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Middlebury Holiday Rentals

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47 rentals in Middlebury.
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The Wellington Lake Cottage on Stone Lake Middlebury, IN 3 bed 4 bath for 8., holiday rental in Middlebury

The Wellington Lake Cottage on Stone Lake Middlebury, IN 3 bed 4 bath for 8.

3 bedrooms
6 bathrooms
Sleeps 8
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White Loft On Scott, holiday rental in Middlebury

White Loft On Scott

1 bedroom
1 bathroom
Sleeps 2
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Carefree Cottage on the Lake, holiday rental in Middlebury

Carefree Cottage on the Lake

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful and Historic Log Cabin for family or couple getaway - huge hot tub!!, holiday rental in Middlebury

Beautiful and Historic Log Cabin for family or couple getaway - huge hot tub!!

2 bedrooms
2 bathrooms
Sleeps 6
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A quiet place for a get-away. 15 minutes from Shipshewana., holiday rental in Middlebury

A quiet place for a get-away. 15 minutes from Shipshewana.

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Executive Home directly across from Syracuse Lake! Sleeps 10!, holiday rental in Middlebury

Executive Home directly across from Syracuse Lake! Sleeps 10!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Chic Guest House Retreat, holiday rental in Middlebury

Chic Guest House Retreat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Family Friendly Lakefront Cottage with Breathtaking Sunsets, holiday rental in Middlebury

Family Friendly Lakefront Cottage with Breathtaking Sunsets

3 bedrooms
2 bathrooms
Sleeps 10
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Modern Farmhouse Lakeside, holiday rental in Middlebury

Modern Farmhouse Lakeside

3 bedrooms
2 bathrooms
Sleeps 8
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Visit Shipshewana for the holidays! All new in 2020;  Peaceful on Dallas Lake, holiday rental in Middlebury

Visit Shipshewana for the holidays! All new in 2020; Peaceful on Dallas Lake

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Best Sunset on the Lake!, holiday rental in Middlebury

Best Sunset on the Lake!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Newly renovated country cottage, 2.5 miles from Shipshewana, relaxing fountain, holiday rental in Middlebury

Newly renovated country cottage, 2.5 miles from Shipshewana, relaxing fountain

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Adorable Lakeside Dream, holiday rental in Middlebury

Adorable Lakeside Dream

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Notre Dame Lake House Rental, holiday rental in Middlebury

Notre Dame Lake House Rental

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful lake getaway in a great central location, holiday rental in Middlebury

Beautiful lake getaway in a great central location

3 bedrooms
2 bathrooms
Sleeps 7
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Cute weekly seasonal rental in Oakwood Park, Lake Wawasee/Syracuse Indiana, holiday rental in Middlebury

Cute weekly seasonal rental in Oakwood Park, Lake Wawasee/Syracuse Indiana

2 bedrooms
1 bathroom
Sleeps 6
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Fish Lake - All Sports Lake Front Cottage, Shopping & Notre Dame, holiday rental in Middlebury

Fish Lake - All Sports Lake Front Cottage, Shopping & Notre Dame

1 bedroom
1 bathroom
Sleeps 6
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4BR / 2.5 BA Family friendly get away for lake fun and college football!, holiday rental in Middlebury

4BR / 2.5 BA Family friendly get away for lake fun and college football!

5 bedrooms
3 bathrooms
Sleeps 10
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Lake Wawasee Cottage overlooking Johnson Bay, holiday rental in Middlebury

Lake Wawasee Cottage overlooking Johnson Bay

3 bedrooms
2 bathrooms
Sleeps 8
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Great Location With Lake Access On Beautiful Lake Wawasee!, holiday rental in Middlebury

Great Location With Lake Access On Beautiful Lake Wawasee!

4 bedrooms
3 bathrooms
Sleeps 16
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Beautiful Home on the River, holiday rental in Middlebury

Beautiful Home on the River

4 bedrooms
2 bathrooms
Sleeps 10
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Cozy Little Cottage On The Lake, holiday rental in Middlebury

Cozy Little Cottage On The Lake

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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GORGEOUS!!!  Open concept renovation. Wawasee, Oakwood Park water front!, holiday rental in Middlebury

GORGEOUS!!! Open concept renovation. Wawasee, Oakwood Park water front!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Very Clean Lakefront Home with Sandy Beach and Clear water., holiday rental in Middlebury

Very Clean Lakefront Home with Sandy Beach and Clear water.

2 bedrooms
1 bathroom
Sleeps 8
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Stylish, newly remodeled cottage on Dallas Lake, holiday rental in Middlebury

Stylish, newly remodeled cottage on Dallas Lake

3 bedrooms
1 bathroom
Sleeps 8
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Spacious Lake Home Close To Notre Dame, holiday rental in Middlebury

Spacious Lake Home Close To Notre Dame

5 bedrooms
4 bathrooms
Sleeps 14
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Newly constructed home in Granger available year round, 15 minutes from N, holiday rental in Middlebury

Newly constructed home in Granger available year round, 15 minutes from N

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Klinger Lake house  White Pigeon, MI, holiday rental in Middlebury

Gorgeous Klinger Lake house White Pigeon, MI

4 bedrooms
3 bathrooms
Sleeps 13
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Paradise on the lake!, holiday rental in Middlebury

Paradise on the lake!

6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Lake Wawasee Contemporary Channel Front with Pier, holiday rental in Middlebury

Lake Wawasee Contemporary Channel Front with Pier

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Lakefront Cabin w/ Dock, 6 Mi to Swiss Valley, holiday rental in Middlebury

NEW! Lakefront Cabin w/ Dock, 6 Mi to Swiss Valley

7 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Fabulous!  2 bed/ 2 bath Guest House with Access to Your Own Private Lakeside Pa, holiday rental in Middlebury

Fabulous! 2 bed/ 2 bath Guest House with Access to Your Own Private Lakeside Pa

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Weekly Vacation Cottage Rental on the lake, holiday rental in Middlebury

Weekly Vacation Cottage Rental on the lake

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Vacation Cottage Rental On The Lake, holiday rental in Middlebury

Vacation Cottage Rental On The Lake

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Daily Vacation Cottage Rental On The Lake, holiday rental in Middlebury

Daily Vacation Cottage Rental On The Lake

1 bedroom
0 bathrooms
Sleeps 2
Match: Sleeps
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Waterfront Syracuse Home w/Deck, Fire Pit & Kayaks, holiday rental in Middlebury

Waterfront Syracuse Home w/Deck, Fire Pit & Kayaks

2 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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Lake Wawasee Channel Front with Partial Lake View, holiday rental in Middlebury

Lake Wawasee Channel Front with Partial Lake View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront Vandalia House w/ Dock on Donnell Lake!, holiday rental in Middlebury

Waterfront Vandalia House w/ Dock on Donnell Lake!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Schönbrook Farm & Inn, holiday rental in Middlebury

Schönbrook Farm & Inn

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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New Kid in Town, 2 Bedroom Channel Front Condo, holiday rental in Middlebury

New Kid in Town, 2 Bedroom Channel Front Condo

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Amish Country Cabin on Shipshewana Lake!, holiday rental in Middlebury

Cozy Amish Country Cabin on Shipshewana Lake!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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'Honey House Cabin' - A Quiet Countryside Retreat!, holiday rental in Middlebury

'Honey House Cabin' - A Quiet Countryside Retreat!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy ‘Haven of Rest’ Home w/ Amish Country Views!, holiday rental in Middlebury

Cozy ‘Haven of Rest’ Home w/ Amish Country Views!

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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'Rise and Shine Farm' in Goshen w/ BBQ & Fire Pit!, holiday rental in Middlebury

'Rise and Shine Farm' in Goshen w/ BBQ & Fire Pit!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Large Home 4 Bed, 2.5 Bath, 2400sf, Home games, parent visits. Rent all/partial., holiday rental in Middlebury

Large Home 4 Bed, 2.5 Bath, 2400sf, Home games, parent visits. Rent all/partial.

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Cozy Dairy Farm Studio, 14 Mi to Shipshewana, holiday rental in Middlebury

NEW! Cozy Dairy Farm Studio, 14 Mi to Shipshewana

0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Authentic Dairy Farm Retreat in Amish Country, holiday rental in Middlebury

NEW! Authentic Dairy Farm Retreat in Amish Country

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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ND GAME DAY EAGLE LAKE FRONT with best views of the lake and sandy beach, holiday rental in Middlebury

ND GAME DAY EAGLE LAKE FRONT with best views of the lake and sandy beach

2 bedrooms
1 bathroom
Sleeps 1
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