Madison Holiday Rentals

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Holiday Rentals in Madison

Mountain Heaven, beautiful mountains. Bearwallow trail is Chapmanville connector

9.6 out of 10, Exceptional, (4)
"Chasing the Hatfields and McCoys. We had fun."
The price is AU$248
includes taxes & fees
1 Dec - 2 Dec
Mountain Heaven, beautiful mountains. Bearwallow trail is Chapmanville connector

Cabin Hatfield McCoy Ivy Branch

10.0 out of 10, Exceptional, (9)
"Absolutely perfect! We stay at short term rentals on a regular basis and this was by far our favorite! Can’t wait to return!"
Cabin Hatfield McCoy Ivy Branch

Discover Tranquility near the Ivy Branch Trails

2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was absolutely perfect for our 2 day dualsport motorcycle adventure. It was super close to lots of fun trails and backroads. We will definitely be coming back next year!"
Discover Tranquility near the Ivy Branch Trails

Firehouse Bandits Houses

10.0 out of 10, Exceptional, (11)
"It was nice being able to ride our atv directly from the house to the trailhead. The house was very clean and nicely maintained."
Firehouse Bandits Houses

Stephen’sHouse Bandits Houses LLC

10.0 out of 10, Exceptional, (14)
"Wonderful place to stay!! The best place we have stayed at so far! The owners are so thoughtful you feel like you are home. The house was so clean and comfy and the owners were so sweet and helpful!"
Stephen’sHouse Bandits Houses LLC

Luxurious cabin, 6 mi HM trails, 12 mi Charleston

10.0 out of 10, Exceptional, (13)
"This was a very nice cabin! We enjoyed our time there. Cozy and comfortable! "
The price is AU$407
includes taxes & fees
26 Nov - 27 Nov
Luxurious cabin, 6 mi HM trails, 12 mi Charleston

Adventure Awaits in a 2 Bedroom apartment in Logan WV. Hatfield McCoy or Hunting

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great property, recently renovated and very clean. The host was very easy to communicate with and super helpful. Location was just a short ride to the Bearwallow trails. Would recommend!"
Adventure Awaits in a 2 Bedroom apartment in Logan WV. Hatfield McCoy or Hunting

Stay in a nice cozy home in the heart of the Hatfield Mccoy Trails!

9.0 out of 10, Wonderful, (2)
"We had a blast. Will hopefully stay at this place again."
Stay in a nice cozy home in the heart of the Hatfield Mccoy Trails!

Cozy house, 2 bed, 1 bath, full kitchen, close to Bearwallow

10.0 out of 10, Exceptional, (28)
"Our trip was great! The house felt like our home away from home. They had everything we could’ve needed! It was a great home base for riding the Bearwallow trails. The road up to the house is a little narrow but no issues if you take your time. Most people are nice and move over as far as they can. Everyone was very friendly and we had some good conversations. Owners were there if we needed them but otherwise we had the house to ourselves. We appreciated the stocked kitchen with plates,...
Cozy house, 2 bed, 1 bath, full kitchen, close to Bearwallow

Riverview Retreat Apartment, minutes to Hatfield and McCoy Trails, State Park

10.0 out of 10, Exceptional, (3)
"Needed a local place to stay for a family reunion. Very clean and conveniently located."
The price is AU$245
includes taxes & fees
26 Nov - 27 Nov
Riverview Retreat Apartment, minutes to Hatfield and McCoy Trails, State Park

Cute Little Whole House For Rent<br>Franklin’s Lodge

9.0 out of 10, Wonderful, (21)
"Our family stayed here for three nights and enjoyed our time. The house is simple and clean and has everything you need! The road it’s on is a little shaky but we never felt unsafe and the neighbor is SO kind and helpful! The kids loved the goats. "
Cute Little Whole House For Rent<br>Franklin’s Lodge

House on Main St., close to restaurants and entertainment. Miles from Trails!

4.0 out of 10, (1)
"The house is very cold. There are 2 units as described but those units only heat 5 ft. in front of it. The living room, kitchen and “second and third bedroom” are unusable. The bedrooms are not bedrooms but just a bed put in a random spot. None of the rooms have doors probably because there is no heat. Parking is a joke. There is a shop next door that details cars and blocks all of the parking. Definitely not worth it. Get a hotel and stay warm! "
The price is AU$560
includes taxes & fees
26 Nov - 27 Nov
House on Main St., close to restaurants and entertainment. Miles from Trails!

Cozy Apartment with onsite restaurant in Logan WV Close to Hatfield McCoy Trail

9.2 out of 10, Wonderful, (5)
"Came in for a family reunion. Host was very welcoming! We enjoyed our stay."
The price is AU$493
includes taxes & fees
8 Dec - 9 Dec
Cozy Apartment with onsite restaurant in Logan WV Close to Hatfield McCoy Trail

Hatfield Mccoy trails, quiet place 3 BR with ATV access - Logan County!

9.6 out of 10, Exceptional, (9)
"Missy and Ben were very quick to answer all of our questions. Ben met us upon our arrival and told us the best ways to get to the trails. The property was just what we needed to make our weekend of riding enjoyable. We would not hesitate to stay here again. Thanks for everything. "
Hatfield Mccoy trails, quiet place 3 BR with ATV access - Logan County!

Gated home nestled in wooded setting- 10 min from Charleston!

10.0 out of 10, Exceptional, (12)
"Excellent!!!"
Gated home nestled in wooded setting- 10 min from Charleston!

The Barn built in 1874

10.0 out of 10, Exceptional, (4)
"Take a walk back in time, along with every conceivable modern convenience at your disposal. Eye candy everywhere you look inside and out. This is a masterpiece, a place to be enjoyed and admired. My congratulations to the owners who turned a barn into a showplace. "
The price is AU$643
includes taxes & fees
26 Nov - 27 Nov
The Barn built in 1874

The Farm - Hatfield McCoy Riders Welcome!, Short Ride to HMT, on 75 Acres, Gated

8.8 out of 10, Excellent, (5)
"Utv riding"
The Farm - Hatfield McCoy Riders Welcome!, Short Ride to HMT, on 75 Acres, Gated

Cozy 3BR home close to trails.

9.4 out of 10, Exceptional, (6)
"Hose was very nice with all the amenities that you would need. Parking was very tight for 3 trucks and trailer hauling side by sides. If 3rd trailer had been the same size as the other 2 all 3 would not have fit with everything off loaded. Other than that it was great. Thanks again"
Cozy 3BR home close to trails.

Cottage 304, 2 Bed w/ Fire Pit, near trails!

10.0 out of 10, Exceptional, (40)
"I've stayed in many VBRO 's and this was the cleanest! Why stay in a noisy hotel when this house is just down the road from BearWallow trails. The host was very kind when we had to leave a day early because of a family emergency. I would 100% stay there again. H house."
Cottage 304, 2 Bed w/ Fire Pit, near trails!

Beautiful Mountain View’s and Located on several acres for privacy

10.0 out of 10, Exceptional, (3)
"My family is originally from Logan, now living in Florida. I rented this house to have a celebration of life for my son. The yard and carport were great for a small gathering with his family and childhood school friends. The fire pit was an added plus as it was pretty nippy after dark on a few nights. Would stay again and highly recommend. Nicely decorated ! "
Beautiful Mountain View’s and Located on several acres for privacy
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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Other types of properties in Madison you may be interested in

Hampton Inn Charleston-Southridge

2.5 star property
9.2 out of 10, Wonderful, (896)
"We enjoyed our stay, everyone was friendly and helpful.Breakfast was amazing."
The price is AU$191
includes taxes & fees
15 Dec - 16 Dec
Hampton Inn Charleston-Southridge

Holiday Inn Express Suites Charleston, an IHG Hotel

2.5 star property
7.4 out of 10, Good, (315)
"The staff was so nice. They allowed our volleyball team to use the conference room to have lunch as a team. "
The price is AU$186
includes taxes & fees
27 Nov - 28 Nov
Holiday Inn Express Suites Charleston, an IHG Hotel

Best Western Logan Inn

2.5 star property
8.4 out of 10, Very good, (373)
"The staff was absolutely amazing!"
The price is AU$159
includes taxes & fees
1 Dec - 2 Dec
Best Western Logan Inn
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Madison has to offer?

Firehouse Bandits Houses: This holiday home rental outside of Madison is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

What can I see and do in Madison?

While you're exploring the area, Chief Logan State Park and Drawdy Falls Roadside Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Bearwallow Hatfield & McCoy Trailhead and Logan County Courthouse.

What are holiday rentals like in Madison?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Madison. Holiday rentals offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for small groups.