The 30 Best Holiday Rentals in Midwest

Ranked 1 out of 5,467 in the region, as well as being 1 of 86 for holiday rentals in Cleveland.

• “Host is so great! Provided so many extras”
• “The ONLY place to stay in Cleveland!!”
• “Good stay, place just for us.”
• See more reviews of Ecco friendly just like Home

Ranked 2 out of 5,467 in the region, as well as being 1 of 5 for holiday rentals in Lebanon.

• “Everything .”
• “Our hosts were exceptional, the apartment was probably the best anyone could wish for, secure parking spot, host even pr”
• “This place is very well appointed.”
• See more reviews of Guest Apartment at Commercial Street Studio

Ranked 3 out of 5,467 in the region, as well as being 1 of 5 for holiday rentals in Le Claire.

• “One of the most relaxing, comfortable, fun stays we have ever experienced.”
• “Wonderful place to stay for an anniversary”
• “Beautiful, Elegant, excellent facility for an event”
• See more reviews of River View Lodge

Ranked 4 out of 5,467 in the region, as well as being 1 of 156 for holiday rentals in Louisville.

• “NA”
• “A wonderful choice for Louisville visit to avoid the congestion of city life.”
• “Our host was amazingly helpful and gave us great recommendations during our stay. I would go back!”
• See more reviews of The B

Ranked 5 out of 5,467 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 5,467 in the region, as well as being 1 of 137 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 5,467 in the region, as well as being 1 of 12 for holiday rentals in Bay City.

• “Everything!”
• “We 110% rebook next time in town!”
• “Very convenient, we walked to venues, restaurants, arcades,...”
• See more reviews of Tanner Building

Ranked 8 out of 5,467 in the region, as well as being 1 of 44 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 9 out of 5,467 in the region, as well as being 1 of 170 for holiday rentals in Branson.

• “The location was very convenient and we had plenty of room for 2 families to stay.”
• “Perfect”
• “Best place we have stayed in Branson!”
• See more reviews of Luxury Condos at Thousand Hills - Heart of Branson - Beautifully remodeled - Spacious and Affordable

Ranked 10 out of 5,467 in the region, as well as being 1 of 19 for holiday rentals in Berlin.

• “The stay was amazing, the apartment was clean and updated to...”
• “Perfect in every way!”
• “It was great!”
• See more reviews of Barnwood Suite - Main Street Lodge in Berlin

Ranked 11 out of 5,467 in the region, as well as being 2 of 137 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 5,467 in the region, as well as being 2 of 86 for holiday rentals in Cleveland.

• “Love it at the May.”
• “Great place. Look forward to another visit...”
• “Clean”
• See more reviews of ROOST Cleveland

Ranked 13 out of 5,467 in the region, as well as being 3 of 137 for holiday rentals in Chicago.

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

Ranked 14 out of 5,467 in the region, as well as being 5 of 84 for holiday rentals in Cincinnati.

• “The condo was spotless, spacious, and such a great value.”
• “A perfect spot for a short business trip to Cincinnati”
• “Perfect for a group of 4”
• See more reviews of Spacious 2 bed 2 bath Downtown OTR condo minutes walk to the Reds Bengals stadium & more!

Ranked 15 out of 5,467 in the region, as well as being 1 of 55 for holiday rentals in Indianapolis.

• “Perfect!”
• “Pictures don’t do it justice! It was the most perfect getaway for a concert at the Ruoff Center.”
• “This was our last stop before finally heading home from a 10 day road trip out east. We were dead tired and ready to jus”
• See more reviews of Luxury on the lake

Ranked 16 out of 5,467 in the region, as well as being 6 of 84 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 17 out of 5,467 in the region, as well as being 1 of 1 for holiday rentals in Elizabeth.

• “This was my first stay at a B&B & it couldn’t have...”
• “An experience to be recommended and repeated...”
• “Wonderful!”
• See more reviews of Derinda House

Ranked 18 out of 5,467 in the region, as well as being 2 of 170 for holiday rentals in Branson.

• “LOVELY!!!!”
• “Overall good experience”
• “Even thought we made the most out of everything in Branson had our trip was Relaxing and Enjoyable.”
• See more reviews of Lizzy's Landing

Ranked 19 out of 5,467 in the region, as well as being 7 of 84 for holiday rentals in Cincinnati.

• “Exceptional loft beautiful kitchen. Perfect for entertaining friends and family. fa”
• “Overall stay was great and we will definitely be back!”
• “The location and the aesthetic was great.”
• See more reviews of The Historic Lyric Penthouse with Private Rooftop

Ranked 20 out of 5,467 in the region, as well as being 5 of 25 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 21 out of 5,467 in the region, as well as being 4 of 137 for holiday rentals in Chicago.

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

Ranked 22 out of 5,467 in the region, as well as being 6 of 156 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 23 out of 5,467 in the region, as well as being 5 of 137 for holiday rentals in Chicago.

• “Very cozy place and a nice neighborhood.”
• “The space was perfect for our group.”
• “property managers were very nice and willing to accomodate our soecial request to enter property earlier than check in t”
• See more reviews of The Avondale Guesthouse

Ranked 24 out of 5,467 in the region, as well as being 1 of 1 for holiday rentals in Riverton.

• “A neat stop on the way to Crystal Bridges”
• “It gave an at home feel while traveling.”
• “Very cute but not a B&B”
• See more reviews of The Old Riverton Post on Route 66

Ranked 25 out of 5,467 in the region, as well as being 1 of 27 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 5,467 in the region, as well as being 3 of 170 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 27 out of 5,467 in the region, as well as being 2 of 27 for holiday rentals in Columbus.

• “A lovely weekend in a cute house.”
• “The porch and had everything you need”
• “A very comfy home away from home!”
• See more reviews of Chic 2BR near DT, 8 min walk to Park&Conservatory

Ranked 28 out of 5,467 in the region, as well as being 6 of 137 for holiday rentals in Chicago.

• “Lovely and peaceful location”
• “The host was very nice, the rooms were cleanly and the area...”
• “Great Stay!”
• See more reviews of Forrestville Ave Large Suite

Ranked 29 out of 5,467 in the region, as well as being 2 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

Ranked 30 out of 5,467 in the region, as well as being 3 of 35 for holiday rentals in Duluth.

• “I would stay here again.”
• “Enjoyed it!”
• “The facilities were new, clean, comfortable, and quiet.”
• See more reviews of Lincoln Park Boutique Hotel