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Compare 219 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Recently renovated country cottage, 2.5 miles from Shipshewana

10.0 out of 10, Exceptional, (236)
"Exceeded expectations!"
The price is AED 496
AED 728 total
includes taxes & fees
30 Apr - 1 May
Recently renovated country cottage, 2.5 miles from Shipshewana

Live & Love Life on the Lake at Sunset Peak!

10.0 out of 10, Exceptional, (8)
"We loved our long weekend getaway! "
The price is AED 503
AED 1,156 total
includes taxes & fees
6 May - 7 May
Live & Love Life on the Lake at Sunset Peak!

Lake Retreat With Hot Tub

10.0 out of 10, Exceptional, (15)
"This property is wonderful, comfortable and clean. We were delighted, the host was responsive and helpful. Cannot wait to stay again when we can be on the lake."
The price is AED 512
AED 656 total
includes taxes & fees
30 Apr - 1 May
Lake Retreat With Hot Tub

Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

10.0 out of 10, Exceptional, (20)
"Songbird Haven was a perfect place for me and a couple business partners to stay at while in town for a convention at the MEC."
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

Freedom Farm

9.8 out of 10, Exceptional, (32)
"Property and Owner were Perfect!"
Freedom Farm

Kayaks | Relax by River | 10 Min to Shipshewana |

10.0 out of 10, Exceptional, (15)
"Cozey little get away. Clean and updated with a beautiful view. We enjoyed our stay here. "
Kayaks | Relax by River | 10 Min to Shipshewana |

The Cozy Cottage

9.4 out of 10, Exceptional, (6)
"Great house with everything you need. The beds were super comfortable!"
The Cozy Cottage

Cozy Home Retreat

2.0 star property
10.0 out of 10, Exceptional, (8)
"Awesome place, clean, private, and the location is great . We really enjoyed our trip. "
The price is AED 661
AED 1,395 total
includes taxes & fees
30 Apr - 1 May
Cozy Home Retreat

Peaceful lakefront home perfect for families - 2 1/2 hours from Chicago

9.8 out of 10, Exceptional, (76)
"We had our family Christmas get at the house. Big kitchen made meal prep easy. Beautiful swans still swimming in the lake (in December)"
Peaceful lakefront home perfect for families - 2 1/2 hours from Chicago

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (145)
"it was a nice place to stay "
Charming farmhouse in peaceful countryside

The Back Porch Haven Stay in Amish Country yet close to Notre Dame

10.0 out of 10, Exceptional, (15)
"We enjoyed our stay. Very clean and convenient"
The price is AED 514
AED 1,183 total
includes taxes & fees
5 May - 6 May
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

10.0 out of 10, Exceptional, (24)
"I loved this vrbo stay! So clean and nice. "
The price is AED 511
AED 1,362 total
includes taxes & fees
30 Apr - 1 May
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Channel Front Lake Wawasee

9.6 out of 10, Exceptional, (21)
"Great stay, clean, cute chalet great location"
Channel Front Lake Wawasee

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (50)
"Loved the property. Perfect for our family of"older kids". The ping pong table and hot tub got plenty of use! "
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

Summer Sizzle! 6-Bed Channel Home!

9.8 out of 10, Exceptional, (25)
"What a wonderful house! It was well stocked and with two families we had plenty of space. Kids loved it and we plan on returning. Lake Wawasee was beautiful. "
The price is AED 871
AED 2,291 total
includes taxes & fees
30 Apr - 1 May
Summer Sizzle! 6-Bed Channel Home!

Charming, Beautiful 5-bedroom house in wonderful Shipshewana with WiFi, Hot Tub.

2.0 star property
10.0 out of 10, Exceptional, (4)
"This house checks all the boxes!! You won’t find a cleaner, newer or better location! The host is by far the best with communication and the quality of the house is above and beyond amazing! "
Charming, Beautiful 5-bedroom house in wonderful Shipshewana with WiFi, Hot Tub.

Choo Choo Inn

10.0 out of 10, Exceptional, (20)
"We stayed at the Choo Choo Inn while visiting family over Christmas. It was a great spot to stay with our dog and had cute touches all around the rental. We will definitely stay here again when we’re visiting home. "
The price is AED 566
AED 652 total
includes taxes & fees
5 May - 6 May
Choo Choo Inn

Beautiful 6 bedroom lake house with pontoon available for rent

10.0 out of 10, Exceptional, (1)
"We stayed here for Thanksgiving and had a wonderful time celebrating with family. The host is very responsive and helpful, and the home has a gorgeous view, even in cold, snowy November! We would definitely come back!"
Beautiful 6 bedroom lake house with pontoon available for rent

New 4-bedroom house on Lake Wawasee with a stunning, screened in porch!

New 4-bedroom house on Lake Wawasee with a stunning, screened in porch!

Perfect Lake House Getaway

10.0 out of 10, Exceptional, (32)
"This property was amazing. The hosts were very helpful and we had everything we needed. Will be coming back!"
Perfect Lake House Getaway
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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Other property types in Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

2.0 star property
10.0 out of 10, Exceptional, (11)
"Very clean"
The price is AED 422
AED 531 total
includes taxes & fees
30 Apr - 1 May
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

10.0 out of 10, Exceptional, (9)
"The stay was absolutely amazing. The cabin was clean, organized and well stocked with all of our needs. The amenities were well taken care of and fun. It was all around amazing. "
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

The Back Porch Haven Stay in Amish Country yet close to Notre Dame

10.0 out of 10, Exceptional, (15)
"We enjoyed our stay. Very clean and convenient"
The price is AED 514
AED 1,183 total
includes taxes & fees
5 May - 6 May
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
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.