Chelsea Vacation Rentals

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Check prices for these dates

Tonight
Dec 6 - Dec 7
Tomorrow
Dec 7 - Dec 8
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Vacation Rentals in Chelsea

4 bedrooms, free WiFi, bed sheets
Rustic cabin just outside of Madison!

Cabin in Madison

10.0 out of 10, Exceptional, (53)
"Great day, we loved the cabin!"
United States
Mark C.
Rustic cabin just outside of Madison!
Interior
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Apartment in Madison

10.0 out of 10, Exceptional, (61)
"This was the best place I have ever stayed. The place was amazing and the hospitality exceeded expectations. I would definitely recommend staying here. "
United States
Adam K.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Apartment in Madison

10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is ￥13,264
￥28,634 total
includes taxes & fees
Dec 7 - Dec 8
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Vacation Home in Madison

9.8 out of 10, Exceptional, (51)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
The price is ￥19,391
￥38,534 total
includes taxes & fees
Dec 7 - Dec 8
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior
Cozy Tiny House in Scottsburg

Vacation Home in Scottsburg

9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is ￥12,255
￥26,757 total
includes taxes & fees
Dec 29 - Dec 30
Cozy Tiny House in Scottsburg
Exterior detail
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

Vacation Home in Hanover

9.8 out of 10, Exceptional, (33)
"Great place to stay for Hanover college "
United States
Lindsey M.
The price is ￥18,034
￥38,960 total
includes taxes & fees
Dec 7 - Dec 8
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Exterior
Sleeps 4, Rustic, Secluded

Vacation Home in Lexington

8.0 out of 10, Very Good, (4)
"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 ￥16,971
￥35,416 total
includes taxes & fees
Dec 8 - Dec 9
Sleeps 4, Rustic, Secluded
Exterior
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Apartment in Madison

2.0 star property
10.0 out of 10, Exceptional, (14)
"We could not have been happier with this cute little place. Wonderful location with easy walking access to both the riverfront and all Madison had to offer with shops and dining options. We would not hesitate to stay here again!"
United States
Gary W.
The price is ￥19,546
￥26,046 total
includes taxes & fees
Dec 9 - Dec 10
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Smart TV, fireplace, video games, DVD player
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Cabin in Henryville

10.0 out of 10, Exceptional, (153)
"This is beautiful property and thoughtful amenities. The host is super responsive. We cannot wait to plan our next stay. "
United States
Katie A.
The price is ￥34,904
￥74,150 total
includes taxes & fees
Dec 11 - Dec 12
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Interior
#207 King Suites, River Views, Deck, Downtown

Vacation Home in Madison

10.0 out of 10, Exceptional, (36)
"This is a beautiful historic house. Everything was neat, clean and perfect working order. Will definitely stay there again."
United States
Rick M.
The price is ￥30,871
￥67,337 total
includes taxes & fees
Dec 7 - Dec 8
#207 King Suites, River Views, Deck, Downtown
Property grounds
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Apartment in Madison

9.8 out of 10, Exceptional, (10)
"Super comfortable, clean little apartment in a quiet area off the main strip. We loved out stay!"
United States
Courtney G.
The price is ￥11,805
￥20,037 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Property grounds
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Cabin in Madison

10.0 out of 10, Exceptional, (209)
"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
1 bedroom, WiFi, bed sheets
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

Apartment in 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 ￥12,959
￥22,099 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Microwave, oven, stovetop
Charming 2-bedroom house with a river view in wonderful Madison

Vacation Home in Madison

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot walkable to downtown Madison & the river area. Appreciated how well-stocked the kitchen, bathroom, and laundry were. And being able to bring a pet was a big plus."
United States
Chelsea C.
Charming 2-bedroom house with a river view in wonderful Madison
Exterior
The Artist’s A-Frame

Vacation Home in Madison

10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
The price is ￥19,546
￥37,820 total
includes taxes & fees
Dec 18 - Dec 19
The Artist’s A-Frame
Terrace/patio
Family/Pet-Friendly Riverside Home w/Amazing Views

Vacation Home in Prospect

9.0 out of 10, Wonderful, (22)
"This was our second stay at the River house. We had a great stay!! I Love the view from the deck!! "
United States
Rachel R.
Family/Pet-Friendly Riverside Home w/Amazing Views
Exterior
Charming 3-bedroom house in lovely downtown Madison.

Vacation Home in Madison

2.0 star property
9.4 out of 10, Exceptional, (11)
"Great old home and cool neighborhood. "
United States
Randy S.
Charming 3-bedroom house in lovely downtown Madison.
Interior
Stoney Creek - Sit back and unwind

Cabin in Madison

10.0 out of 10, Exceptional, (102)
"Close enough to be convenient to local attractions, out enough to be mostly quiet. "
United States
Garry B.
Stoney Creek - Sit back and unwind
Interior
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Vacation Home in Charlestown

10.0 out of 10, Exceptional, (12)
"The property was clean and quiet. Great location in a nice residential neighborhood. Very close to Charlestown State Park where we did some hiking."
United States
Chris S.
The price is ￥14,737
￥22,788 total
includes taxes & fees
Dec 7 - Dec 8
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Fridge, microwave, oven, stovetop
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

Vacation Home in Madison

10.0 out of 10, Exceptional, (12)
"Madison Manor II was perfect for our annual girls trip. We were comfortable, location was great, the home was very clean."
United States
Carissa N.
The price is ￥23,580
￥56,196 total
includes taxes & fees
Dec 7 - Dec 8
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
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

Red Roof Inn Scottsburg

Red Roof Inn Scottsburg

10/10 Excellent
"Clean room friendly staff"
Marci 1-night trip
Posted 4 days ago
Red Roof Inn Scottsburg

Find out more about Chelsea

Search for holiday rentals in Chelsea on Expedia! You can easily find your home rentals, villas, holiday apartments in Chelsea using one of the methods below:

  • View our selection of featured holiday rentals in Chelsea
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Look no further and take a look at our great range of rental properties in Chelsea!

Frequently asked questions

Can I find a vacation rental in Chelsea?

Yes, you can find vacation rentals close to the most popular sights in Chelsea, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Chelsea has to offer?

Cozy Tiny House in Scottsburg: This vacation home rental near Chelsea has air-conditioning and laundry facilities 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 Hardy Lake. In the larger area, you’ll find Clifty Falls State Park and Lanthier Winery.

What’s a vacation rental in Chelsea like?

Vacation rentals are privately owned properties you can book for several days or longer in Chelsea. Vacation rentals offer amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for family trips.