Madison County Cottage Rentals & Holiday Homes
Find the best cottages in Madison County - We found 572 exact matches
About Madison County Luxury Rental on Wine Country Villas
Searching for cottages to rent near Madison County? Wine Country Villas features more than 572 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Madison County have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Wine Country Villas’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Madison County.
Are you planning to travel to the lakeside, beach, or mountain area? Wine Country Villas’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Wine Country Villas boasts of 572 holiday cottages and places to stay in Madison County. The site provides unique Airbnb, VRBO, Wine Country Villas-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Madison County Cottage Rentals
What are the top rated Cottage Rentals in Madison County?
There are a lot of options in Madison County. If you plan on staying in the Madison County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Madison County:
- Where beautiful scenery is unavoidable! Fly-fishing, hiking/family time w/pets!
- Trout Fishing Paradise, 10 acres, large yard, creek, private but close to town
- Luxury 5 Bdr/4 Bath Ski in/Ski Out Big Sky Cabin with Hot Tub
- God's beauty abounds! Private log cabin on the Madison River! See Yellowstone!
- Madison River, Mountains, and Relaxation!
- Luxury Home, Ideal Winter Ski-in/Ski-out or Summer Basecamp
- Ski In/Ski out - Great Location in Big Sky Mountain Village
- The Combat Fisherman. Entire house. One block to the Beaverhead. Walk to bars/fo
- Ski-In/Ski-Out Cabin at Powder Ridge – Spacious Family Retreat in Big Sky, MT
- Adventure Awaits! Ski-In/Out Big Sky Townhome by Lake Levinsky & Bear Back Lift
How much does it cost to rent a cottage in Madison County?
The average cost for a cottage rental in Madison County is $627 per night. Winecountryvillas has a wide list of great cottages near Madison County that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Madison County that allow pets?
Yes, here are the top cottage rentals in Madison County that allow you to bring your pet:
- "Front Row" Saddle Ridge - New Bathrooms - Ski-in/out Townhome w/Hot Tub/Views
- Dreamswest Ennis Studio with Deck and Stunning Views
- Sportsmans Lodge
- Immaculate, homey and perfectly located for your stay in downtown Ennis.
See all pet-friendly vacation rentals in Madison County on Winecountryvillas
Do you have any rental cottages in Madison County that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Madison County to find one that works for you.
Are there quality cottages in Madison County that have indoor swimming pools?
As of 2026, the data from Winecountryvillas shows that there are Over 572 private swimming pools or cottages with indoor pools in the Madison County area along with other great amenities.
