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Compare 161 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, (210)
"Wanting to get away to celebrate our 33rd anniversary. Had a wonderful time in the area. The house was great, it was quiet and had a nice sunrise in the morning. Good location close to shopping and eating."
The price is AED 533
AED 683 total
includes taxes & fees
29 Sep - 30 Sep
Recently renovated country cottage, 2.5 miles from Shipshewana
Cozy Home Retreat
2.0 star property
10.0 out of 10, Exceptional, (4)
"This cute ranch is very clean and well stocked for guests. We only had three people in our group, but the house can definitely host more people comfortably. It is very close to downtown Shipshewana and other surrounding shops and attractions. My only suggestion would possibly be investing in new mattresses. Although we slept comfortably, the quality could be improved. The owner was responsive to my messages in a timely manner. Instructions for the home were clear and easy to follow. We would...
The price is AED 661
AED 1,407 total
includes taxes & fees
30 Sep - 1 Oct
Cozy Home Retreat
Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (126)
"We absolutely loved staying here with the kids. The house and the farm are beautiful with so much attention to every single detail. Michelle and her family are so welcoming they made us feel at home away from home. And then there’s Dixie, such a good dog! I really hope we have the chance to come back again soon. "
Charming farmhouse in peaceful countryside
Newly Remodeled Cabin Steps from Sylvan Lake
10.0 out of 10, Exceptional, (29)
"This is the second time we have rented this sweet cottage for a long summer weekend. Property is very clean and is convenient to beach, grocery and is just steps from the lake. Beautiful views, quiet neighborhood. "
Newly Remodeled Cabin Steps from Sylvan Lake
⚓️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
Game Room | Pool Table | Foosball|Family Focused|
10.0 out of 10, Exceptional, (20)
"The property was clean and comfortable with a great game room in the basement. An added bonus was the availability to store and charge our e-bikes in the garage. Also we were able to take a safer route through the neighborhood across the street on our e-bikes in order to reach the Pumpkinvine Trail. (which is around 1/2 mile from the home. We also could watch the Amish buggies go down the street right out the front window. The property manager was very accommodating and quick to respond to any...
The price is AED 300
AED 697 total
includes taxes & fees
16 Oct - 17 Oct
Game Room | Pool Table | Foosball|Family Focused|
Spacious Syracuse Getaway w/ Waterfront Deck!
9.8 out of 10, Exceptional, (19)
"We stayed for a long weekend with our adult children and grandchildren. The house is on a quiet channel of the lake. Great yard and firepit. Renting the pontoon boat was a nice addition. The house had plenty space for everyone. I would mention that the loft with the twin beds is at the top of a narrow spiral staircase - so fine for kids or teens but wouldn't work for all. The yard is large enough that there is room for the kids to play without being too close to the water. The house is...
Spacious Syracuse Getaway w/ Waterfront Deck!
Shipshewana Guest House with Fire Pit!
10.0 out of 10, Exceptional, (26)
"Highly recommended."
Shipshewana Guest House with Fire Pit!
Freedom Farm
10.0 out of 10, Exceptional, (26)
"The home is set in a beautiful farming community. The home is on a farm, which was a reminder of my family home. We enjoyed seeing the horses, ducks and chickens "
Freedom Farm
`Burning Pine Inn' Farm House in Amish country.
10.0 out of 10, Exceptional, (11)
"Great"
`Burning Pine Inn' Farm House in Amish country.
Cassopolis Vacation Home - Walk to Diamond Lake!
8.8 out of 10, Excellent, (3)
"The house was amazing we would recommend this property - very spacious, and stocked well. The pool was a great addition and enjoyed by all.There were many flotation toys & beach towels available however, it could have been cleaned a little better prior to our arrival. The outside area was very nice with many tables, chairs & lounge chairs. We enjoyed playing basketball and the fire pit area was nice. Diamond Lake is within walking distance but there is no public access near by. The...
Cassopolis Vacation Home - Walk to Diamond Lake!
Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,
10.0 out of 10, Exceptional, (11)
"Miriam's home is wonderful and has everything to make your stay feel like home. This is the second time we have stayed at her place and will do so in the future. The neighborhood is quiet and the perfect place to unwind. Close to all of the attractions. She is attentive to her guests needs and responds immediately. We look forward to future stays. "
Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,
| Hot Tub | Amish Farm Country | Pergola | Deck |
10.0 out of 10, Exceptional, (70)
"The property was very clean. Location was perfect. We was in town to go to the Flea Market in Shipshewana. It was only maybe 7 miles away. But got to view the beautiful countryside. Definitely planning to go back and we will check into renting this VRBO again. "
The price is AED 309
AED 749 total
includes taxes & fees
3 Oct - 4 Oct
| Hot Tub | Amish Farm Country | Pergola | Deck |
Kayaks | Relax by River | 10 Min to Shipshewana |
10.0 out of 10, Exceptional, (6)
"The property was beautifully appointed! There were lots of fluffy towels. Everything was immaculately clean. The host was wonderful and answered any questions in a very timely matter"
Kayaks | Relax by River | 10 Min to Shipshewana |
Rocky River Resort
9.8 out of 10, Exceptional, (9)
"The property was wonderful, the pool was a fan fav for sure. I loved that there was room for everyone to spread out and have time to themself and still have family time together. Mike is a wonderful host!!! "
Rocky River Resort
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
9.8 out of 10, Exceptional, (18)
"we enjoyed our stay. The pool was perfect cool often after a long hot day out. Hot tub wasn’t added bonus as we were playing tennis and it helped us relax our muscles at night. The living room was nice and large host. Everyone at night to play games and hang out. "
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
Emma's Place
10.0 out of 10, Exceptional, (34)
"Very accommodating "
The price is AED 551
AED 1,152 total
includes taxes & fees
23 Sep - 24 Sep
Emma's Place
Beautiful Waterfront Home on Baugo Bay
9.8 out of 10, Exceptional, (24)
"The views from the decks are beautiful. The house does sleep 10 but there are not 4 bedrooms; really only 2. We ended up renting a boat on a different lake because the St Joseph River is not good for a novice boat driver, plus the boat at the house was not operating. Hot tub was great but there is no fire pit. All in all we had a nice peaceful time with family and enjoyed the sunset."
The price is AED 1,837
AED 2,412 total
includes taxes & fees
30 Sep - 1 Oct
Beautiful Waterfront Home on Baugo Bay
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
10.0 out of 10, Exceptional, (13)
"Three guys in Indiana to golf with a local friend. Location great."
The price is AED 514
AED 1,258 total
includes taxes & fees
23 Sep - 24 Sep
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Secluded Riverside Log Home in Southern Michigan
10.0 out of 10, Exceptional, (73)
"Great location, great host, definitely would come back. "
Secluded Riverside Log Home in Southern Michigan
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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

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
10.0 out of 10, Exceptional, (42)
"I was slightly apprehensive about renting a vacation spot that I was totally unfamiliar with. BUT, once we arrived I was TOTALLY delighted! The house was clean and well stocked with everything we needed. The back yard truly was a private oasis. And, we absolutely loved the ping pong AND the cornhole boards! I would definitely recommend! Todd was the greatest!"
The price is AED 547
AED 1,021 total
includes taxes & fees
4 Oct - 5 Oct
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
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
10.0 out of 10, Exceptional, (13)
"Three guys in Indiana to golf with a local friend. Location great."
The price is AED 514
AED 1,258 total
includes taxes & fees
23 Sep - 24 Sep
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.