outside of Madison!

Madison
10.0 out of 10, Exceptional, (49)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
United States
Michelle S.
Rustic cabin just outside of Madison!

Stoney Creek - Sit back and unwind

Madison
10.0 out of 10, Exceptional, (101)
"It’s was amazing! The listing was completely accurate! Communication was a breeze!"
United States
Bobbie R.
Stoney Creek - Sit back and unwind

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

Madison
9.8 out of 10, Exceptional, (47)
"We were able to check in early. The house is very cute and we enjoyed using the golf cart to explore around town. We enjoyed hanging out in the evening in the house. It had everything we needed and it was very clean. We would definitely stay there again,"
United States
Karen W.
The price is NZ$396
includes taxes & fees
17 Nov - 18 Nov
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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

Madison
10.0 out of 10, Exceptional, (60)
"Great property, great location, and amazing hosts. Incredible attention to detail and service. It would take too long to describe everything that impressed us so I'll just say it's all perfect and if this place is available when you're visiting Madison, stop searching and just book it."
United States
John S.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

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

Pendleton
9.8 out of 10, Exceptional, (59)
"My husband and I enjoyed this sweet country retreat. The peaceful setting encouraged much relaxation and long conversations. Perfect weekend."
United States
Rita G.
The price is NZ$407
includes taxes & fees
16 Nov - 17 Nov
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Madison
9.8 out of 10, Exceptional, (10)
"Nice new property in a great location!"
United States
John B.
The price is NZ$214
includes taxes & fees
9 Dec - 10 Dec
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Sleeps 4, Rustic, Secluded

Lexington
8.0 out of 10, Very good, (3)
"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 NZ$409
includes taxes & fees
17 Nov - 18 Nov
Sleeps 4, Rustic, Secluded

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

Henryville
10.0 out of 10, Exceptional, (153)
"Peaceful, beautiful place. Very homey and excellent outdoor firepit. Did not like the downstairs shower. All other aspects were great and the artistic detail was excellent."
United States
Mary Nugent T.
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Cozy Tiny House in Scottsburg

Scottsburg
9.0 out of 10, Wonderful, (2)
"Host was nice. The tiny house was cute and very clean. I wish there had been a blanket for the sofa bed and a toaster. But there was a Dollar General just down the street. All in all is was a sweet little place to stay."
United States
Thomas C.
The price is NZ$311
includes taxes & fees
11 Dec - 12 Dec
Cozy Tiny House in Scottsburg

Cozy Cabin Madison Indiana

Milton
10.0 out of 10, Exceptional, (18)
"Cabin was relatively secluded, in a pretty location and exactly as described. 5 minutes from downtown Madison Indiana which is a beautiful old river town. Host was exceedingly accommodating and gracious and the property has everything you need. Will definitely book again. "
United States
Clay G.
Cozy Cabin Madison Indiana

Red comfy cottage

Madison
10.0 out of 10, Exceptional, (80)
"House was clean and close to town"
United States
Sharon N.
Red comfy cottage

The Wadsworth in National Historic District of Madison, Indiana.

Madison
10.0 out of 10, Exceptional, (62)
"Decorating was very nice. Loved the back patio. The whole experience was just perfect. I highly recommend this property. "
United States
Patricia H.
The Wadsworth in National Historic District of Madison, Indiana.

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Madison
9.6 out of 10, Exceptional, (19)
"Very clean and cozy"
United States
Susie I.
The price is NZ$512
includes taxes & fees
21 Nov - 22 Nov
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

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

Madison
10.0 out of 10, Exceptional, (208)
"Francine's Cabin is such a peaceful and private place to stay. We love it and have stayed there several times. "
United States
Tammy C.
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

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

Madison
10.0 out of 10, Exceptional, (19)
"Great one bedroom apartment! It was clean and great location for our quick getaway."
United States
Eric S.
The price is NZ$378
includes taxes & fees
16 Nov - 17 Nov
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Madison
9.4 out of 10, Exceptional, (23)
"Very nice house good accommodations would stay again !!!"
United States
Henry C.
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

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

Charlestown
10.0 out of 10, Exceptional, (11)
"We enjoyed the spacious rooms, quick access to local restaurants and how well equipped the space was. Our host Tiffinie was super responsive and helpful. The entry stairs were a little challenging after a full day of exploring but manageable. The apartment was located on a historical block with cool old houses Next-door. Overall a really terrific stay!"
United States
Shelly D.
The price is NZ$259
includes taxes & fees
24 Nov - 25 Nov
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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

2.0 star property
Madison
10.0 out of 10, Exceptional, (12)
"Location, location, location! A great spot if you want to walk around Madison! Close to the river, restaurants, bars, trolley. Our only issue was the room was too warm for sleeping and no controls to change. Bed was good, cute little coffees, parking was good. We didn’t move outlets car at all, we walked everywhere."
United States
Tina H.
The price is NZ$297
includes taxes & fees
24 Nov - 25 Nov
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

Madison
8.8 out of 10, Excellent, (10)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is NZ$245
includes taxes & fees
18 Nov - 19 Nov
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
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, 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 NZ$214 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 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.