The 30 Best Holiday Rentals in Midwest

Ranked 1 out of 5,403 in the region, as well as being 1 of 71 for holiday rentals in Cleveland.

• “Good stay, place just for us.”
• “Clean, accommodating and kitchen fully equipped and lots of...”
• “Our one night stay of " Family Goodness and Blessings "”
• See more reviews of Ecco friendly just like Home

Ranked 2 out of 5,403 in the region, as well as being 1 of 148 for holiday rentals in Louisville.

• “Awesome - couldn’t be any better”
• “Clean, comfortable, inexpensive, great location, great host...”
• “Great location, but too many unfinished projects to be renting out, especially without mentioning.”
• See more reviews of The B

Ranked 3 out of 5,403 in the region, as well as being 1 of 5 for holiday rentals in Lebanon.

• “This place is very well appointed.”
• “The apartment had two bedrooms and two baths were clean and just what we were looking for.”
• “Wonderful, spacious well-appointed apartment.”
• See more reviews of Guest Apartment at Commercial Street Studio

Ranked 4 out of 5,403 in the region, as well as being 1 of 4 for holiday rentals in Le Claire.

• “Beautiful, Elegant, excellent facility for an event”
• “It was quiet, comfortable, and beautiful.”
• “Such a great location, accommodations and easy place to stay.”
• See more reviews of River View Lodge

Ranked 5 out of 5,403 in the region, as well as being 1 of 5 for holiday rentals in Milford.

• “Perfect for a couple looking to enjoy all the dining and libations downtown Milford has to offer!”
• “A bargain apt in a great location in Milford, Ohio.”
• “A perfect blend of comfort and convenience.”
• See more reviews of The Estate Loft in Downtown Milford

Ranked 6 out of 5,403 in the region, as well as being 1 of 185 for holiday rentals in Chicago.

• “Great property and well worth the value, so much room and...”
• “I love this place! Great location, friendly hosts, lovely decor, and a dedicated parking spot. 10/10”
• “The best reasonable mansion near Chicago downton”
• See more reviews of 1F Cozy Home in Little Italy near Downtown West Loop United Center

Ranked 7 out of 5,403 in the region, as well as being 1 of 42 for holiday rentals in Des Moines.

• “The heated bathroom floor was phenomenal!”
• “Very nice facilities, cool aesthetic, comfortable, and private.”
• “This is a hidden gem in downtown Des Moines. We liked it much better than a hotel..”
• See more reviews of Historical Oscar Lofquist house in the heart of Des Moines

Ranked 8 out of 5,403 in the region, as well as being 1 of 19 for holiday rentals in Berlin.

• “It was great!”
• “The room was beautiful.”
• “Very nice, clean, loved the room!”
• See more reviews of Barnwood Suite - Main Street Lodge in Berlin

Ranked 9 out of 5,403 in the region, as well as being 1 of 164 for holiday rentals in Branson.

• “Lots of room for 6 of us.”
• “We had a nice comfortable day.”
• “Had a perfect time in this spotless clean condo. We will be back!”
• See more reviews of Luxury Condos at Thousand Hills - Heart of Branson - Beautifully remodeled - Spacious and Affordable

Ranked 10 out of 5,403 in the region, as well as being 2 of 71 for holiday rentals in Cleveland.

• “2 bedroom apartment was very spacious and comfortable and...”
• “The apartment was very spacious, clean and comfortable beds!”
• “Very nice, modern accommodations in Downtown Cleveland”
• See more reviews of ROOST Cleveland

Ranked 11 out of 5,403 in the region, as well as being 2 of 185 for holiday rentals in Chicago.

• “Excellent Chicago Choice”
• “Harika”
• “Perfect townhome in the lakeshore community area of Chicago. Convenient to everything!”
• See more reviews of Chicago Charm

Ranked 12 out of 5,403 in the region, as well as being 3 of 185 for holiday rentals in Chicago.

• “This was the perfect place to relax after a long day exploring Chicago.”
• “Great option for multiple guests very close to Wrigley Field.”
• “Great location.”
• See more reviews of Wrigley Oasis! Steps from the Field! - 3BD 1BA

Ranked 13 out of 5,403 in the region, as well as being 5 of 80 for holiday rentals in Cincinnati.

• “Great location, nice personal touches.”
• “The location is great, the owners responded quickly to...”
• “The decor was fresh and modern.”
• See more reviews of **NEW mOdernLUX best OTR condo *Park ONsite**

Ranked 14 out of 5,403 in the region, as well as being 4 of 185 for holiday rentals in Chicago.

• “Great place - would come again!”
• “Fantastic place to stay. 100% satisfied”
• “Perfect short stay”
• See more reviews of 2F Chicago's Little Italy near West Loop & Downtown

Ranked 15 out of 5,403 in the region, as well as being 4 of 27 for holiday rentals in Millersburg.

• “This quiet Qant little cabin provides peace,tranquility and a quick getaway from the city It’s A Must Stay!”
• “A recliner:)”
• “The stay was pleasant and the cabin was very clean just know to bring some grilling things with you if you intend to gri”
• See more reviews of The Cayo Cabin, Millersburg Ohio

Ranked 16 out of 5,403 in the region, as well as being 2 of 164 for holiday rentals in Branson.

• “Even thought we made the most out of everything in Branson had our trip was Relaxing and Enjoyable.”
• “It had all the convenience of home.”
• “Very clean and comfortable.”
• See more reviews of Lizzy's Landing

Ranked 17 out of 5,403 in the region, as well as being 1 of 47 for holiday rentals in Indianapolis.

• “Beautiful place, nice location.”
• “Host are wonderful. Although I didn’t meet Bev. Dan is a class act. I plan to return.”
• “Breathtaking property, fantastic hosts!”
• See more reviews of Luxury on the lake

Ranked 18 out of 5,403 in the region, as well as being 6 of 80 for holiday rentals in Cincinnati.

• “A perfect spot for a short business trip to Cincinnati”
• “Perfect for a group of 4”
• “Great place to stay”
• See more reviews of Spacious 2 bed 2 bath Downtown OTR condo minutes walk to the Reds Bengals stadium & more!

Ranked 19 out of 5,403 in the region, as well as being 1 of 1 for holiday rentals in Elizabeth.

• “An experience to be recommended and repeated...”
• “Wonderful!”
• “place was nice the food was good and the host was very nice”
• See more reviews of Derinda House

Ranked 20 out of 5,403 in the region, as well as being 6 of 148 for holiday rentals in Louisville.

• “Everything but parking”
• “Clean and quaint!”
• “Great home in a great location”
• See more reviews of Lux Townhouse, Walk to All, Sleeps 6 Adults

Ranked 21 out of 5,403 in the region, as well as being 5 of 185 for holiday rentals in Chicago.

• “Wonderful stay”
• “The size of the apartment was large.”
• “Very quiet and comfortable. Loved the decor! Comfortable beds.”
• See more reviews of The Avondale Guesthouse

Ranked 22 out of 5,403 in the region, as well as being 3 of 164 for holiday rentals in Branson.

• “The view was amazing!”
• “Great stay with a beautiful view of the mountains and lake. Would 1000% recommend it.”
• “We will definitely be returning costumers!”
• See more reviews of Penthouse w Lake View & private deck- next to SDC

Ranked 23 out of 5,403 in the region, as well as being 1 of 1 for holiday rentals in Riverton.

• “Was a great experience to stay here, would stay again.”
• “5 star property”
• “Unique stay on Route 66 in a well appointed apartment!”
• See more reviews of The Old Riverton Post B&B

Ranked 24 out of 5,403 in the region, as well as being 7 of 80 for holiday rentals in Cincinnati.

• “Overall stay was great and we will definitely be back!”
• “The location and the aesthetic was great.”
• “Amazing loft space.”
• See more reviews of The Historic Lyric Penthouse with Private Rooftop

Ranked 25 out of 5,403 in the region, as well as being 3 of 153 for holiday rentals in Columbus.

• “We will be back!”
• “Our stay was wonderful!”
• “Overall 9.5”
• See more reviews of Modern Boho Stylish 1BR Near DT on Historic Street

Ranked 26 out of 5,403 in the region, as well as being 4 of 153 for holiday rentals in Columbus.

• “The porch and had everything you need”
• “A very comfy home away from home!”
• “Beautiful calm place to getaway.”
• See more reviews of Chic 2BR near DT, 8 min walk to Park&Conservatory

Ranked 27 out of 5,403 in the region, as well as being 6 of 185 for holiday rentals in Chicago.

• “The host was very nice, the rooms were cleanly and the area...”
• “Great Stay!”
• “A quiet, clean, comfortable stay!”
• See more reviews of Forrestville Ave Large Suite

Ranked 28 out of 5,403 in the region, as well as being 4 of 164 for holiday rentals in Branson.

• “The cottage fits our family very well and is within walking...”
• “We had a relaxing stay at the cozy cottage.”
• “Wonderful stay.”
• See more reviews of Cozy Lakefront Cottage Getaway Branson MO.

Ranked 29 out of 5,403 in the region, as well as being 5 of 83 for holiday rentals in Milwaukee.

• “The unit was perfectly located next to Fiserv stadium for us to attend our daughter's graduation.”
• “I will travel again and use this property. I will also recommend this property to others”
• “It was clean.”
• See more reviews of Flexhome Skywalk to Fiserv 1BR Apt U5 - READ INFO

Ranked 30 out of 5,403 in the region, as well as being 3 of 32 for holiday rentals in Bloomington.

• “Everything & especially the decorating.”
• “Great host and accommodations!”
• “fun enjoyable and more than worth the value”
• See more reviews of Boho-Chic Travel Pad - Unit 2