Chelsea Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chelsea vacation rentals

Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (5 reviews)
"Was a great space! Clean, modern and very cute! Would highly recommend "
United States
Anna M.
The price is CA $136
CA $236 total
includes taxes & fees
May 6 - May 7
Walnut Secluded Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (9 reviews)
"Very nice place definitely recommend "
United States
Eric T.
Maple Cozy Cabin at Lost Trails

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (30 reviews)
"The place was quiet, well laid out, and exactly as advertised. The snacks and drinks were a nice add-on as well"
United States
Andrew S.
The price is CA $156
CA $319 total
includes taxes & fees
Apr 30 - May 1
The Artist’s A-Frame

Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (11 reviews)
"The amenities were in excellent condition and great layout of the property. "
United States
Ed S.
The price is CA $136
CA $236 total
includes taxes & fees
May 3 - May 4
Sassafras Woodland Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (25 reviews)
"The Rustic Cabin was perfect for our quick visit to the Madison area. The place was comfortable and inviting and tucked away ensuring a quiet and relaxing stay."
United States
Rachel L.
Cedar Rustic Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (2 reviews)
"Mulberry Cabin at Lost Trails was great! The cabin was cozy and felt pretty private (even though the other cabins are within view). The bed was super comfy, and they did a great job making sure the cabin had everything one might need on a trip away from home. It was also very close to all things Madison, so it felt very convenient. We would definitely stay there again!"
United States
Emily I.
The price is CA $137
CA $237 total
includes taxes & fees
May 3 - May 4
Mulberry Secluded Cabin at Lost Trails

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, (8 reviews)
"The host was communicative! The space was clean:) Our pups were cozy! The host sent recommendations as well! Thanks, Laurel! "
United States
Meghan B.
The price is CA $122
CA $235 total
includes taxes & fees
May 10 - May 11
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

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
9.8 out of 10, Exceptional, (41 reviews)
"The property was clean and the host was very responsive prior to and during the stay ensuring a positive trip. "
United States
Natalie H.
The price is CA $158
CA $342 total
includes taxes & fees
May 5 - May 6
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Madison
9.6 out of 10, Exceptional, (21 reviews)
"My wife and I enjoyed our stay here while checking out Madison. Great location, nicely decorated. "
United States
Justin L.
The price is CA $245
CA $393 total
includes taxes & fees
May 1 - May 2
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
10.0 out of 10, Exceptional, (14 reviews)
"Very nice facility and relaxing setting . "
United States
Robert V.
The price is CA $91
CA $229 total
includes taxes & fees
May 5 - May 6
Modern cabin very close to scenic riverfront walks

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, (58 reviews)
"Nice friendly town and eating places"
United States
Paul P.
The price is CA $150
CA $312 total
includes taxes & fees
May 7 - May 8
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

The Madison Inn, Southern view on Main suite 202, Southern view on Main suite 202

The Madison Inn, Southern view on Main suite 202, Southern view on Main suite 202
Madison
9.4 out of 10, Exceptional, (3 reviews)
"The studio was quaint and well appointed. Great location! The host was very accommodating. We look forward to a return stay."
United States
Thomas V.
The Madison Inn, Southern view on Main suite 202, Southern view on Main suite 202

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, (31 reviews)
"Always a wonderful place to stay!"
United States
Leann L.
The price is CA $147
CA $290 total
includes taxes & fees
May 3 - May 4
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

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, (17 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is CA $141
CA $213 total
includes taxes & fees
May 11 - May 12
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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
The price is CA $118
CA $230 total
includes taxes & fees
May 19 - May 20
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Madison
10.0 out of 10, Exceptional, (16 reviews)
"Great location and the host thought of everything to stock the house with."
United States
Kinni L.
The price is CA $188
CA $517 total
includes taxes & fees
May 18 - May 19
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 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.
The price is CA $153
CA $372 total
includes taxes & fees
May 5 - May 6
River Retreat

Peace Cabin- 20 min hike to Wilson Cave!

Peace Cabin- 20 min hike to Wilson Cave!
Deputy
The price is CA $196
CA $310 total
includes taxes & fees
May 6 - May 7
Peace Cabin- 20 min hike to Wilson Cave!

Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (7 reviews)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is CA $164
CA $303 total
includes taxes & fees
May 4 - May 5
Cozy Tiny House in Scottsburg

Country home with beautiful views and access to hiking, biking, and horse trails

Country home with beautiful views and access to hiking, biking, and horse trails
Henryville
10.0 out of 10, Exceptional, (36 reviews)
"Everything was just perfect. Will be staying here again."
United States
Joshua L.
The price is CA $202
CA $343 total
includes taxes & fees
May 6 - May 7
Country home with beautiful views and access to hiking, biking, and horse trails
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chelsea Hotel Reviews

Find out more about Chelsea

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chelsea. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: This vacation home rental near Chelsea offers a patio, a selection of games, and air-conditioning 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 Lanier Mansion.

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.