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Holiday Rentals in Macoupin County

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Featured Holiday Rentals in Macoupin County

Home is on the original 1926-1930 Route 66 alignment
Stroll through the beautifully maintained garden, surrounded by a variety of flowering plants and lush greenery.

Home is on the original 1926-1930 Route 66 alignment

10.0 out of 10, Exceptional, (89)
"Great Stay with family a couple of blocks away"
The price is €142
includes taxes & fees
5 Aug - 6 Aug
Home is on the original 1926-1930 Route 66 alignment
Lake House off Route 66
Welcome to this charming home, featuring a cozy porch with a decorative glass door and a serene garden area.

Lake House off Route 66

9.0 out of 10, Wonderful, (2)
"The home itself was fantastic—clean, well-maintained, and exactly as pictured. The host was responsive and friendly, and the location right on the lake made for a relaxing stay. The only downside, and the reason I’m giving 4 stars instead of 5, is that there’s a camper in the front yard with people staying in it. This wasn’t disclosed in the listing, and it made the experience feel a bit less private and more awkward than expected. If that had been communicated up front, it would’ve helped set...
The price is €196
includes taxes & fees
2 Aug - 3 Aug
Lake House off Route 66
Luxurious Otter Pointe
Stunning staircase leads to an upper level with a door and wooden paneling.

Luxurious Otter Pointe

10.0 out of 10, Exceptional, (23)
"We loved the open indoor kitchen and living room space for gathering. The kids and adults enjoyed the various games in the gameroom and loft. It was also lovely to sit on the back porch in the morning and evening. Jason’s place is well-stocked and beautiful!"
Luxurious Otter Pointe
HOT TUB! Fishermans lake house retreat
Relax in a hot tub under a shaded pergola, surrounded by a grassy yard and a wooden fence.

HOT TUB! Fishermans lake house retreat

8.0 out of 10, Very good, (8)
The price is €231
includes taxes & fees
11 Aug - 12 Aug
HOT TUB! Fishermans lake house retreat
Grafton Escape #1 - River views! Pool! Walking distance to bars/restaurants
Relax by the pool surrounded by lush trees and a scenic hillside view.

Grafton Escape #1 - River views! Pool! Walking distance to bars/restaurants

9.8 out of 10, Exceptional, (64)
"Property is great loved it"
Grafton Escape #1 - River views! Pool! Walking distance to bars/restaurants
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Cozy dining area with a wooden table and chairs, a patterned rug, and a refrigerator.

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

10.0 out of 10, Exceptional, (9)
"Very nice and cozy cabin in the middle of a cornfield. This place is close to town but completely isolated. We sat on the front porch and enjoyed our morning coffee in almost complete silence. Not sure if this is the place for everyone, but it was perfect for us."
The price is €110
includes taxes & fees
29 Jul - 30 Jul
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Grafton Escape #2 - River views! Pool! Walking distance to bars/restaurants
Relax on the deck with a scenic view of the water and city skyline.

Grafton Escape #2 - River views! Pool! Walking distance to bars/restaurants

10.0 out of 10, Exceptional, (66)
"Perfect location and set up for ourselves and another couple. Michelle is an awesome hoey"
Grafton Escape #2 - River views! Pool! Walking distance to bars/restaurants
Confluence Cabin Grafton, IL
Surrounded by lush greenery, this cabin-style building offers a porch and deck with outdoor lighting.

Confluence Cabin Grafton, IL

9.8 out of 10, Exceptional, (35)
"I’d recommend for a place to stay in Grafton "
Confluence Cabin Grafton, IL
Charming Escape in Grafton!
Relax in this serene sunroom with a view of the lake and grassy field, featuring a sofa, chair, and round table with a plant.

Charming Escape in Grafton!

10.0 out of 10, Exceptional, (9)
"Great location, very nice, clean, with everything you need. I wish the weather would have been a little better. We would definitely stay again. "
Charming Escape in Grafton!
Two bedroom, 2 1/2 bath Condo. Great River Views & Pool!
Enjoy cooking in this well-equipped kitchen with a sink, dishwasher, microwave, and ample counter space.

Two bedroom, 2 1/2 bath Condo. Great River Views & Pool!

9.8 out of 10, Exceptional, (164)
"Property was nice and location was terrific. "
Two bedroom, 2 1/2 bath Condo. Great River Views & Pool!
Riverside Home - Modern meets comfort
Relax in this stylish living room with a sofa, armchair, and flat-screen TV.

Riverside Home - Modern meets comfort

10.0 out of 10, Exceptional, (52)
"Great property for a quick stay."
The price is €259
includes taxes & fees
29 Jul - 30 Jul
Riverside Home - Modern meets comfort
Charming Edwardsville Home: Walk to Downtown!
Welcome to Rollo, a charming home with a cozy porch and lush garden.

Charming Edwardsville Home: Walk to Downtown!

9.8 out of 10, Exceptional, (20)
"We very much enjoyed our stay at this adorable property. Very well furnished everything you need and we even had a special treat of delicious cinnamon rolls left for us on the kitchen counter. If we are ever in the area again we would definitely stay here. "
Charming Edwardsville Home: Walk to Downtown!
Guest House 632 Summit Street
Situated on a street corner, this two-story house features a balcony on the upper level.

Guest House 632 Summit Street

10.0 out of 10, Exceptional, (185)
"I am very thankful for the opportunity to stay in this beautiful home in a beautiful area. I truly enjoyed my visit with the nearby parks and views of the water and surrounding area. I would enjoy staying here again!"
Guest House 632 Summit Street
Cozy Renovated Bungalow Perfect for Families
Enjoy cooking in this well-equipped kitchen with a central island, stove, and ample storage.

Cozy Renovated Bungalow Perfect for Families

9.6 out of 10, Exceptional, (9)
"Great place"
Cozy Renovated Bungalow Perfect for Families
The River Stables in St. Charles, MO
Relax on the deck with a serene view of the lake surrounded by lush greenery.

The River Stables in St. Charles, MO

2.0 star property
9.6 out of 10, Exceptional, (10)
"So nice to relax and not worry, So much better than a hotel and safe and an escape from St Louis Highly recommended"
The River Stables in St. Charles, MO
Charming 2-bedroom cottage with WiFi and AC in serene Grafton
Relax in this stylish living space with a leather sofa, dining area, and fully equipped kitchen.

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

9.2 out of 10, Wonderful, (15)
"The location was perfect snd the view was amazing! Will stay here again!!"
Charming 2-bedroom cottage with WiFi and AC in serene Grafton
Charming upper level of 3-bedroom house in Grafton, IL
Enjoy cooking in this well-equipped kitchen with a black stove, sink, and coffee bar.

Charming upper level of 3-bedroom house in Grafton, IL

10.0 out of 10, Exceptional, (1)
"The stay was phenomenal. The location was a block away from everything. Restaurants, bars, shops, and gas stations were accessible within a rock’s throw. The host was there if I needed her. The house was perfect for me and my group. Everyone was very impressed."
The price is €500
includes taxes & fees
29 Jul - 30 Jul
Charming upper level of 3-bedroom house in Grafton, IL
Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks
Cozy cabin nestled among trees, offering a peaceful retreat with a porch and large windows.

Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks

9.4 out of 10, Exceptional, (9)
"Very relaxing fun place to stay!"
The price is €326
includes taxes & fees
30 Jul - 31 Jul
Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks
Rafton Inn Vacation Cottage 93
Enjoy a relaxing stay in this charming home with a front porch, perfect for unwinding with a cup of coffee or a good book.

Rafton Inn Vacation Cottage 93

9.4 out of 10, Exceptional, (3)
"Easy to find. Very clean. Fun place to stay "
The price is €276
includes taxes & fees
29 Jul - 30 Jul
Rafton Inn Vacation Cottage 93
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
Kitchen area with a stainless steel sink, dishwasher, and ample countertop space.

Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees

10.0 out of 10, Exceptional, (24)
"We had a great stay. The environment is just cuddling. "
The price is €108
includes taxes & fees
5 Aug - 6 Aug
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
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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Top Macoupin County Hotel Reviews

Crowne Plaza Springfield by IHG

Crowne Plaza Springfield by IHG

10/10 Excellent
"Property was nice around pool areas need chairs outside"
Ida 2-night trip
Posted 15 hours ago
Crowne Plaza Springfield by IHG