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Compare 164 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, (223)
"Enjoyed the adorable little house decorated for fall. We always smiled returning to the property from a day in town. Well stocked kitchen and bathroom. Very clean. Would definitely stay again."
The price is SAR 507
SAR 736 total
includes taxes & fees
21 Nov - 22 Nov
Recently renovated country cottage, 2.5 miles from Shipshewana
Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,
Property grounds
Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,
10.0 out of 10, Exceptional, (15)
"Great location, so peaceful, very comfortable and welcoming."
The price is SAR 507
SAR 1,060 total
includes taxes & fees
20 Nov - 21 Nov
Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,
Charming 1912 Bungalow in Middlebury Indiana
Nothing like a fire in the fireplace on a chilly morning/evening.
Charming 1912 Bungalow in Middlebury Indiana
10.0 out of 10, Exceptional, (35)
"This was the most comfortable home ever! My family and I are already planning on staying there in the spring. "
Charming 1912 Bungalow in Middlebury Indiana
Davis Street Shipshewana
Exterior
Davis Street Shipshewana
9.8 out of 10, Exceptional, (60)
"Nice neighborhood. Convenient to tourist attractions."
The price is SAR 413
SAR 769 total
includes taxes & fees
24 Nov - 25 Nov
Davis Street Shipshewana
Secluded Riverside Log Home in Southern Michigan
Exterior
Secluded Riverside Log Home in Southern Michigan
10.0 out of 10, Exceptional, (74)
"It was supposed to be a gathering of siblings and spouses each traveling from a couple hours away. A getaway for seven turned into a fun weekend for four. One missed because of illness. Two missed because of a family death the day we were supposed to stay. Owners were very sympathetic and understanding of the situation. The four who stayed had a good time and we hope to book again for a more complete siblings weekend."
Secluded Riverside Log Home in Southern Michigan
Shipshewana Guest House with Fire Pit!
Shipshewana Vacation Rental | 1BR | 1BA | 1,536 Sq Ft | Step-Free Access
Shipshewana Guest House with Fire Pit!
10.0 out of 10, Exceptional, (30)
"What great home base for a girls trip. Guest house is beautiful, serene and a little slice of heof the experience in Shipshewana!"
Shipshewana Guest House with Fire Pit!
⚓️Direct lake view with available Tritoon boat rental
Direct view of Lake, Wawasee with new addition
⚓️Direct lake view with available Tritoon boat rental
9.8 out of 10, Exceptional, (7)
"The house was better than we expected. It had everything we needed. Communication with owner was good! Neighbors were lovely. Would stay again. "
⚓️Direct lake view with available Tritoon boat rental
Tranquil lakeside retreat
Exterior
Tranquil lakeside retreat
10.0 out of 10, Exceptional, (9)
"Everything was wonderful and we really enjoyed the kayaks/paddleboat. Very functional for a 3 week stay. Only suggestion is an exhaust fan in bathroom would have been helpful when we had to all shower. (Little window opens and it helped) "
Tranquil lakeside retreat
Cozy Sylvan Lake Cabin with Loft & Stunning Lake Views!
Exterior
Cozy Sylvan Lake Cabin with Loft & Stunning Lake Views!
10.0 out of 10, Exceptional, (23)
"Quiet place to relax and enjoy a great view!"
Cozy Sylvan Lake Cabin with Loft & Stunning Lake Views!
Game Room | Pool Table | Foosball|Family Focused|
Whether you're with family or friends, our basement Game Room is the perfect place to let loose and get competitive!! You'll find a high-quality pool table, foosball table, and carpet ball table, plus a great high table for board games and card games!
Game Room | Pool Table | Foosball|Family Focused|
10.0 out of 10, Exceptional, (25)
"I like to keep secrets when it comes to finding gems like this, but to benefit the host will share… We had an amazing time. The home was cozy and comfortable, offering all the expected amenities. We enjoyed watching the buggies go by from the living room and from the covered front porch. The game room was an added bonus. This home was super clean and well stocked. There were plenty of activities in the area to keep us entertained through out the day. I believe this was, by far, the best VRBO...
The price is SAR 250
SAR 652 total
includes taxes & fees
12 Dec - 13 Dec
Game Room | Pool Table | Foosball|Family Focused|
Country Cottage
Room
Country Cottage
10.0 out of 10, Exceptional, (18)
"Exactly like the other reviews. The only thing I would change is larger shower heads . Takes forever to rinse your hair. "
Country Cottage
Destination lake, Million dollar house, million-dollar views
Street side
Destination lake, Million dollar house, million-dollar views
10.0 out of 10, Exceptional, (7)
"We had a couple small families from all over the US and we all had so much fun! Plenty of room for he kiddos and the place had a lot to offer! Will definitely come back again! "
Destination lake, Million dollar house, million-dollar views
Log Cabin Haus in Amish Country Shipshewana, Indiana
Welcome to Log Cabin Haus!
Log Cabin Haus in Amish Country Shipshewana, Indiana
10.0 out of 10, Exceptional, (12)
"Our group enjoyed our weekend. The only complaint was no television (my fault). I forgot about the football games this weekend. The ramp was very handy especially when lugging in the necessities. The sounds of the horses was very relaxing. "
Log Cabin Haus in Amish Country Shipshewana, Indiana
Barn! Golf Sim/Theater, Bunk Slide, Mini Golf, Hot Tub, Saloon Bar, Firepit!
Exterior
Barn! Golf Sim/Theater, Bunk Slide, Mini Golf, Hot Tub, Saloon Bar, Firepit!
Barn! Golf Sim/Theater, Bunk Slide, Mini Golf, Hot Tub, Saloon Bar, Firepit!
Charming farmhouse in peaceful countryside
Living area
Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (132)
"3rd time staying at the same house. It’s been great every time!"
Charming farmhouse in peaceful countryside
Emma's Place
Private kitchen
Emma's Place
10.0 out of 10, Exceptional, (37)
"We stayed one night and were very comfortable. The house was very clean and easy to find. "
The price is SAR 563
SAR 1,177 total
includes taxes & fees
25 Nov - 26 Nov
Emma's Place
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
Property grounds
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, (8)
"So many stairs. Haha, it was good though. Kayaks and paddle boat were fun exercise as well. Relaxing on the top deck with the amazing view was exactly what I needed. "
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
Terrace/patio
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
10.0 out of 10, Exceptional, (14)
"Very convenient location, close to the toll road. Very clean house, beautiful country setting. We would recommend this to anyone."
The price is SAR 450
SAR 1,193 total
includes taxes & fees
2 Dec - 3 Dec
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Lake cottage with a great view 20 minutes from Shipshewana.
View of house from lakefront. New deck and steps.
Lake cottage with a great view 20 minutes from Shipshewana.
10.0 out of 10, Exceptional, (88)
"The communication was great. The house was very clean. Deck has great view of the lake. The flower gardens around the house added special touch. Hope to stay there again in warm weather."
Lake cottage with a great view 20 minutes from Shipshewana.
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Pool
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
10.0 out of 10, Exceptional, (21)
"We loved everything the pool,hot tub,game room, and the cozy house we definitely loved to come back "
The price is SAR 563
SAR 1,442 total
includes taxes & fees
12 Dec - 13 Dec
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
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

The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Terrace/patio
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
10.0 out of 10, Exceptional, (14)
"Very convenient location, close to the toll road. Very clean house, beautiful country setting. We would recommend this to anyone."
The price is SAR 450
SAR 1,193 total
includes taxes & fees
2 Dec - 3 Dec
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Welcome to your Home Away From Home! Beautiful backyard and hot tub! Can't you see yourself relaxing the evening away?
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
10.0 out of 10, Exceptional, (45)
"The house was beautiful! Very comfortable and welcoming. Will definitely stay here again if in the area!"
The price is SAR 661
SAR 1,141 total
includes taxes & fees
30 Nov - 1 Dec
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
Property grounds
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, (8)
"So many stairs. Haha, it was good though. Kayaks and paddle boat were fun exercise as well. Relaxing on the top deck with the amazing view was exactly what I needed. "
Amazing view of Stone Lake from top deck. Thirty five miles from 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.