Pet-friendly holiday rentals in Madison County

Historic schoolhouse suite with onsite coffee shop

Enjoy your stay in the Historic Milton Schoolhouse; home of Maeva's Coffee and known as the most haunted school in Alton Illinois. Stunning 3rd floor apartment with full kitchen and open concept living space. Full view of private courtyard from original windows and hardwood floors throughout the school. This is truly a diamond in the rough. Free parking, wifi and on site laundry. Only ten minutes from downtown Alton and the Mississippi river and thirty-five minutes from downtown St. Louis.

Hilltop Ranch Home on 25 acres bathed in starlight

Welcome to our Hilltop Ranch Home! You will find a relaxing getaway for your entire family or several couples. There is 1800 sq ft on the first floor including a master bedroom with ensuite bathroom boasting a jacuzzi tub, a fully stocked kitchen, gas fireplace, and an attached 2-car garage. In the walkout basement, there is a fourth bedroom, full bath and a TV area. A patio adjoining the dining room, a charcoal grill, and full-size hot tub-all perfect for entertaining your whole group.

Suite Adventures (Whole House)

The perfect short term rental for families and/or small groups. The most bang for your buck. Sleeps up to 10, featuring exotic African decor, jacuzzi, video games, VR headsets, Karaoke, modern appliances, sports bar, movie room, fitness center, 3 bedrooms, 2 pullouts, 2 baths, for you and up to 9 guests. Due to damage caused by tornadoes and pool being repaired, there's no backyard access. However there's patio and jacuzzi access. There is also a laundry available for long term stays.

Romantic tiny home w/ hot tub

The ultimate tiny home retreat you’ve been waiting for. This 500 sqft carriage house was built in 1906! Lovingly and meticulously curated for a perfectly romantic stay. You’ll be a short drive from the always fun Fast Eddie’s Bonair or the gorgeous riverside views. Spend the day walking the Great River Road or trying local shops and restaurants. Looking to stay in? Your space has everything you need for a cozy meal in. Put on a record and relax in your private hot tub.

Loft on the Square

NEWLY RENOVATED 150-year-old building on Highland, Illinois iconic town square. This charming space offers a small-town charm but just a short 45-minute drive to St. Louis. Come and relax in this one-of-a-kind space that is walking distance to many local restaurants, shops, and bars. Make new memories with family and friends (PET FRIENDLY!) in this beautiful space. This space is not handicap accessible as there are steep steps to the second story of this building.

Aunt M's Place

The whole group will enjoy easy access to everything from this centrally-located home. There's plenty to see and do in the Riverbend area of Illinois. This home's proximity to the roads along the Mississippi, as well as the short drive to the Clark bridge or Amtrak station, make for easy access to everything the St. Louis area has to offer. The area is a major stopover for many migratory birds and boasts a number of sites for observing the birds during their travels.

Elm Street Escape- Easy Access to Alton & STL

Escape the daily madness and retreat to this perfectly remodeled historic home - situated in the middle of Upper Alton. A truly unique property, this fully updated 1920s colonial home stands out against its surroundings in a way that is both impressive and welcoming. While the 1 Acre oversized lot establishes some separation from the outside world, the central location with easy access to shopping,local colleges, and downtown STL is ideal.

Boho Barn Loft Countryside Getaway

Brand new furnished loft space in barn surrounded by five lovely, peaceful countryside acres. Includes fully functioning kitchen, fast wifi, outdoor area with grill and fire pit, and plenty of free parking. Sleeps up to 6 people comfortably. Situated above an active destination music / recording studio located 45 minutes from St. Louis, 20 minutes from Edwardsville, 5 minutes from gas / convenience store, 15 minutes from grocery store.

Riverview Home w/ Enclosed Porch in Downtown Alton

This restored 1800s home is in the heart of downtown Alton, making it easy to plan your visit. Walking distance to many local restaurants, coffee shops, bars, and shops! We are conveniently located near Your Event Space and Post Commons, making it easy to walk to the wedding you're in or attending! We are just steps away from The Pedestrian Bridge, giving you walking access to The Ampitheater, Farmers Markets, and Argosy Casino.