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Middlebury Vacation 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., vacation rental in Middlebury

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

3 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Carefree Cottage on the Lake, vacation 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!!, vacation rental in Middlebury

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

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

Executive Home directly across from Syracuse Lake! Sleeps 10!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Newly renovated country cottage, 2.5 miles from Shipshewana, relaxing fountain, vacation 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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Family Friendly Lakefront Cottage with Breathtaking Sunsets, vacation rental in Middlebury

Family Friendly Lakefront Cottage with Breathtaking Sunsets

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Chic Guest House Retreat, vacation rental in Middlebury

Chic Guest House Retreat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Visit Shipshewana for the holidays! All new in 2020;  Peaceful on Dallas Lake, vacation 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!, vacation rental in Middlebury

Best Sunset on the Lake!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Adorable Lakeside Dream, vacation rental in Middlebury

Adorable Lakeside Dream

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

Beautiful lake getaway in a great central location

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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4BR / 2.5 BA Family friendly get away for lake fun and college football!, vacation rental in Middlebury

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

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cute weekly seasonal rental in Oakwood Park, Lake Wawasee/Syracuse Indiana, vacation rental in Middlebury

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake Wawasee Cottage overlooking Johnson Bay, vacation rental in Middlebury

Lake Wawasee Cottage overlooking Johnson Bay

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Fish Lake - All Sports Lake Front Cottage, Shopping & Notre Dame, vacation rental in Middlebury

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

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Little Cottage On The Lake, vacation rental in Middlebury

Cozy Little Cottage On The Lake

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Great Location With Lake Access On Beautiful Lake Wawasee!, vacation rental in Middlebury

Great Location With Lake Access On Beautiful Lake Wawasee!

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Stylish, newly remodeled cottage on Dallas Lake, vacation rental in Middlebury

Stylish, newly remodeled cottage on Dallas Lake

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Beautiful Home on the River, vacation rental in Middlebury

Beautiful Home on the River

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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GORGEOUS!!!  Open concept renovation. Wawasee, Oakwood Park water front!, vacation 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., vacation rental in Middlebury

Very Clean Lakefront Home with Sandy Beach and Clear water.

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Spacious Lake Home Close To Notre Dame, vacation rental in Middlebury

Spacious Lake Home Close To Notre Dame

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

Gorgeous Klinger Lake house White Pigeon, MI

4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Paradise on the lake!, vacation 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, vacation 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, vacation 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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NEW! Cozy Dairy Farm Studio, 14 Mi to Shipshewana, vacation rental in Middlebury

NEW! Cozy Dairy Farm Studio, 14 Mi to Shipshewana

0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Weekly Vacation Cottage Rental on the lake, vacation 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, vacation 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, vacation 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, vacation 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, vacation 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!, vacation 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, vacation 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, vacation 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!, vacation 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!, vacation 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!, vacation 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!, vacation 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., vacation 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! Authentic Dairy Farm Retreat in Amish Country, vacation rental in Middlebury

NEW! Authentic Dairy Farm Retreat in Amish Country

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Primitive Amish Home to Rest, Relax & Rejuvenate. Experience a simple lifestyl, vacation rental in Middlebury

Primitive Amish Home to Rest, Relax & Rejuvenate. Experience a simple lifestyl

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lighthouse Point At Pleasant Lake: Lakeside & Sunsets, vacation rental in Middlebury

Lighthouse Point At Pleasant Lake: Lakeside & Sunsets

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Stunning Shipshewana Home on Private Hilltop!, vacation rental in Middlebury

NEW! Stunning Shipshewana Home on Private Hilltop!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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ND GAME DAY EAGLE LAKE FRONT with best views of the lake and sandy beach, vacation 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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