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Chelsea Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chelsea vacation rentals

A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

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

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover
9.6 out of 10, Exceptional, (54 reviews)
"Great place to stay for touring in historic Madison Indiana!"
United States
Linda G.
The price is ￥20,575
￥42,518 total
includes taxes & fees
Nov 1 - Nov 2
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A two-story house with a garage, a stone facade, and a well-maintained lawn.

2. 3BR Home Near Hanover College & Madison

3BR Home Near Hanover College & Madison
Hanover
The price is ￥34,685
￥71,436 total
includes taxes & fees
Nov 8 - Nov 9
3BR Home Near Hanover College & Madison
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

3. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
9.4 out of 10, Exceptional, (20 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
United States
MaKayla Q.
The price is ￥7,321
￥38,698 total
includes taxes & fees
Nov 1 - Nov 2
Modern cabin very close to scenic riverfront walks
A kitchen with a central island, wooden stools, a trash bin, and a hanging plant arrangement.

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

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Hanover
9.4 out of 10, Exceptional, (8 reviews)
"It was lovely!"
United States
Carolyne R.
The price is ￥31,926
￥74,791 total
includes taxes & fees
Nov 2 - Nov 3
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
A log cabin with a fire pit and outdoor seating.

5. Family-friendly cabin with game room and backyard!

Family-friendly cabin with game room and backyard!
Hanover
10.0 out of 10, Exceptional, (4 reviews)
"Host is very easy to communicate with and the property provided us with great memories! Would definitely stay here again!"
United States
Eli H.
The price is ￥27,433
￥91,834 total
includes taxes & fees
Nov 4 - Nov 5
Family-friendly cabin with game room and backyard!
An outdoor patio with a view of a lake, featuring a table and chairs, an American flag, and a hanging light fixture.

6. T&E Riverhouse Retreat

T&E Riverhouse Retreat
Hanover
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful view of the river! Nice location and easy to find. Highly recommend for a group getaway. "
United States
Beverly L.
The price is ￥36,080
￥66,521 total
includes taxes & fees
Nov 2 - Nov 3
T&E Riverhouse Retreat
A covered porch with a wooden door, potted plants, and a metal railing.

7. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Great experience. Definitely recommend staying here if you’re visiting Madison. Great location to down town,"
United States
Mike H.
The price is ￥21,599
￥40,881 total
includes taxes & fees
Nov 2 - Nov 3
The Artist’s A-Frame
Property grounds

8. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.4 out of 10, Exceptional, (19 reviews)
"Clean and cozy"
United States
Julie
The price is ￥14,057
￥27,053 total
includes taxes & fees
Nov 2 - Nov 3
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A Blackstone grill with a propane tank, set up outdoors with a view of a lake and trees.

9. River Retreat

River Retreat
Charlestown
10.0 out of 10, Exceptional, (1 review)
"Easy check in. Nice cozy home right by the river. Even left a golf cart for use when staying!"
United States
Brady S.
The price is ￥19,550
￥45,074 total
includes taxes & fees
Nov 30 - Dec 1
River Retreat
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

10. The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Madison Historic District
9.2 out of 10, Wonderful, (15 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is ￥9,743
￥18,782 total
includes taxes & fees
Nov 18 - Nov 19
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A cozy room with a bed, a chair, a sofa, and a small table.

11. Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Madison Historic District
9.6 out of 10, Exceptional, (9 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is ￥14,767
￥27,868 total
includes taxes & fees
Nov 9 - Nov 10
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
A wooden cabin with a porch, a staircase, and a deck.

12. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (20 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is ￥14,042
￥26,282 total
includes taxes & fees
Nov 18 - Nov 19
Sassafras Woodland Cabin at Lost Trails
A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

13. Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (27 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
United States
Pam
The price is ￥16,724
￥25,138 total
includes taxes & fees
Nov 3 - Nov 4
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A room with a bed, two armchairs, a small table, and a microwave.

14. Tiny Lakeside Cottage I 50 Acres of Gardens

Tiny Lakeside Cottage I 50 Acres of Gardens
Henryville
10.0 out of 10, Exceptional, (1 review)
"Awesome place in a gated property. The tiny home is exactly as pictured. Will 100% stay here again for future Henryville visits to see family."
United States
Jonathan B.
The price is ￥22,025
￥49,738 total
includes taxes & fees
Nov 2 - Nov 3
Tiny Lakeside Cottage I 50 Acres of Gardens
A modern living room with a fireplace, a flat-screen TV mounted above it, and a staircase with wooden steps.

15. NEW! Historic, Walk to Main St, King Suites, Patio

NEW! Historic, Walk to Main St, King Suites, Patio
Madison Historic District
10.0 out of 10, Exceptional, (1 review)
"Great property and a lot of room which was great."
United States
Kathryn B.
The price is ￥23,405
￥49,563 total
includes taxes & fees
Nov 3 - Nov 4
NEW! Historic, Walk to Main St, King Suites, Patio
A dining area with a wooden table set for six, surrounded by chairs.

16. #207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown
Madison Historic District
10.0 out of 10, Exceptional, (48 reviews)
"Loved this place, very clean and well stocked with the little extras that you always seem to need. "
United States
Matt C.
The price is ￥32,477
￥69,941 total
includes taxes & fees
Nov 1 - Nov 2
#207 King Suites, River Views, Deck, Downtown
2

17. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is ￥15,766
￥28,379 total
includes taxes & fees
Nov 30 - Dec 1
Maple Cozy Cabin at Lost Trails
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

18. The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (51 reviews)
"Had a very nice stay"
United States
Brad P.
The price is ￥19,169
￥36,379 total
includes taxes & fees
Nov 3 - Nov 4
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
A rustic cabin with a porch, stone walls, and an American flag.

19. Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Henryville
10.0 out of 10, Exceptional, (175 reviews)
"Great host, clean house in a great location. We really enjoyed our stay."
United States
Michael S.
The price is ￥33,424
￥76,785 total
includes taxes & fees
Nov 11 - Nov 12
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

20. Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (79 reviews)
"The place is very clean, also convenient and close to down town. Check in and everything was very smooth! I recommend this cute little place especially for young families."
United States
Kyle A.
The price is ￥17,039
￥35,380 total
includes taxes & fees
Nov 1 - Nov 2
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
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

8/10 Good
"This is our second time staying at the Riverboat Inn. The staff is so very helpful and so very nice. They do whatever they can to make your stay good. The rooms are clean and well kept. Will definitely stay again on our next trip to Madison."
Brett 1-night trip
Posted 5 hours ago
Riverboat Inn and Suites

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?

Red comfy cottage : This vacation home rental near Chelsea offers an indoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.