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Chelsea Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Chelsea vacation rentals

A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

1. 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 CA $60
CA $246 total
includes taxes & fees
Oct 25 - Oct 26
Modern cabin very close to scenic riverfront walks
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

2. 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
9.0 out of 10, Wonderful, (14 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is CA $87
CA $167 total
includes taxes & fees
Nov 16 - Nov 17
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A wooden cabin with a porch, a staircase, and a deck.

3. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (19 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is CA $119
CA $226 total
includes taxes & fees
Nov 9 - Nov 10
Sassafras Woodland Cabin at Lost Trails
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

4. 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 CA $183
CA $379 total
includes taxes & fees
Oct 25 - Oct 26
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Property grounds

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

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (18 reviews)
"Host was very accommodating and this place was perfect for a place to stay while visiting friends. Everything was very comfortable, especially the very soft bed!! "
United States
C J.
The price is CA $125
CA $240 total
includes taxes & fees
Nov 2 - Nov 3
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
cd294e93-b148-4eb4-b858-151fabf1d0ec

6. 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 CA $140
CA $252 total
includes taxes & fees
Nov 18 - Nov 19
Maple Cozy Cabin at Lost Trails
A cozy room with a bed, a chair, a sofa, and a small table.

7. 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 CA $131
CA $247 total
includes taxes & fees
Nov 9 - Nov 10
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
A wooden deck with wicker furniture and a ceiling fan.

8. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (31 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is CA $140
CA $242 total
includes taxes & fees
Oct 26 - Oct 27
Cedar Rustic Cabin at Lost Trails
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

9. Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is CA $140
CA $252 total
includes taxes & fees
Nov 16 - Nov 17
Walnut Secluded Cabin at Lost Trails
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

10. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"This is a total hidden gem! The cabin seemed brand new and was outfitted with everything you might need. We spent our 25th wedding anniversary weekend here and loved every second! Would highly recommend!"
United States
Jodi E.
The price is CA $140
CA $252 total
includes taxes & fees
Oct 25 - Oct 26
Mulberry Secluded Cabin at Lost Trails
A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

11. 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 CA $148
CA $223 total
includes taxes & fees
Oct 26 - Oct 27
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

12. The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Madison Historic District
9.8 out of 10, Exceptional, (13 reviews)
"We enjoyed our visit and would recommend to others looking for a convenient location and comfortable stay."
United States
Renee M.
The price is CA $91
CA $165 total
includes taxes & fees
Nov 8 - Nov 9
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

13. 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, (78 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 CA $151
CA $317 total
includes taxes & fees
Oct 29 - Oct 30
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A log cabin with a fire pit and outdoor seating.

14. 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 CA $227
CA $613 total
includes taxes & fees
Nov 5 - Nov 6
Family-friendly cabin with game room and backyard!
A Blackstone grill with a propane tank, set up outdoors with a view of a lake and trees.

15. 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 CA $174
CA $405 total
includes taxes & fees
Oct 25 - Oct 26
River Retreat
A covered porch with a wooden door, potted plants, and a metal railing.

16. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Very cool house in a nice neighborhood. Had everything we needed and was close to anything you want to do in Madison. We will definitely stay there again!"
United States
Dean C.
The price is CA $192
CA $365 total
includes taxes & fees
Nov 15 - Nov 16
The Artist’s A-Frame
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

17. The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison Historic District
9.6 out of 10, Exceptional, (23 reviews)
"Our room was so cute and perfect for a couple. We loved it! The location was perfect as well!"
United States
Stee
The price is CA $115
CA $197 total
includes taxes & fees
Nov 3 - Nov 4
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

18. The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205

The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205
Madison Historic District
9.8 out of 10, Exceptional, (7 reviews)
"Cozy, peaceful, wonderful with great location. "
United Kingdom
Ed E.
The price is CA $88
CA $169 total
includes taxes & fees
Oct 29 - Oct 30
The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

19. 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 CA $170
CA $323 total
includes taxes & fees
Oct 28 - Oct 29
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

20. The Madison Inn, Historic city overlook suite 206, Historic city overlook suite 306

The Madison Inn, Historic city overlook suite 206, Historic city overlook suite 306
Madison Historic District
9.2 out of 10, Wonderful, (10 reviews)
"Very nice property for weekend visit."
United States
Mark S.
The price is CA $91
CA $172 total
includes taxes & fees
Nov 16 - Nov 17
The Madison Inn, Historic city overlook suite 206, Historic city overlook suite 306
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

Hillside Inn

Hillside Inn

10/10 Excellent
"My husband and I enjoyed our overnight stay. The front desk clerk was kind and helpful. She made us a personal copy of Madison’s activities for the day. Our balcony gave us a beautiful view of the Ohio River as well as downtown Madison. We’d definitely stay here again."
Kerri 1-night trip
Posted 19 hours ago
Hillside Inn

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chelsea vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chelsea vacation rentals we have selected for you start as low as CA $197 per night. Entering your travel dates in the search wizard 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. 

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.