The 30 Best Holiday Rentals in Midwest

Ranked 1 out of 7,718 in the region, as well as being 1 of 71 for holiday rentals in Cleveland.

• “So comfortable and extras not expected we ended up staying an extra 2 nights!”
• “We love Mike”
• “You have to see it to believe the Over the Top service and...”
• See more reviews of Family Friendly JUST LIKE HOME

Ranked 2 out of 7,718 in the region, as well as being 1 of 264 for holiday rentals in Chicago.

• “”
• “The flat is prestine clean and really cosy.”
• “A fabulous home located walking distance from the amazing food in little Italy.”
• See more reviews of 1F Cozy Home in Little Italy near Downtown West Loop United Center

Ranked 3 out of 7,718 in the region, as well as being 1 of 5 for holiday rentals in Le Claire.

• “Awesome location and massive suites we will be going back again”
• “Overall our one night stay was great and Chelsea was very nice and helpful.”
• “Great place with a view!”
• See more reviews of River View Lodge

Ranked 4 out of 7,718 in the region, as well as being 1 of 225 for holiday rentals in Branson.

• “”
• “Everything was perfect!”
• “Our daughter ”
• See more reviews of Lizzy's Landing

Ranked 5 out of 7,718 in the region, as well as being 2 of 264 for holiday rentals in Chicago.

• “Would stay here again!”
• “”
• “The place was exactly like the photos the beds were...”
• See more reviews of Chicago Charm

Ranked 6 out of 7,718 in the region, as well as being 1 of 107 for holiday rentals in Milwaukee.

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• “A host that pays attention to the small details”
• See more reviews of The Bentley Condotel, Heart of Walkers Point with Garage, Yard

Ranked 7 out of 7,718 in the region, as well as being 2 of 225 for holiday rentals in Branson.

• “The location and the size and amenities.”
• “It was really nice.”
• “Definitely will stay here again. Would highly recommend.”
• See more reviews of Luxury Condos at Thousand Hills - Heart of Branson - Beautifully remodeled - Spacious and Affordable

Ranked 8 out of 7,718 in the region, as well as being 1 of 13 for holiday rentals in Bay City.

• “”
• “Great location , nice apartment in the middle of it all”
• “”
• See more reviews of Tanner Building

Ranked 9 out of 7,718 in the region, as well as being 2 of 71 for holiday rentals in Cleveland.

• “”
• “Nice Apartment”
• “Comforts of home and space to move around made the stay enjoyable.”
• See more reviews of Cozy house near Lake Erie, 10 minutes to Downtown.

Ranked 10 out of 7,718 in the region, as well as being 3 of 264 for holiday rentals in Chicago.

• “4 real bedrooms and 2 full bathrooms”
• “Cozy family home in a great location”
• “Clean, efficient, excellent host.”
• See more reviews of Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find

Ranked 11 out of 7,718 in the region, as well as being 1 of 20 for holiday rentals in Berlin.

• “”
• “It was really nice!”
• “”
• See more reviews of Barnwood Suite - Main Street Lodge in Berlin

Ranked 12 out of 7,718 in the region, as well as being 1 of 44 for holiday rentals in Columbus.

• “The property exceeded our expectations.”
• “Outstanding value and experience”
• “Wonderful stress free stay.”
• See more reviews of The Cranbrook- Close to OSU-Downtown Columbus-Short North-Clintonville-Upper Arlington

Ranked 13 out of 7,718 in the region, as well as being 1 of 1 for holiday rentals in Riverton.

• “Loved Route 66 vibe, plenty of room, balcony for morning coffee and great back yard.”
• “It was a very enjoyable stay that met all my needs at a reasonable price. The accommodations were qu”
• “”
• See more reviews of The Old Riverton Post on Route 66

Ranked 14 out of 7,718 in the region, as well as being 2 of 2 for holiday rentals in Dresden.

• “Host stopped by to make sure everything was good, he stopped again when I had to ask him to show us how to work the TV 😂”
• “Peaceful”
• “We really enjoyed the quiet and peaceful atmosphere.”
• See more reviews of Martin's River Cabin

Ranked 15 out of 7,718 in the region, as well as being 4 of 264 for holiday rentals in Chicago.

• “”
• “”
• “Beautiful property, well maintained and stocked in a great neighbourhood.”
• See more reviews of 2F Chicago's Little Italy near West Loop & Downtown

Ranked 16 out of 7,718 in the region, as well as being 3 of 115 for holiday rentals in Cincinnati.

• “Very convenient, well equipped, friendly owner”
• “Met up with cousins from neighboring states.relaxing lounging Went out one night.in one nght Lots of great food choic”
• “Place”
• See more reviews of Spacious 2 bed 2 bath Downtown OTR condo minutes walk to the Reds Bengals stadium & more!

Ranked 17 out of 7,718 in the region, as well as being 1 of 30 for holiday rentals in Louisville.

• “”
• “I loved the space.”
• “Cute neighborhood; host was very friendly and offered a lot of food and locations to visit.”
• See more reviews of The B

Ranked 18 out of 7,718 in the region, as well as being 3 of 71 for holiday rentals in Cleveland.

• “The staff was exceptionally friendly and helpful.”
• “Very clean and we enjoyed the atmosphere of the property”
• “Beautiful apartment”
• See more reviews of ROOST Cleveland

Ranked 19 out of 7,718 in the region, as well as being 1 of 2 for holiday rentals in Richmond.

• “Loved it!”
• “Second stay. Will be back. Love this place. Nice weekend getaway.”
• “We were very impressed! We will be back!”
• See more reviews of Richmond No. 267

Ranked 20 out of 7,718 in the region, as well as being 1 of 117 for holiday rentals in Indianapolis.

• “Spacious and Spoiled”
• “The setting was beautiful and Bev was very sweet.”
• “Nice place to stay for gencon”
• See more reviews of Luxury on the lake

Ranked 21 out of 7,718 in the region, as well as being 1 of 34 for holiday rentals in Osage Beach.

• “The stairs were alot .”
• “”
• “We're coming back!”
• See more reviews of F Lakefront! Remodeled, Sleeps 4, Boat Slip, Patio, WiFi, Cable, Pool

Ranked 22 out of 7,718 in the region, as well as being 1 of 46 for holiday rentals in Logan.

• “Absolutely lovely comfortable getaway cabin. I loved it.”
• “An enjoyable stay, very relaxing.”
• “quick getaway”
• See more reviews of Acorn Cottage at Hocking Vacations

Ranked 23 out of 7,718 in the region, as well as being 4 of 115 for holiday rentals in Cincinnati.

• “”
• “”
• “Furniture was comfortable and temperature nice inside”
• See more reviews of The Historic Lyric Penthouse with Private Rooftop

Ranked 24 out of 7,718 in the region, as well as being 1 of 4 for holiday rentals in Hamilton.

• “Great location. Great apartment. Great hosts.”
• “Hassle free comfortable stay with an amazing host. Perfect place to stay if you're in Cincinnati.”
• “Great accomodations and thoughtful host”
• See more reviews of Robin's Nest - Miami U, Weddings or Spooky Nook!

Ranked 25 out of 7,718 in the region, as well as being 3 of 225 for holiday rentals in Branson.

• “Great location and excellent accommodations!”
• “Will be going back”
• “Really enjoyed our stay”
• See more reviews of Penthouse suite at Holiday Hills Book today

Ranked 26 out of 7,718 in the region, as well as being 5 of 115 for holiday rentals in Cincinnati.

• “Stop scrolling. This is the one. Property and host are truly first class. Spotless & comfortable!”
• “Marilyn Monroe”
• “Loved it!”
• See more reviews of *New* XquisiteMidCenturyM0d~ Condo *OTR* w/Parking

Ranked 27 out of 7,718 in the region, as well as being 4 of 225 for holiday rentals in Branson.

• “”
• “The peace and quiet was the best.”
• “”
• See more reviews of Free Daily Attractions including Silver Dollar City! Spacious, Centrally located, 2 pools

Ranked 28 out of 7,718 in the region, as well as being 2 of 64 for holiday rentals in Grand Rapids.

• “”
• “This host takes the cake for VRBO hospitality.”
• “Supplied with everything you need.”
• See more reviews of Cozy Cape Cod

Ranked 29 out of 7,718 in the region, as well as being 5 of 264 for holiday rentals in Chicago.

• “A really nice and clean property in a great location!”
• “I enjoyed my stay and I wish I could stay longer but they are always fully booked.”
• “Excellent apartment.”
• See more reviews of Pulaski Point Properties

Ranked 30 out of 7,718 in the region, as well as being 5 of 225 for holiday rentals in Branson.

• “”
• “It was clean and lived the scripture versus everywhere.”
• “Enjoyed our stay and would stay again”
• See more reviews of 3 Mi to Branson Landing Family Condo with Pool!