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Compare 174 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, (231)
"Excellent area."
The price is SAR 506
SAR 743 total
includes taxes & fees
18 Mar - 19 Mar
Recently renovated country cottage, 2.5 miles from Shipshewana

Live & Love Life on the Lake at Sunset Peak!

10.0 out of 10, Exceptional, (3)
"Very nice view over the lake all it needs is a washer and drier"
The price is SAR 405
SAR 1,033 total
includes taxes & fees
16 Mar - 17 Mar
Live & Love Life on the Lake at Sunset Peak!

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

10.0 out of 10, Exceptional, (19)
"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."
The price is SAR 371
SAR 869 total
includes taxes & fees
18 Mar - 19 Mar
Spring Sale ! Songbird Haven, 3 min from town, full house, 3 bedroom, 2 bath

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

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

Lake House | Kayaks | Patio/Deck | Private Pier

2.0 star property
10.0 out of 10, Exceptional, (7)
"Lovely home, just as described. No dishwasher, but otherwise a completely delightful place for our Thanksgiving gathering! "
The price is SAR 725
SAR 1,341 total
includes taxes & fees
5 Apr - 6 Apr
Lake House | Kayaks | Patio/Deck | Private Pier

Summer Sizzle! 6-Bed Channel Home!

10.0 out of 10, Exceptional, (24)
"Great accommodations for our needs. Very good communication with host."
The price is SAR 900
SAR 2,352 total
includes taxes & fees
17 Mar - 18 Mar
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, (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.

Cozy Lake House On The Channel With Access To 5 Lakes!

9.8 out of 10, Exceptional, (31)
"The was super clean and well equipped"
The price is SAR 638
SAR 1,042 total
includes taxes & fees
16 Mar - 17 Mar
Cozy Lake House On The Channel With Access To 5 Lakes!

Howe Retreat w/ Fire Pit + Private Boat Dock!

2.0 star property
9.8 out of 10, Exceptional, (42)
"Not enough parking. Had two trucks. Snow was not removed at the front door and side walk. "
Howe Retreat w/ Fire Pit + Private Boat Dock!

Davis Street Shipshewana

10.0 out of 10, Exceptional, (66)
"A nice house in a quiet neighborhood "
The price is SAR 413
SAR 756 total
includes taxes & fees
25 Mar - 26 Mar
Davis Street Shipshewana

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 SAR 563
SAR 1,273 total
includes taxes & fees
25 Mar - 26 Mar
Cozy Home Retreat

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 SAR 521
SAR 1,390 total
includes taxes & fees
25 Mar - 26 Mar
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Spacious Syracuse Getaway w/ Waterfront Deck!

9.8 out of 10, Exceptional, (20)
"Really beautiful lake property with easy-access dock. We brought our own boat since the pontoon season was over, but the canals to the house were easy to navigate and really a lot of fun to use. Firepit was great, and the outdoor spaces (deck, grill, etc.) were really enjoyable. The house does have a few "rustic" touches, but we were extremely comfortable, and it was the first time staying in an A-frame house. We recommend the experience!"
Spacious Syracuse Getaway w/ Waterfront Deck!

Lake Retreat With Hot Tub

10.0 out of 10, Exceptional, (15)
"Had a great Spring Break stay on this property. Nice and secluded area. Hot tub was a huge bonus. Very clean."
The price is SAR 583
SAR 737 total
includes taxes & fees
13 Apr - 14 Apr
Lake Retreat With Hot Tub

Log Cabin Haus in Amish Country Shipshewana, Indiana

10.0 out of 10, Exceptional, (14)
"Beautiful little place to stay! Very clean, very comfortable, very quiet little neighborhood. Came here for a holiday getaway with my wife, son, and his girlfriend. "
Log Cabin Haus in Amish Country Shipshewana, Indiana

Freedom Farm

9.8 out of 10, Exceptional, (29)
"The house worked very well for a few days as we had some repairs done to our RV. Very dog friendly with a fence. Nice home that has been redone / redecorated to fit the Amish area it is in with all the amenities. Michele the manager is very guest focused. Would stay again if in the area. "
Freedom Farm

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (143)
"Stayed 4 times. It’s always perfect. "
Charming farmhouse in peaceful countryside

CozyHome-HotTub-Pool-WI-FI-KingBed-ArcadeGames-PoolTable

10.0 out of 10, Exceptional, (1)
"What a perfect house and stay!!! Thank you so much for your welcoming home. We booked last minute to see the Notre Dame playoff game (Go Irish!!!) and couldn’t have been more delighted with the beautiful house and welcoming accommodations. Great hosts and house. Highly recommend. "
CozyHome-HotTub-Pool-WI-FI-KingBed-ArcadeGames-PoolTable

Lakefront Family Home in Three Rivers!

10.0 out of 10, Exceptional, (1)
"Stayed here for a weekend for an extended family reunion and this VRBO was well stocked - it had everything you could need! Picked this location for its proximity to Swiss Valley Ski Resort. Warm weather deterred our plans but honestly this might have been in our favor - no one had any complaints and we all enjoyed the comforts of this cozy home and the extra quality time! Thanks for a wonderful stay! Already talks of returning next year. "
Lakefront Family Home in Three Rivers!
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

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 469
SAR 1,148 total
includes taxes & fees
25 Mar - 26 Mar
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Freedom Farm

9.8 out of 10, Exceptional, (29)
"The house worked very well for a few days as we had some repairs done to our RV. Very dog friendly with a fence. Nice home that has been redone / redecorated to fit the Amish area it is in with all the amenities. Michele the manager is very guest focused. Would stay again if in the area. "
Freedom Farm

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 SAR 413
SAR 522 total
includes taxes & fees
17 Mar - 18 Mar
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
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.