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Vacation Homes in Middlebury

Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks

10.0 out of 10, Exceptional, (7)
Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks

South Shore Sunrise: 100% Renovated Lake Home, Pontoon INCLUDED, near Notre Dame

10.0 out of 10, Exceptional, (30)
"Had a great time celebrating birthdays with good friends at this beautiful home."
South Shore Sunrise: 100% Renovated Lake Home, Pontoon INCLUDED, near Notre Dame

Millie's Cottage

10.0 out of 10, Exceptional, (263)
"Very clean, cozy, and a great location!! Great communication with the host!We enjoyed our stay very much!! Highly recommend!!"
Millie's Cottage

Cozy Home Retreat

2.0 star property
9.8 out of 10, Exceptional, (18)
"The house was furnished very nicely. It felt cozy and clean. Location was very close to the Shipshewana shops and entertainment. "
Cozy Home Retreat

Cottages on Sand Lake - The Lazy Lakehouse

10.0 out of 10, Exceptional, (11)
"A cute cabin with a very nice lake! Walking distance to the wedding we were attending at Twin Gables Event Center. This place fit our needs perfectly."
Cottages on Sand Lake - The Lazy Lakehouse

Kayaks | Relax by River | 10 Min to Shipshewana |

10.0 out of 10, Exceptional, (18)
"Cozey little get away. Clean and updated with a beautiful view. We enjoyed our stay here. "
The price is ¥13,711
¥30,014 total
includes taxes & fees
Aug 21 - Aug 22
Kayaks | Relax by River | 10 Min to Shipshewana |

Herons Perch: Peaceful Lakefront Cottage in Shipshewana close to all the fun!

10.0 out of 10, Exceptional, (1)
"Heron's Perch was a great spot for our family reunion. Such a cute, little cottage with something for everyone-games, kayaks, fishing, beautiful sunsets, etc., not to mention close by options in Shipshewana and Middlebury. The owners, who have a seasonal home next door, were very friendly and helpful. Highly recommend! "
Herons Perch: Peaceful Lakefront Cottage in Shipshewana close to all the fun!

Charming 3-bedroom house located on Main Street in Downtown Middlebury

10.0 out of 10, Exceptional, (2)
"Beautiful cute cottage.. very clean,everything and anything we could possibly want or need! Plenty of room for our family of 9, and just absolutely perfect and lovely. Great location. Grocery store and cute little ice cream shop within walking distance. Thanks so much!!"
The price is ¥28,349
¥43,720 total
includes taxes & fees
Aug 19 - Aug 20
Charming 3-bedroom house located on Main Street in Downtown Middlebury

Beautiful Waterfront Home on Baugo Bay

9.6 out of 10, Exceptional, (29)
"Gregg's home was very neat, clean and had everything you could need. The view was beautiful. Thank you for a great stay."
The price is ¥73,595
¥96,652 total
includes taxes & fees
Aug 25 - Aug 26
Beautiful Waterfront Home on Baugo Bay

Perfect Vacation Home! 2 Master Suites! Game Rm Arcade Fish Kayak 15 Mins to ND

10.0 out of 10, Exceptional, (97)
"The house is large with a lot of fun amenities. Would definitely stay here again."
Perfect Vacation Home! 2 Master Suites! Game Rm Arcade Fish Kayak 15 Mins to ND

Beautiful cozy cottage 1 block from the lake and Oakwood hotel.

9.6 out of 10, Exceptional, (29)
"We loved this cozy cottage! We were in town for a wedding and it was perfect! "
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.

Emma's Place

10.0 out of 10, Exceptional, (53)
"This is a beautiful house. Very clean nice fenced in back yard. Real quiet location. Host is very friendly. We will stay here again if it is available our next trip back."
The price is ¥22,079
¥45,830 total
includes taxes & fees
Aug 20 - Aug 21
Emma's Place

Beautiful Lake house with private sandy beach, kayaks, 5 beds, 5 bath and spa!

2.0 star property
10.0 out of 10, Exceptional, (4)
"House was extremely nice and clean. Beach and lake area very nice too."
Beautiful Lake house with private sandy beach, kayaks, 5 beds, 5 bath and spa!

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

10.0 out of 10, Exceptional, (24)
"House and property had more than enough activities to keep up completely entertained for our entire stay. Loved the game room, pickleball court, hot tub and kayaks!!"
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (155)
"It was a nice spot, near to the events we took in, over the weekend."
Charming farmhouse in peaceful countryside

Live & Love Life on the Lake at Sunset Peak!

10.0 out of 10, Exceptional, (15)
"We loved our long weekend getaway! "
The price is ¥19,208
¥44,924 total
includes taxes & fees
Aug 19 - Aug 20
Live & Love Life on the Lake at Sunset Peak!

See the Diamonds Sparkle on the Lake. Enjoy your family memories for a lifetime.

9.8 out of 10, Exceptional, (17)
"Fantastic property on a great part of the lake. Could not have enjoyed the week more. Ownerships was very attentive. Will stay again."
See the Diamonds Sparkle on the Lake. Enjoy your family memories for a lifetime.

Enjoy amazing views, sunsets & conversations by the fire on our huge flat lawn

9.6 out of 10, Exceptional, (66)
"We had a great time staying in Jeff’s home for the week, we were very comfortable and had plenty of room for all of us. The kitchen was well stocked with all the appliances and things you may need. We enjoyed spending time there making dinner to eat out on the patio. We sat around the firepit in the eve and the kids had a fun time playing in the yard. They loved the hammock and swing. We especially loved the boat! Spent quite a lot of time at the sand bar! Will definitely stay again!"
Enjoy amazing views, sunsets & conversations by the fire on our huge flat lawn

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

10.0 out of 10, Exceptional, (7)
"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

Water’s Edge Retreat, Charming 2-bedroom Lake House, marvelous Shipshewana

10.0 out of 10, Exceptional, (3)
"The house was perfect. Very clean, organized, and stressfree! I would gladly stay here again. The lake was so peaceful and relaxing."
Water’s Edge Retreat, Charming 2-bedroom Lake House, marvelous Shipshewana
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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Top Middlebury Hotel Reviews