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Chelsea Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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.
$208 nightly
The price is $224
Oct 25 - Oct 26
Total with taxes and fees
Modern cabin very close to scenic riverfront walks
Property grounds

2. 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.
$150 nightly
The price is $173
Nov 2 - Nov 3
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

3. 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.
$115 nightly
The price is $118
Nov 8 - Nov 9
Total with taxes and fees
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
A covered patio with a door, two wicker chairs, and string lights.

4. Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location nice place comfortable "
United States
Hipolito C.
$179 nightly
The price is $200
Oct 24 - Oct 25
Total with taxes and fees
Cozy Tiny House in Scottsburg
A wooden cabin with a porch, a staircase, and a deck.

5. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (17 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
$146 nightly
The price is $163
Nov 9 - Nov 10
Total with taxes and fees
Sassafras Woodland Cabin at Lost Trails
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

6. 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 22 - Oct 23
Total with taxes and fees
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
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7. 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.
$155 nightly
The price is $173
Oct 20 - Oct 21
Total with taxes and fees
Maple Cozy Cabin at Lost Trails
A house with a large garage, a dock, and a river.

8. 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 21 - Oct 22
Total with taxes and fees
River Retreat
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.
$155 nightly
The price is $173
Oct 15 - Oct 16
Total with taxes and fees
Walnut Secluded Cabin at Lost Trails
A cozy room with a bed, a chair, a sofa, and a small table.

10. 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.
$154 nightly
The price is $177
Nov 9 - Nov 10
Total with taxes and fees
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
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, (26 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
United States
Pam
$143 nightly
The price is $162
Oct 20 - Oct 21
Total with taxes and fees
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A log cabin with a fire pit and outdoor seating.

12. 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.
$399 nightly
The price is $431
Nov 4 - Nov 5
Total with taxes and fees
Family-friendly cabin with game room and backyard!
A covered porch with a wooden door, potted plants, and a metal railing.

13. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (41 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.
$230 nightly
The price is $259
Oct 25 - Oct 26
Total with taxes and fees
The Artist’s A-Frame
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

14. 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.
$155 nightly
The price is $173
Oct 21 - Oct 22
Total with taxes and fees
Mulberry Secluded Cabin at Lost Trails
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

15. 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)
"Love the stay very relaxed"
United States
Steve C.
$192 nightly
The price is $220
Oct 20 - Oct 21
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

16. 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.
$165 nightly
The price is $185
Oct 15 - Oct 16
Total with taxes and fees
Cedar Rustic Cabin at Lost Trails
A kitchen with a central island, wooden stools, a trash bin, and a hanging plant arrangement.

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

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Hanover
9.2 out of 10, Wonderful, (7 reviews)
"It was lovely!"
United States
Carolyne R.
$411 nightly
The price is $472
Oct 18 - Oct 19
Total with taxes and fees
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
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.
$200 nightly
The price is $229
Oct 18 - Oct 19
Total with taxes and fees
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
A covered outdoor deck with a table and chairs, a ceiling fan, and a view of a body of water.

19. 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.
$374 nightly
The price is $422
Nov 2 - Nov 3
Total with taxes and fees
T&E Riverhouse Retreat
A room with a bed, two armchairs, a small table, and a microwave.

20. Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
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.
$264 nightly
The price is $308
Oct 29 - Oct 30
Total with taxes and fees
Lakeside Cottage: 1 bed/1 bath
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 was a very clean Hotel. The lobby, breakfast area and meeting room were all very clean. The room looked newly remodeled. I don't know if they were but they were meticulously cleaned. This was an exceptional stay for us and at the price I paid it made it even better. The waffle maker at breakfast made an awesome waffle! Thank You Havenpointe Inn for making us feel so welcome! Jeff M."
Jeff 1-night trip
Posted 1 day 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 $144 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.