Chelsea Holiday Rentals

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Holiday Rentals in Chelsea

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, (40)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is NZ$375
includes taxes & fees
29 Sept - 30 Sept
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (11)
"Really enjoyed our stay. Super easy to find, plenty of parking. Walking distance of the shops. 10/10 would stay again."
The price is NZ$291
includes taxes & fees
29 Sept - 30 Sept
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Rustic cabin just outside of Madison!
4 bedrooms, free WiFi, bed sheets

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (45)
"It was a very nice and clean property, and it was a very relaxing vacation. Crossing the creek very amazing. And our host offered a very comforting place and enjoyed the seeing this part of Indiana. "
Rustic cabin just outside of Madison!
Bungalow on Main!!
Exterior

Bungalow on Main!!

9.8 out of 10, Exceptional, (19)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!
Charming 3-bedroom house in lovely downtown Madison.
Exterior

Charming 3-bedroom house in lovely downtown Madison.

2.0 star property
9.4 out of 10, Exceptional, (3)
"Great old home and cool neighborhood. "
Charming 3-bedroom house in lovely downtown Madison.
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (11)
"We thoroughly enjoyed our time there, and the little extra touches were a pleasant surprise! The house was incredibly clean and the owner was very prompt and responsive to questions we had. Definitely would stay again!"
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn
Outdoor spa tub

Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn

10.0 out of 10, Exceptional, (10)
"This was such a nice place, very quiet and peaceful. The property was everything we had hoped for and the host was so nice and helpful."
The price is NZ$558
includes taxes & fees
8 Oct - 9 Oct
Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn
Relaxing Country Getaway
Interior

Relaxing Country Getaway

9.4 out of 10, Exceptional, (39)
"It was a very nice little get away without going too far. Everything was clean, including the hot tub. We will definitely keep this place in mind in the future!"
Relaxing Country Getaway
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, (52)
"Perfect location with a fantastic host! I stay at this location every time I visit Madison. It’s close to everything historic Madison has to offer. If coming to town I cannot recommend this place enough. Book it, you will not be disappointed."
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Exterior detail

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

9.8 out of 10, Exceptional, (30)
"The house was clean, great location. Would stay again"
The price is NZ$431
includes taxes & fees
28 Sept - 29 Sept
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
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, (200)
"Very nice log cabin in a very secluded location with a small pond.We enjoyed it very much."
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Fridge, microwave, oven, stovetop

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

9.6 out of 10, Exceptional, (18)
"Perfect little cozy cabin for an amazing getaway! We were able to just relax and enjoy our time together with zero distractions. 10/10 would definitely stay here again! "
The price is NZ$359
includes taxes & fees
29 Sept - 30 Sept
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Historic city overlook suite 206, Historic city overlook suite 306
1 bedroom

Historic city overlook suite 206, Historic city overlook suite 306

9.4 out of 10, Exceptional, (8)
"Very clean and cozy! Nice area close to town. "
The price is NZ$270
includes taxes & fees
29 Sept - 30 Sept
Historic city overlook suite 206, Historic city overlook suite 306
Sunset over the city Suite 201, Sunset over the city Suite 201
Interior

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

9.6 out of 10, Exceptional, (9)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
The price is NZ$235
includes taxes & fees
1 Oct - 2 Oct
Sunset over the city Suite 201, Sunset over the city Suite 201
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, (149)
"Had a group of friends stay for a weekend trip, property is well maintained and has fantastic amenities. "
The price is NZ$735
includes taxes & fees
28 Sept - 29 Sept
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (56)
"Home was the perfect setting for our yearly girl’s get together!"
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
The Artist’s A-Frame
Exterior

The Artist’s A-Frame

10.0 out of 10, Exceptional, (22)
"I can't say enough about our stay at the Artist's A-Frame. The hosts are exceptional, the location is ideal, and the space is beautiful! I highly recommend and am anxious to return!"
The price is NZ$418
includes taxes & fees
28 Oct - 29 Oct
The Artist’s A-Frame
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (1)
"It was lovely!"
The price is NZ$839
includes taxes & fees
28 Oct - 29 Oct
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Sassafras Cabin at Lost Trails
Exterior

Sassafras Cabin at Lost Trails

10.0 out of 10, Exceptional, (2)
"My stay was very nice. I should note that I actually stayed in the Mulberry unit and my review of it is that it’s nicely situated in a private setting compared to the other units. Everything is quite new and well appointed. Great quality of kitchenware and linens. Comfortable bed. Lovely outdoor setting. Very close to town but far enough to feel like you’re in the woods. "
Sassafras Cabin at Lost Trails
Cozy Cabin Madison Indiana
TV, fireplace

Cozy Cabin Madison Indiana

10.0 out of 10, Exceptional, (17)
"The cabin was just as described online it's very quiet and was the perfect getaway "
Cozy Cabin Madison Indiana
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 staff was great… it was very very clean… View was incredible if you can get a Riverview… Make sure you know what building you are going to be put in. There’s the main one with the bar where all the action is and then there’s one close by that is also theirs, but they show you back-and-forth in a golf cart if you want. We had entertainment on the weekend and the breakfast was certainly sufficient."
Sally 2-night trip
Posted 4 days ago
Riverboat Inn and Suites

Find out more about Chelsea

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$235 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.