Chelsea Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Chelsea

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

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 AU$202
includes taxes & fees
18 Nov - 19 Nov
Sunset over the city Suite 201, Sunset over the city Suite 201
Fridge, microwave, oven, stovetop
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, (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 AU$356
includes taxes & fees
16 Nov - 17 Nov
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Terrace/patio
Pendleton, KY Farm in Oldham Co

Pendleton, KY Farm in Oldham Co

Pendleton
10.0 out of 10, Exceptional, (4)
"The house was perfect for our group of 8. Very clean, great gathering space inside and out and well maintained. Highly recommended! Thanks Betty!"
United States
Scott B.
The price is AU$1,460
includes taxes & fees
15 Nov - 16 Nov
Pendleton, KY Farm in Oldham Co
Fridge, microwave, oven, stovetop
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, (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 AU$347
includes taxes & fees
17 Nov - 18 Nov
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Fridge, microwave, oven, stovetop
Modern Nature Cabin | Private Escape in the Forest

Modern Nature Cabin | Private Escape in the Forest

Hanover
9.8 out of 10, Exceptional, (7)
"Everything was super comfortable and clean the owner was super friendly helpful and quick to respond to any questions I had and was available 24-7 I look forward to staying there again "
United States
Adam J.
The price is AU$290
includes taxes & fees
17 Nov - 18 Nov
Modern Nature Cabin | Private Escape in the Forest
Exterior
Cozy Tiny House in Scottsburg

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 AU$277
includes taxes & fees
15 Nov - 16 Nov
Cozy Tiny House in Scottsburg
Interior
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, (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 AU$228
includes taxes & fees
24 Nov - 25 Nov
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Exterior
The Artist’s A-Frame

The Artist’s A-Frame

Madison
10.0 out of 10, Exceptional, (24)
"Great location, quiet neighborhood. Hosts thought of everything we might need. Home was well appointed and beds were very comfortable. "
United States
Anonymous traveller
The price is AU$379
includes taxes & fees
14 Dec - 15 Dec
The Artist’s A-Frame
Exterior detail
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, (33)
"The property was great! Excellent location with great proximity to Madison and Clifty Falls! Very clean and accommodating to dogs! Love the pet friendly aspect! Was a large decider in choosing this lovely house! Would gladly choose it again when in the area!"
United States
Eric C.
The price is AU$390
includes taxes & fees
23 Nov - 24 Nov
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Exterior
Sleeps 4, Rustic, Secluded

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 AU$359
includes taxes & fees
17 Nov - 18 Nov
Sleeps 4, Rustic, Secluded
Fridge, microwave, oven, stovetop
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, (19)
"Very clean and cozy"
United States
Susie I.
The price is AU$448
includes taxes & fees
14 Nov - 15 Nov
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Microwave, oven, stovetop, dishwasher
Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront

Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront

Madison
10.0 out of 10, Exceptional, (1)
"Our stay at this beautiful old home on Main Street in Madison was fantastic. The property has been beautifully maintained and modernized just enough to be comfortable without losing the gorgeous, authentic feel of an old home that clearly has stories to tell.The rooms were spacious and incredibly comfortable, providing plenty of room to relax. The location simply can't be beat—we loved that we could easily walk to all the local shops and great restaurants.Finally, the hosts were wonderfully...
United States
Lee M.
The price is AU$935
includes taxes & fees
16 Nov - 17 Nov
Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront
Exterior
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, (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 AU$260
includes taxes & fees
17 Nov - 18 Nov
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Exterior
Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails

Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails

Lexington
10.0 out of 10, Exceptional, (1)
"My partner and I hoped for a peaceful getaway to hike and chose this place. As soon as we drove in, it seemed like nothing we’d quite seen. It’s walled like a park with an expansive front yard area, but it’s private. There are really cute old buildings. It was like we had the place to ourselves. There’s a kitchen and plenty of room in the sleeping building. Things were really clean and nice with a coffee welcome tray. Took a walk up to a little lake, and then hiked into the woods -...
United States
T D.
The price is AU$1,209
includes taxes & fees
26 Nov - 27 Nov
Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails
Fridge, microwave, oven, stovetop
"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, (12)
"We thought the house was great and the location was perfect! We would definitely stay there again. "
United States
Tom or Karen K.
The price is AU$562
includes taxes & fees
19 Nov - 20 Nov
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Smart TV
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, (19)
"Great one bedroom apartment! It was clean and great location for our quick getaway."
United States
Eric S.
The price is AU$331
includes taxes & fees
16 Nov - 17 Nov
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Interior
#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown

Madison
10.0 out of 10, Exceptional, (35)
"Beautiful and well cared for in the midst of downtown activity and close to Crystal Beach Pool!"
United States
Charles G.
The price is AU$704
includes taxes & fees
16 Nov - 17 Nov
#207 King Suites, River Views, Deck, Downtown
1 bedroom, WiFi, bed sheets
East Main Lofts - Boho 203

East Main Lofts - Boho 203

Madison
9.6 out of 10, Exceptional, (8)
"Nice, clean overnight stay. A little loud outside"
United States
Gary H.
The price is AU$540
includes taxes & fees
23 Nov - 24 Nov
East Main Lofts - Boho 203
Outdoor dining
"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit

"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit

Madison
9.6 out of 10, Exceptional, (12)
"The house was exactly as described and communications were excellent. We really enjoyed our stay and it was a perfect location."
United States
Cynthia W.
The price is AU$580
includes taxes & fees
23 Nov - 24 Nov
"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit
4 bedrooms
East Main Lofts -Roller Rink 301

East Main Lofts -Roller Rink 301

Madison
10.0 out of 10, Exceptional, (7)
"What a Christmas gift this property was for our extended family! Beautiful and fun location! Thank you!"
United States
Kristan N.
The price is AU$1,516
includes taxes & fees
23 Nov - 24 Nov
East Main Lofts -Roller Rink 301
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

Riverboat Inn and Suites

Riverboat Inn and Suites

10/10 Excellent
"The room and staff were great. Enjoyed our stay."
Katrina 1-night trip
Posted 2 days ago
Riverboat Inn and Suites

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 favourite 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 depend 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 AU$202 per night. Entering your travel dates in the search wizard might find you 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.