Holiday Homes in Middlebury

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Featured Holiday Homes in Middlebury and around

Our top choices for Middlebury holiday homes

includes taxes & fees

10 Sept - 11 Sept

"Beautiful cute cottage.. very clean,everything and anything we could possibly want or need! Plenty of room for our family of 9, and just absolutely perfect and lovely. Great location. Grocery store and cute little ice cream shop within walking distance. Thanks so much!!"

includes taxes & fees

24 Aug - 25 Aug

"Very clean, nicely appointed. Ping pong table and hot tub were a real bonus! "

includes taxes & fees

14 Sept - 15 Sept

Fridge, microwave, oven, coffee/tea maker

"Okay, we came after it had snow a few days prior and nothing was cleared on the many steps nor ramp path, so 6 of us trudged thru snow then tracked snow up wooden stairs that really need some type of padding. NOT for elderly or anyone with steps problems.The 3 beds were so uncomfortable, squeaky and thin; I was able to can feel the mattress quilting through the sheets.The decorative pillow in my bedroom, smelled happily of someone’s cologne.Not impressed at all. Not terrible, but no screens in...

"We stayed just one night and it was lovely. The home was spotless and very cute, and it was decorated so cute. "

includes taxes & fees

2 Sept - 3 Sept

"Beautiful house, well equipped (including an outdoor hot tub!), clean, comfortable, top-notch. We're definitely hoping to stay there again sometime."

includes taxes & fees

10 Sept - 11 Sept

"This is our third time renting this property. The hosts are awesome and pay attention to detail. Couldn't be happier with our stay!"

includes taxes & fees

6 Sept - 7 Sept

"We had a wonderful time here. We stayed here to "unplug" and refresh and it was the perfect place to do so! Comfortable, very clean, with personal touches down to the snacks provided- all made for a stay we will be back for!"

includes taxes & fees

3 Sept - 4 Sept

includes taxes & fees

29 Aug - 30 Aug

"This cottage is beautiful! Super clean, comfortable and decorated perfectly! The lake is so clear! Enjoyed every evening sunset! Loved that we were able to eat and shop in both Middlebury and Shipshewana! We even made a day trip to St Joseph MI. "

"Really peaceful cottage, perfect for a restful break in nature. The birds at the bird feeder and the adorable chickens wandering around really added to the experience. Thank you!"

"The perfect place for us 3, convenient, cozy and a wonderful host. Will reach out if back in the area."

includes taxes & fees

24 Aug - 25 Aug

"The house was very very nice. If You are looking to stay close to a lake that you can walk in, this wouldn’t work. I’m not complaining they are in the process of remodeling but there were things that didn’t work properly. Ants didn’t bother me but they were there in the kitchen. The washer/dryer didn’t work. The price is excellent. But there needs to be repairs and an updated explanation of what is there. I would stay again but I just expected something different when I stayed recently."

"This is a beautiful house. Very clean nice fenced in back yard. Real quiet location. Host is very friendly. We will stay here again if it is available our next trip back."

includes taxes & fees

25 Aug - 26 Aug

"We loved our long weekend getaway! "

includes taxes & fees

5 Sept - 6 Sept

"The Choo Choo Inn was so cozy and comfortable and the host left us a basket of treats waiting for us when we arrived. It was so well appointed with everything we needed and decorated so cute! We’ll definitely look to staying there again when we go back to visit Notre Dame 😊"

"This was a very nice little lake house. We were only there for an overnight stay but would most definitely stay here again anytime we're in this area! Great place!"

includes taxes & fees

27 Aug - 28 Aug