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Holiday Homes in Middlebury

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Featured Holiday Homes in Middlebury

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

10.0 out of 10, Exceptional, (31)
"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

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 AU$493
includes taxes & fees
27 Aug - 28 Aug
Emma's Place

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

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 AU$503
includes taxes & fees
24 Aug - 25 Aug
Charming 3-bedroom house located on Main Street in Downtown Middlebury

Lake cottage with a great view. Sylvan Cellars is 10 minutes away.

10.0 out of 10, Exceptional, (92)
"Well kept place on the lake!"
Lake cottage with a great view. Sylvan Cellars is 10 minutes away.

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

Newly Remodeled Cabin Steps from Sylvan Lake

10.0 out of 10, Exceptional, (43)
"Nice little place for my wife and I prior to a state conference. Good access to lake and kayaks were provided. Good proximity to Amish country. "
Newly Remodeled Cabin Steps from Sylvan Lake

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

Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

10.0 out of 10, Exceptional, (2)
"This residence was exceptionally clean and featured a very well-equipped kitchen with top-of-the-line cooking equipment. It was the perfect place to entertain teenagers, offering plenty of activities such as a pool, basketball hoops, an infinity game table, ping pong and more. There was lots of space for everyone to spread out, making it easy to enjoy different activities simultaneously without feeling crowded. A fantastic setup for a fun and relaxing stay!"
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

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 AU$535
includes taxes & fees
29 Aug - 30 Aug
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!

Lake Retreat With Hot Tub

10.0 out of 10, Exceptional, (21)
"This was perfect for our short getaway!"
The price is AU$314
includes taxes & fees
28 Aug - 29 Aug
Lake Retreat With Hot Tub

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

Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!

9.2 out of 10, Wonderful, (20)
"My family enjoyed this property. Very spacious and plenty to do. Could use many updates. Has great potential to be a beautiful property. Owner responds quickly if needed when staying at property. Overall would stay again. "
Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!

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!

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

10.0 out of 10, Exceptional, (26)
"The stay was just arpund the corber from our home but felt like a getaway!"
The price is AU$748
includes taxes & fees
4 Sept - 5 Sept
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

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

10.0 out of 10, Exceptional, (22)
"We stayed just one night and it was lovely. The home was spotless and very cute, and it was decorated so cute. "
The price is AU$491
includes taxes & fees
2 Sept - 3 Sept
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

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

9.4 out of 10, Exceptional, (30)
"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.

Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

10.0 out of 10, Exceptional, (25)
"House was very clean, well stocked and a beautiful location. Easy access to town as well. Loved our stay!!!"
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (58)
"Very clean, nicely appointed. Ping pong table and hot tub were a real bonus! "
The price is AU$416
includes taxes & fees
14 Sept - 15 Sept
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.
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Top Middlebury Hotel Reviews