Chelsea Vacation Rentals

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Check prices for these dates

Tonight
Dec 15 - Dec 16
Tomorrow
Dec 16 - Dec 17
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Chelsea vacation rentals

Fridge, microwave, oven, stovetop
Emerald Lake Retreat Charlestown

Vacation Home in Charlestown

Emerald Lake Retreat Charlestown
10.0 out of 10, Exceptional, (3)
"This a great place for families to gather. It's very spacious and clean and comfortable. And though it's in a quiet and peaceful area with a small lake at the base of the property, places to eat and get groceries are just a short drive away. There's a wonderful seating area around a firepit, too!"
United States
Kelly P.
$371 nightly
The price is $419
Dec 16 - Dec 17
Total with taxes and fees
Emerald Lake Retreat Charlestown
Exterior
Sleeps 4, Rustic, Secluded

Vacation Home in Lexington

Sleeps 4, Rustic, Secluded
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.
$214 nightly
The price is $218
Dec 16 - Dec 17
Total with taxes and fees
Sleeps 4, Rustic, Secluded
Interior
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Vacation Home in Charlestown

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
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.
$130 nightly
The price is $147
Dec 16 - Dec 17
Total with taxes and fees
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Exterior
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Apartment in Madison

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
2.0 star property
10.0 out of 10, Exceptional, (15)
"Great little place. Location was exceptional. "
United States
Andrew P.
$106 nightly
The price is $122
Dec 16 - Dec 17
Total with taxes and fees
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Exterior detail
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cottage in Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
2.0 star property
$139 nightly
The price is $160
Dec 16 - Dec 17
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Terrace/patio
Pendleton, KY Farm in Oldham Co

Vacation Home in Pendleton

Pendleton, KY Farm in Oldham Co
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.
$856 nightly
The price is $944
Dec 17 - Dec 18
Total with taxes and fees
Pendleton, KY Farm in Oldham Co
Property grounds
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Apartment in Madison

The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
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.
$129 nightly
The price is $132
Dec 16 - Dec 17
Total with taxes and fees
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Vacation Home in Madison

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
9.8 out of 10, Exceptional, (53)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
$217 nightly
The price is $250
Dec 16 - Dec 17
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior
Cozy Tiny House in Scottsburg

Vacation Home in Scottsburg

Cozy Tiny House in Scottsburg
9.6 out of 10, Exceptional, (4)
"Wonderful accommodations. Comfortable and clean. We enjoyed our stay. I am sure we will return as Hope was a great host."
United States
Karen P.
$154 nightly
The price is $172
Dec 29 - Dec 30
Total with taxes and fees
Cozy Tiny House in Scottsburg
Smart TV, fireplace, video games, DVD player
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Cabin in Henryville

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
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.
$423 nightly
The price is $478
Dec 16 - Dec 17
Total with taxes and fees
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Fridge, microwave, oven, stovetop
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Cabin in Madison

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
9.6 out of 10, Exceptional, (20)
"My wife and I enjoyed our stay here while checking out Madison. Great location, nicely decorated. "
United States
Justin L.
$252 nightly
The price is $290
Dec 16 - Dec 17
Total with taxes and fees
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Microwave, oven, stovetop, dishwasher
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

Vacation Home in Hanover

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
9.2 out of 10, Wonderful, (5)
"It was lovely!"
United States
Carolyne R.
$388 nightly
The price is $446
Dec 17 - Dec 18
Total with taxes and fees
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Exterior
The Sweet Retreat Wheelchair Accessible Historic Home

Vacation Home in La Grange

The Sweet Retreat Wheelchair Accessible Historic Home
2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a family gathering over Thanksgiving and the large table was very nice and appreciated. Host was very prompt with communication and most everything we needed was there. Would stay again!"
United States
Shelley S.
$283 nightly
The price is $321
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Sweet Retreat Wheelchair Accessible Historic Home
Fridge, microwave, oven, stovetop
Country home with beautiful views and access to hiking, biking, and horse trails

Vacation Home in Henryville

Country home with beautiful views and access to hiking, biking, and horse trails
10.0 out of 10, Exceptional, (29)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
$225 nightly
The price is $251
Dec 20 - Dec 21
Total with taxes and fees
Country home with beautiful views and access to hiking, biking, and horse trails
Exterior
The Artist’s A-Frame

Vacation Home in Madison

The Artist’s A-Frame
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
$196 nightly
The price is $225
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Artist’s A-Frame
Lobby
Modern Nature Cabin | Private Escape in the Forest

Vacation Home in Hanover

Modern Nature Cabin | Private Escape in the Forest
9.8 out of 10, Exceptional, (7)
"Very nice facility and relaxing setting . "
United States
Robert V.
$175 nightly
The price is $185
Dec 22 - Dec 23
Total with taxes and fees
Modern Nature Cabin | Private Escape in the Forest
Fridge, microwave, oven, stovetop
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

Vacation Home in Madison

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
10.0 out of 10, Exceptional, (14)
"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.
$313 nightly
The price is $360
Dec 16 - Dec 17
Total with taxes and fees
"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

Apartment in Madison

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
$161 nightly
The price is $185
Dec 16 - Dec 17
Total with taxes and fees
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Outdoor dining
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

Vacation Home in Madison

"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
9.6 out of 10, Exceptional, (12)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
$324 nightly
The price is $373
Dec 17 - Dec 18
Total with taxes and fees
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
Dining
NYE Getaway! Hot Tub, Game Rooms, 20 min to Lou

Vacation Home in La Grange

NYE Getaway! Hot Tub, Game Rooms, 20 min to Lou
10.0 out of 10, Exceptional, (18)
"Had such a wonderful stay! The house was beautiful, fun and exactly as described. The host Deb was responsive, and made everything easy for us. Would definitely stay again! "
United States
Kasey H.
$874 nightly
The price is $957
Dec 22 - Dec 23
Total with taxes and fees
NYE Getaway! Hot Tub, Game Rooms, 20 min to Lou
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

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

10/10 Excellent
"Exceptional facility. Perfect every time."
Robert 1-night trip
Posted 3 days ago
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Find out more about Chelsea

Everything you need to know about Chelsea vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chelsea vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chelsea vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chelsea in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $122 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chelsea rentals

At Expedia, we put the best Chelsea vacation 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 vacation.

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

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?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: This vacation home rental near 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 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.