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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 206 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Recently renovated country cottage, 2.5 miles from Shipshewana
Exterior

Recently renovated country cottage, 2.5 miles from Shipshewana

10.0 out of 10, Exceptional, (233)
"Great place for a getaway. Close to shops in Shipshewana, but far enough away to avoid busyness. Would definitely stay again. House was cozy and comfortable. "
The price is AED 496
AED 720 total
includes taxes & fees
26 Mar - 27 Mar
Recently renovated country cottage, 2.5 miles from Shipshewana
Live & Love Life on the Lake at Sunset Peak!
Miscellaneous

Live & Love Life on the Lake at Sunset Peak!

10.0 out of 10, Exceptional, (4)
"Absolutely beautiful home that was cozy yet quite spacious. It would be good for a larger group and a longer stay as there is quite a lot of space… Both in the kitchen area as well as gathering spots and sleeping beds. It was a great location to explore the Amish community as well as Howe Diner and touch into Michigan. It was nice to have a great place to play cards and relax after an adventure and show and Shipshewana."
The price is AED 404
AED 1,020 total
includes taxes & fees
26 Mar - 27 Mar
Live & Love Life on the Lake at Sunset Peak!
Lake Retreat With Hot Tub
Fridge, microwave, oven, stovetop

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 549
AED 697 total
includes taxes & fees
20 Apr - 21 Apr
Lake Retreat With Hot Tub
Davis Street Shipshewana
Smart TV

Davis Street Shipshewana

10.0 out of 10, Exceptional, (68)
"Short stay this time but love the place. Had everything we need. Great location, clean, well supplied. Great host, great communication. "
The price is AED 514
AED 872 total
includes taxes & fees
26 Mar - 27 Mar
Davis Street Shipshewana
Spring Sale ! Songbird Haven, 3 min from town, full house, 3 bedroom, 2 bath
Property grounds

Spring Sale ! Songbird Haven, 3 min from town, full house, 3 bedroom, 2 bath

10.0 out of 10, Exceptional, (19)
"We were delighted to find this gem of a house so close to downtown Shipshewana. Miriam was an excellent host and responded quickly to all of our questions. The property is nestled in a quiet neighborhood and was very clean and cozy. "
The price is AED 364
AED 847 total
includes taxes & fees
26 Mar - 27 Mar
Spring Sale ! Songbird Haven, 3 min from town, full house, 3 bedroom, 2 bath
Freedom Farm
Fridge, microwave, oven, stovetop

Freedom Farm

9.8 out of 10, Exceptional, (30)
"The home was clean and comfortable. When in the area again we will check on this home to see if available. The local homemade bread and apple butter were both fantasic, we went to the businesses and purchased both to bring home with us.Thank you."
Freedom Farm
Kayaks | Relax by River | 10 Min to Shipshewana |
Property grounds

Kayaks | Relax by River | 10 Min to Shipshewana |

10.0 out of 10, Exceptional, (13)
"was very clean and had everything we needed and more, great spot for bird watching too and quick trips to shipshewana."
Kayaks | Relax by River | 10 Min to Shipshewana |
The Cozy Cottage
Exterior

The Cozy Cottage

9.4 out of 10, Exceptional, (6)
"This stay was nice and quiet and not a bad drive to Notre Dame for the game. Really liked the fireplace."
The Cozy Cottage
Cozy Home Retreat
Terrace/patio

Cozy Home Retreat

2.0 star property
10.0 out of 10, Exceptional, (7)
"This property is absolutely a gorgeous house. The decorations are tasteful and beautiful. It was without a doubt the best place we have stayed in. "
The price is AED 551
AED 1,246 total
includes taxes & fees
26 Mar - 27 Mar
Cozy Home Retreat
Peaceful lakefront home perfect for families - 2 1/2 hours from Chicago
Exterior

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
Property grounds

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (143)
"Stayed 4 times. It’s always perfect. "
The price is AED 364
AED 586 total
includes taxes & fees
14 Apr - 15 Apr
Charming farmhouse in peaceful countryside
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Smart TV, books

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

10.0 out of 10, Exceptional, (15)
"The property was clean. The location was private and beautiful - a great getaway for my wife and me. We were only there 2 nights, but it was restful and enjoyable. Communication from the owners was great. We would not hesitate to book there again. "
The price is AED 477
AED 1,155 total
includes taxes & fees
7 Apr - 8 Apr
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!
Outdoor pool

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

10.0 out of 10, Exceptional, (24)
"The stay was just arpund the corber from our home but felt like a getaway!"
The price is AED 511
AED 1,362 total
includes taxes & fees
26 Mar - 27 Mar
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Channel Front Lake Wawasee
Miscellaneous

Channel Front Lake Wawasee

9.6 out of 10, Exceptional, (21)
"Loved the location and dock. Fun Lake with easy access from the rental."
Channel Front Lake Wawasee
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Outdoor spa tub

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (48)
"Loved the property. Perfect for our family of"older kids". The ping pong table and hot tub got plenty of use! "
The price is AED 465
AED 917 total
includes taxes & fees
2 Apr - 3 Apr
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Summer Sizzle! 6-Bed Channel Home!
Interior

Summer Sizzle! 6-Bed Channel Home!

9.8 out of 10, Exceptional, (25)
"Really nice place with plenty of space."
The price is AED 926
AED 2,361 total
includes taxes & fees
26 Mar - 27 Mar
Summer Sizzle! 6-Bed Channel Home!
Charming, Beautiful 5-bedroom house in wonderful Shipshewana with WiFi, Hot Tub.
Terrace/patio

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"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
Property grounds

Choo Choo Inn

10.0 out of 10, Exceptional, (16)
"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 491
AED 570 total
includes taxes & fees
6 Apr - 7 Apr
Choo Choo Inn
Beautiful 6 bedroom lake house with pontoon available for rent
Fridge, microwave, oven, stovetop

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!
Miscellaneous

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!
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
Fridge, microwave, oven, stovetop

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

2.0 star property
9.8 out of 10, Exceptional, (7)
"Mike was a great host "
The price is AED 422
AED 531 total
includes taxes & fees
26 Mar - 27 Mar
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Smart TV, books

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

10.0 out of 10, Exceptional, (15)
"The property was clean. The location was private and beautiful - a great getaway for my wife and me. We were only there 2 nights, but it was restful and enjoyable. Communication from the owners was great. We would not hesitate to book there again. "
The price is AED 477
AED 1,155 total
includes taxes & fees
7 Apr - 8 Apr
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Outdoor spa tub

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (48)
"Loved the property. Perfect for our family of"older kids". The ping pong table and hot tub got plenty of use! "
The price is AED 465
AED 917 total
includes taxes & fees
2 Apr - 3 Apr
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
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.