Top Cottages in Madison County in 2026

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Top Cities in Madison County

A historic downtown sign with a building illustration and founding year.

Our top choices for Madison County cottages

A modern house with a deck, large windows, and a pathway leading to the entrance.

1. Wooded Oasis.Free Bottle of Wine+Breakfast+Golf

Caseyville

amy m.

AED 761 total

includes taxes & fees

21 Oct - 22 Oct

A brick house with a front porch, a mailbox, and a small garden.

2. Historic headquarters of city founder! Gated parking!

St. Charles Historic District

Judith H.

A two-story building with a balcony, a staircase, and a well-lit entrance.

3. 1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

St. Charles Historic District

julie e.

A covered outdoor seating area with a table and chairs, overlooking a grassy field and a body of water.

4. Charming 2-bedroom cottage with WiFi and AC in serene Grafton

Grafton

Trisha B.

5. Main Street Cottage with Hot Tub

Grafton

Ian P.

AED 1,153 total

includes taxes & fees

15 Oct - 16 Oct

A hot tub under a wooden pergola with a view of a lake and trees.

6. Lakefront Family Home 13 Mi From Gateway Arch!

Granite City

A two-story house with a garage, a front porch, and a small front yard.

7. Route 66 Gem! Charming Litchfield Home w/ Yard

Litchfield

A single-story brick house with a front porch, a visible chimney, and a driveway leading to the front door.

8. Delightful Cottage by Clayton

University City

Joe R.

A house with a front porch, a set of steps leading to the door, and a wooden fence in the background.

9. Walk to Tower Grove Park: St Louis Getaway

Tower Grove South

Jared

A two-story house with a front porch, a brick chimney, and a white picket fence.

10. Lakeside Clifton Heights Home Near Forest Park

Clifton Heights

A row of three-story townhouses with front porches, a small garden area, and a metal fence.

11. Home 2 Mi to Dtwn St Louis: Great for Families!

Lafayette Square

Kelsey

A residential area with houses, a covered driveway, and a lawn.

12. 12 Mi to St Louis: Pet-friendly Metro East Home

Granite City

"This is the worst VRBO our family has ever stayed at. Host changed the duplex a couple of hours before our arrival. The new unit was uncleaned with some linens still wet in the washing machine. It had a room that had no light, old moldy food, cabinets without fronts, windows without coverings, a screen door ripped off, & beds that were very nasty and stained. Garbage wasn’t taken out from the last guest. They only provided 3 towels (that need to be washed) when we reserved for 6. Host absolutely...

Christopher

A two-story house with a covered porch and a staircase leading to the second floor.

13. Saint Charles House Near Historic Downtown!

St. Charles

A two-story building with a brick facade and a covered porch.

14. 'hidden Paradise' on 5 Acres w/ Hot Tub & Deck!

Florissant

"Beautiful well kept secret in a very peaceful setting: we had a large family Thanksgiving week in this beautiful place. There was more than enough rooms for four families to come together and still have enough room for dining visitors. It is beyond well equipped and you should contact the owner before you bring unnecessary items. Great hot tub. Spacious and well equipped baths and showers with all personal supplies and plush towels. Beds were all amazing. There is a great playroom...

Kim

A two-story house with a red front door, a driveway, and a lawn.

15. St Louis Home < 1 Mi to Forest Park!

Dogtown

Marisol

A small white house with a green door and windows, surrounded by trees and a grassy yard.

16. Charming Hillsboro Home < 1 Mi to Downtown!

Hillsboro

Kim a

17. Charming 2-bedroom house facing bike trails in Downtown Glen Carbon

Glen Carbon

A backyard with a wooden fence, a concrete planter, and a small tree.

18. 9 Mi to Dtwn: Vibrant St Louis Home!

St. Louis

A two-story red brick building with a black front door, a small balcony, and a front yard with a wooden fence and a tree.

19. Red Brick Hideaway

Fox Park

A two-story brick house with a front porch, steps, and a small garden with mulch and shrubs.

20. St Louis Vacation Rental 4 Mi to Airport!

Bel-Nor

Shaniel

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Top Madison County Hotel Reviews

Pear Tree Inn St. Louis Airport

8/10 Good

"The property was great but the breakfast menu was the same every morning. I would’ve liked a little more variety. The happy hour cocktails were nice. The room and property were clean. I would’ve liked highly recommend thus property."

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

10/10 Excellent

"This hotel is located in a great location, close to the Gateway Arch and the ballpark where the Cardinals play. There were numerous fun restaurants within walking distance, and we felt safe except down by the Old Spaghetti Factory. I would stay in this hotel again and recommend it to others."

Pear Tree Inn St. Louis Near Union Station

10/10 Excellent

"The property itself was maintained ok. It does need to be updated as the carpets and bathrooms are old. Our ceiling in the bathroom was peeling due to the humidity from the shower over the years. The carpet in the rooms and common areas is older. As for the staff everyone was nice and did what was expected of them. I would use this property again to stay as it’s walking distance from everything downtown."

Clayton Plaza Hotel & Extended Stay

8/10 Good

"Hotel staff were excellent, friendly, professional and by far the best reason to re-book. The hotel itself was very clean, located near professional buildings/courts and some eateries within walking distance. The room was clean as well and nicely proportioned with some of the best mattresses/bedding I've experienced. Only slight downside was the breakfast bar--the food and choices were ample and very good (especially the made to order omelets and waffles) but the setting was less than clean and rather worn--not in keeping with the rest of the hotel. All in all, a great place to stay and would definitely book again."

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Check prices for these dates

Top Cities in Madison County

Troy

Our top choices for Madison County cottages

1. Wooded Oasis.Free Bottle of Wine+Breakfast+Golf

2. Historic headquarters of city founder! Gated parking!

3. 1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

4. Charming 2-bedroom cottage with WiFi and AC in serene Grafton

5. Main Street Cottage with Hot Tub

6. Lakefront Family Home 13 Mi From Gateway Arch!

7. Route 66 Gem! Charming Litchfield Home w/ Yard

8. Delightful Cottage by Clayton

9. Walk to Tower Grove Park: St Louis Getaway

10. Lakeside Clifton Heights Home Near Forest Park

11. Home 2 Mi to Dtwn St Louis: Great for Families!

12. 12 Mi to St Louis: Pet-friendly Metro East Home

13. Saint Charles House Near Historic Downtown!

14. 'hidden Paradise' on 5 Acres w/ Hot Tub & Deck!

15. St Louis Home < 1 Mi to Forest Park!

16. Charming Hillsboro Home < 1 Mi to Downtown!

17. Charming 2-bedroom house facing bike trails in Downtown Glen Carbon

18. 9 Mi to Dtwn: Vibrant St Louis Home!

19. Red Brick Hideaway

20. St Louis Vacation Rental 4 Mi to Airport!

Find vacation rentals that suit your style

Top Madison County Hotel Reviews

Pear Tree Inn St. Louis Airport

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

Courtyard by Marriott St. Louis Downtown/Convention Center

Pear Tree Inn St. Louis Near Union Station

Clayton Plaza Hotel & Extended Stay

Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis Union Station

Moonrise Hotel

Live by Loews - St.Louis

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