Book Holiday Homes in Middlebury

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Featured Holiday Homes in Middlebury

Recently renovated country cottage, 2.5 miles from Shipshewana

Recently renovated country cottage, 2.5 miles from Shipshewana

Shipshewana
Stay at this vacation home in Shipshewana. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Dutch Creek Farm Animal Park and North ...
Recently renovated country cottage, 2.5 miles from Shipshewana
Live & Love Life on the Lake at Sunset Peak!

Live & Love Life on the Lake at Sunset Peak!

Howe
The price is NZ$501 per night from 3 Apr to 4 Apr
NZ$501
includes taxes & fees
3 Apr - 4 Apr
Stay at this vacation home in Howe. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Green Valley Golf & Health Club and Oaklawn ...
Live & Love Life on the Lake at Sunset Peak!
Lake Retreat With Hot Tub

Lake Retreat With Hot Tub

Howe
The price is NZ$335 per night from 2 Apr to 3 Apr
NZ$335
includes taxes & fees
2 Apr - 3 Apr
Book a stay at this family-friendly vacation home in Howe. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Cedar Lake Golf Club and ...
Lake Retreat With Hot Tub
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Davis Street Shipshewana

Davis Street Shipshewana

Shipshewana
Stay at this vacation home in Shipshewana. Enjoy free WiFi, a garden, and patios. Our guests praise the helpful staff in our reviews. Popular attractions Shipshewana ...
Davis Street Shipshewana
Spring Sale ! Songbird Haven, 3 min from town, full house, 3 bedroom, 2 bath

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

Shipshewana
Stay at this vacation home in Shipshewana. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions North Park and Blue Gate Theater are located ...
Spring Sale ! Songbird Haven, 3 min from town, full house, 3 bedroom, 2 bath
Freedom Farm

Freedom Farm

Middlebury
Stay at this vacation home in Middlebury. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Meadow Valley Golf Club and Riverbend ...
Freedom Farm
Kayaks | Relax by River | 10 Min to Shipshewana |

Kayaks | Relax by River | 10 Min to Shipshewana |

Howe
Stay at this vacation home in Howe. Enjoy free WiFi, a garden, and patios. Popular attractions Green Valley Golf & Health Club and North Park are located ...
Kayaks | Relax by River | 10 Min to Shipshewana |
The Cozy Cottage

The Cozy Cottage

Nappanee
Stay at this vacation home in Nappanee. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Derksen Farm & Wetlands and McCormick Creek ...
The Cozy Cottage
Cozy Home Retreat

Cozy Home Retreat

2 out of 5
Shipshewana
Stay at this vacation home in Shipshewana. Enjoy in-room jetted tubs, an in-room coffeemaker, and in-room fireplaces. Popular attractions North Park and Blue ...
Cozy Home Retreat
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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.

Middlebury Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Middlebury vacation homes are the perfect way for you to wing it.

Holiday houses in Middlebury let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Middlebury in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Middlebury adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Middlebury with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Middlebury vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Middlebury Holiday Homes essential information

Accommodation
215 Holiday Homes
Lowest Price
NZ$175
Highest Price
NZ$501
Popular accommodation
Recently renovated country cottage, 2.5 miles from Shipshewana, Live & Love Life on the Lake at Sunset Peak!, Lake Retreat With Hot Tub, Davis Street Shipshewana, Spring Sale ! Songbird Haven, 3 min from town, full house, 3 bedroom, 2 bath, Freedom Farm, Kayaks | Relax by River | 10 Min to Shipshewana |, The Cozy Cottage, Cozy Home Retreat

Top trending hotels in Middlebury

Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

2.5 out of 5
105 Crystal Heights Blvd, Middlebury, IN
Fully refundableReserve now, pay when you stay
The price is NZ$175 per night from 13 Apr to 14 Apr
NZ$175
includes taxes & fees
13 Apr - 14 Apr
Stay at this hotel in Middlebury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Hampton Inn & Suites Middlebury
Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

3.5 out of 5
240 Hwy 20, Middlebury, IN
The price is NZ$229 per night from 2 Apr to 3 Apr
NZ$229
includes taxes & fees
2 Apr - 3 Apr
Stay at this 3.5-star business-friendly hotel in Middlebury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Essenhaus Inn & Conference Center
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Middlebury
Stay at this vacation home in Middlebury. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Brokesha Lake and Stone Lake are located ...
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
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Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

2 out of 5
Middlebury
The price is NZ$255 per night from 2 Apr to 3 Apr
NZ$255
includes taxes & fees
2 Apr - 3 Apr
Stay at this cottage in Middlebury. Enjoy free WiFi, a garden, and patios. Popular attractions East Lake and Hunter Lake are located nearby.
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
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See all available properties in Middlebury
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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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^Subject to availability and chosen travel dates.