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Chelsea Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chelsea vacation rentals

A covered outdoor deck with a table and chairs, a ceiling fan, and a view of a body of water.

1. T&E Riverhouse Retreat

T&E Riverhouse Retreat
Hanover
10.0 out of 10, Exceptional, (13 reviews)
"Located in a quiet area with great river views. Well stocked kitchen. Would stay there again"
United States
Phil T.
$396 nightly
The price is $448
Nov 1 - Nov 2
Total with taxes and fees
T&E Riverhouse Retreat
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

2. 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, (53 reviews)
"Close to downtown Madison and Clifty Falls, this place had everything we needed to visit the area and relax I'm the evening."
United States
Maggie D.
$235 nightly
The price is $270
Oct 4 - Oct 5
Total with taxes and fees
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A log cabin with a fire pit and outdoor seating.

3. Spacious family cabin with game room and backyard!

Spacious family cabin with game room and backyard!
Hanover
9.4 out of 10, Exceptional, (3 reviews)
"Property is beautiful"
United States
Barb N.
$574 nightly
The price is $620
Oct 12 - Oct 13
Total with taxes and fees
Spacious family cabin with game room and backyard!
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
9.0 out of 10, Wonderful, (6 reviews)
"It was lovely!"
United States
Carolyne R.
$404 nightly
The price is $465
Oct 5 - Oct 6
Total with taxes and fees
The Hanover Haven - Slice of Paradise - 10 minutes 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, (17 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.
$149 nightly
The price is $171
Oct 5 - Oct 6
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and gravel.

6. 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.
$197 nightly
The price is $211
Oct 12 - Oct 13
Total with taxes and fees
Modern cabin very close to scenic riverfront walks
An aerial view of a water park with multiple swimming pools, slides, and a large blue spiral water feature.

7. #209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park
Madison Historic District
10.0 out of 10, Exceptional, (72 reviews)
"The house was clean, comfortable, and had everything we needed. The location was great; very close to restaurants and shops on Main Street as well as the parks by the river. "
United States
Hannah M.
$452 nightly
The price is $532
Oct 4 - Oct 5
Total with taxes and fees
#209 Kings, River View, Deck, Bicentennial Park
A covered porch with a wooden door, potted plants, and a metal railing.

8. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (40 reviews)
"Very nice house and convenient to downtown, etc. If you stay here you definitely won’t be disappointed."
United States
Shirley L.
$229 nightly
The price is $258
Oct 25 - Oct 26
Total with taxes and fees
The Artist’s A-Frame
An aerial view of a swimming pool complex with multiple water slides and a surrounding area with lounge chairs and umbrellas.

9. #207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown
Madison Historic District
10.0 out of 10, Exceptional, (46 reviews)
"Loved this place, very clean and well stocked with the little extras that you always seem to need. "
United States
Matt C.
$424 nightly
The price is $499
Oct 4 - Oct 5
Total with taxes and fees
#207 King Suites, River Views, Deck, Downtown
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

10. 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, (50 reviews)
"Had a very nice stay"
United States
Brad P.
$215 nightly
The price is $247
Oct 7 - Oct 8
Total with taxes and fees
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
A rustic cabin with a porch, stone walls, and an American flag.

11. 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, (173 reviews)
"Great host, clean house in a great location. We really enjoyed our stay."
United States
Michael S.
$424 nightly
The price is $479
Oct 5 - Oct 6
Total with taxes and fees
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
A black house with a number '308' above the door, two potted plants, and a brick pathway leading to the entrance.

12. Downtown Riverfront Cottage

Downtown Riverfront Cottage
Madison Historic District
$309 nightly
The price is $355
Oct 5 - Oct 6
Total with taxes and fees
Downtown Riverfront Cottage
An outdoor patio with a hot tub, a fire pit, and string lights.

13. Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16

Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16
Madison Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Great house. Quiet location. Easy walk to main street resturanrs and shops."
United States
christine g.
$691 nightly
The price is $795
Oct 21 - Oct 22
Total with taxes and fees
Madison Manor by the River | Hot Tub, Game Rm | 5 BRs, 4½ Bath, Sleeps 16
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

14. 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.
$112 nightly
The price is $119
Oct 18 - Oct 19
Total with taxes and fees
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.

15. 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, (8 reviews)
"The host was extremely nice and allowed us to get into the loft a little early. The loft was really nice and we enjoyed out stay. "
United States
Judi K.
$160 nightly
The price is $184
Oct 26 - Oct 27
Total with taxes and fees
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Enjoy the stars from the private hot tub while enjoying the firepit

16. Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill

Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Such a cute little place for my husband and I to get away for my birthday weekend! The house was adorable, well stocked for daily needs and very clean! Will definitely stay here again and recommend it to others!! "
United States
Claire S.
Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

17. 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, (76 reviews)
"Love the stay very relaxed"
United States
Steve C.
$203 nightly
The price is $233
Oct 4 - Oct 5
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A house with a large garage, a dock, and a river.

18. 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.
$255 nightly
The price is $288
Oct 5 - Oct 6
Total with taxes and fees
River Retreat
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

19. Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement

Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement
La Grange
10.0 out of 10, Exceptional, (9 reviews)
"Very nice house, spacious, clean and very comfortable. Perfect for our stay to attend a conference in the area. Highly recommend!!"
United States
Jessica B.
$457 nightly
The price is $517
Oct 5 - Oct 6
Total with taxes and fees
Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement
A modern kitchen with white cabinetry, a granite island, stainless steel appliances, and a hanging light fixture.

20. The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Madison Historic District
9.8 out of 10, Exceptional, (29 reviews)
"Great stay and beautiful house. The location was really outstanding and many restaurants, boutiques, and coffee shops were within walking distance. "
United States
Stephanie B.
$546 nightly
The price is $628
Oct 26 - Oct 27
Total with taxes and fees
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
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

HavenPointe Inn & Suites

HavenPointe Inn & Suites

10/10 Excellent
"This is an excellent, well-maintained, family-owned/run motel. Very clean. We will not hesitate to stay here again. It is close to the freeway but farther away than the cluster of chain motels. The neighborhood is walk-able, and a grocery store is a matter of steps away. A+."
Dan 1-night trip
Posted 3 hours ago
HavenPointe Inn & Suites

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 $126 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.

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.