Search Vacation Homes in Chelsea

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Chelsea vacation homes

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

Vacation Home in Pendleton

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
9.8 out of 10, Exceptional, (62)
"Came to the area for a funeral. Worked out great for our needs. Alecia was quick to respond any time we called. Enjoyed it. "
United Kingdom
Clyde C.
$205 nightly
The price is $226
Jan 4 - Jan 5, 2026
Total with taxes and fees
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Interior
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.
$383 nightly
The price is $433
Dec 18 - Dec 19
Total with taxes and fees
Emerald Lake Retreat Charlestown
Fridge, microwave, oven, stovetop
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 14 - Dec 15
Total with taxes and fees
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Terrace/patio
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
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 21 - Dec 22
Total with taxes and fees
Modern Nature Cabin | Private Escape in the Forest
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 6 - Jan 7, 2026
Total with taxes and fees
The Artist’s A-Frame
Smart TV
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
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 15 - Dec 16
Total with taxes and fees
Sleeps 4, Rustic, Secluded
Smart TV
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

Vacation Home in Hanover

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
9.8 out of 10, Exceptional, (34)
"Great place to stay for Hanover college "
United States
Lindsey M.
$233 nightly
The price is $268
Dec 28 - Dec 29
Total with taxes and fees
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
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 14 - Dec 15
Total with taxes and fees
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
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)
$388 nightly
The price is $446
Dec 14 - Dec 15
Total with taxes and fees
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
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, (28)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
$225 nightly
The price is $251
Dec 14 - Dec 15
Total with taxes and fees
Country home with beautiful views and access to hiking, biking, and horse trails
Exterior detail
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
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 14 - Dec 15
Total with taxes and fees
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
Pool
#207 King Suites, River Views, Deck, Downtown

Vacation Home in Madison

#207 King Suites, River Views, Deck, Downtown
10.0 out of 10, Exceptional, (37)
"This is a beautiful historic house. Everything was neat, clean and perfect working order. Will definitely stay there again."
United States
Rick M.
$366 nightly
The price is $431
Dec 16 - Dec 17
Total with taxes and fees
#207 King Suites, River Views, Deck, Downtown
Property grounds
Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails

Vacation Home in Lexington

Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails
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.
$691 nightly
The price is $774
Dec 18 - Dec 19
Total with taxes and fees
Relaxing 7- bedroom Retreat Center, Glamping style. 250 acres, hiking trails
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 14 - Dec 15
Total with taxes and fees
Pendleton, KY Farm in Oldham Co
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.
$899 nightly
The price is $985
Dec 22 - Dec 23
Total with taxes and fees
NYE Getaway! Hot Tub, Game Rooms, 20 min to Lou
Private kitchen
Madison Manor By the River: Sleeps up to 15, Walk to Historic Downtown

Vacation Home in Madison

Madison Manor By the River: Sleeps up to 15, Walk to Historic Downtown
2.0 star property
$618 nightly
The price is $711
Dec 14 - Dec 15
Total with taxes and fees
Madison Manor By the River: Sleeps up to 15, Walk to Historic Downtown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 2 days ago
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Find out more about Chelsea

Chelsea Vacation Homes information

Number of reviews
314
Accommodation
65 Vacation Homes
Lowest Price
$147
Highest Price
$985

Explore a world of travel with Expedia