Chelsea Vacation Rentals

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Dec 6 - Dec 7
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Dec 7 - Dec 8
Next weekend
Dec 12 - Dec 14
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Dec 19 - Dec 21

Vacation Rentals in Chelsea

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

Apartment in Madison

9.6 out of 10, Exceptional, (13)
"Quick and easy one night stay. Comfy bed. Didn’t use much in the space but seemed well stocked. Clean and cozy property. Will definitely stay here again. "
United States
Christy H.
Sunset over the city Suite 201, Sunset over the city Suite 201
Outdoor dining
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

Vacation Home in Madison

9.6 out of 10, Exceptional, (12)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is ￥24,976
￥56,553 total
includes taxes & fees
Dec 11 - Dec 12
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
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!
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
Fridge, microwave, oven, stovetop
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

Vacation Home in Pendleton

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.
The price is ￥13,651
￥36,255 total
includes taxes & fees
Dec 13 - Dec 14
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
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
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
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
Fridge, microwave, oven, stovetop
#209 Kings, River View, Deck, Bicentennial Park

Vacation Home in Madison

10.0 out of 10, Exceptional, (62)
"Amazing stay in an beautiful town. Easy access to charming shops and restaurants. "
United States
Kyle L.
The price is ￥30,871
￥67,337 total
includes taxes & fees
Dec 7 - Dec 8
#209 Kings, River View, Deck, Bicentennial Park
1 bedroom, WiFi, bed sheets
East Main Lofts - Boho 203

Apartment in Madison

9.6 out of 10, Exceptional, (8)
"Very tasteful loft in convenient location. Enjoyed our stay."
United States
Teresa P.
The price is ￥30,561
￥54,234 total
includes taxes & fees
Dec 7 - Dec 8
East Main Lofts - Boho 203
Exterior detail
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cottage in Madison

2.0 star property
The price is ￥12,286
￥24,833 total
includes taxes & fees
Dec 7 - Dec 8
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic 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
Fridge, microwave, oven, stovetop
Emerald Lake Retreat Charlestown

Vacation Home in 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.
The price is ￥19,391
￥72,047 total
includes taxes & fees
Dec 12 - Dec 13
Emerald Lake Retreat Charlestown
Fridge, microwave, oven, stovetop
Modern Nature Cabin | Private Escape in the Forest

Vacation Home in Hanover

9.8 out of 10, Exceptional, (7)
"Very nice facility and relaxing setting . "
United States
Robert V.
The price is ￥13,952
￥33,977 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Modern Nature Cabin | Private Escape in the Forest
Fridge, microwave, oven, stovetop
Country home with beautiful views and access to hiking, biking, and horse trails

Vacation Home in Henryville

10.0 out of 10, Exceptional, (28)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is ￥23,067
￥38,536 total
includes taxes & fees
Dec 8 - Dec 9
Country home with beautiful views and access to hiking, biking, and horse trails
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
Microwave, oven, stovetop, dishwasher
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

Vacation Home in Hanover

9.0 out of 10, Wonderful, (4)
"The Hanover House was very large, nicely furnished and the sunrise and sunsets were beautiful. A perfect getaway for a group of friends. Plenty of room to spread out and play games. Very relaxing, close to restaurants, shopping and site seeing. The host was extremely friendly and very helpful and quick to respond. We would definitely stay there again!!!"
United States
Deborah D.
The price is ￥30,716
￥72,609 total
includes taxes & fees
Dec 7 - Dec 8
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
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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  • Enter your travel dates to view the best deals on holiday rentals in Chelsea while they last

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.