Photo by Ann Sair

Middlebury Holiday Rentals

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Holiday Rentals in Middlebury

The Back Porch Haven Stay in Amish Country yet close to Notre Dame
10.0 out of 10, Exceptional, 4 reviews
"The place was very retro. We enjoyed our stay. Nice place to stay and lay your head. Very clean and accommodating."
The price is NZ$542
per night
26 Jun - 27 Jun
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, 5 reviews
"Loved sitting on the deck, watching the boats & fishermen, sun coming up & going down. Loved the rise & shine donut’s, close to the Shipshewana Flea Market, just an an all around excellent time"
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
10.0 out of 10, Exceptional, 35 reviews
"Loved it!"
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
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Recently renovated country cottage, 2.5 miles from Shipshewana
10.0 out of 10, Exceptional, 187 reviews
"Super clean and organized. Everything that was listed was there. We didn’t need anything that wasn’t there. The only suggestion I could make would be a fire pit in the back. Friday night out on the back patio was great with the stars out."
The price is NZ$300
per night
9 Jun - 10 Jun
Recently renovated country cottage, 2.5 miles from Shipshewana
Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi
10.0 out of 10, Exceptional, 59 reviews
"This was the perfect location to come back to after day trips to Shipshewana. It was very cute, comfortable and cozy. Our favorite part was the hot tub at night overlooking the peaceful and serene lake. We really enjoyed our stay."
Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi
Cozy ‘Haven of Rest’ Home w/ Amish Country Views!
10.0 out of 10, Exceptional, 42 reviews
"Idyllic. The owners were so helpful and friendly. Everything we needed was already there...and then some!!! Soooo close to everything and yet it fell so far removed from the busyness. Would love to come again."
Cozy ‘Haven of Rest’ Home w/ Amish Country Views!
Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, 112 reviews
"Absolutely amazing place, very clean and quiet. Very well furnished especially in the kitchen. Everything you need to cook!"
The price is NZ$292
per night
17 Jun - 18 Jun
Charming farmhouse in peaceful countryside
Cozy Amish Country Cabin on Shipshewana Lake!
9.8 out of 10, Exceptional, 98 reviews
"We enjoyed our stay in the Cozy Amish Cabin. The cabin was very clean and the owners were easy to contact and great to deal with. The weather was unseasonably warm and we enjoyed several hours on the deck, taking in the view and the sunshine. Distance to Shipshewana and local businesses is only a few miles, easy to get to shop/eat and at the same time relax in the quiet of the lake cabin! We have stayed at several VRBO’s and this was the first one where after our stay the owner sent a message...
Cozy Amish Country Cabin on Shipshewana Lake!
Live & Love Life on the Lake!
9.6 out of 10, Exceptional, 21 reviews
"We loved the small lake and also…what do you use on your towels? We want to get that!! The cottage is very comfy and loved all the ceiling fans as well."
The price is NZ$463
per night
5 Jun - 6 Jun
Live & Love Life on the Lake!
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
9.8 out of 10, Exceptional, 12 reviews
"Very accommodating, quick responses to questions. Would definitely book again."
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
Vacation at Garver Lake ~ Private Beach For Your Enjoyment!
8.2 out of 10, Very good, 60 reviews
"The cottage was wonderful!"
Vacation at Garver Lake ~ Private Beach For Your Enjoyment!
Carefree Cottage on the Lake
10.0 out of 10, Exceptional, 154 reviews
"Clean and neatly appointed. All the comforts of home. The neighbors stood out ... everyone waves, everyone smiles, kind of made us fall in love with Michigan. Lake life, seems like it really is the best life. Thank you for sharing your home with us."
Carefree Cottage on the Lake
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.
9.4 out of 10, Exceptional, 19 reviews
"We were looking for a small place near the lake for our small family (myself, wife and daughter). Clean, simple and on point with the description in the listing. Nice touches and some upgrades for an older cottage. It’s all we needed and very convenient to Oakwood Resort and the water. Would book again. Thanks!"
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.
Secluded Riverside Log Home in Southern Michigan
10.0 out of 10, Exceptional, 64 reviews
"There was 6 of us we were celebrating Mikes 60th Birthday. We decided to get out of Ohio and do something different so we found this place. We loved it it was beautiful and had a blast and will definitely coming back soo . The owner was very nice man, I would definitely recommend this place to all my friends and family. I give it 5 stars plus cant wait to go back. Mike & Donna"
Secluded Riverside Log Home in Southern Michigan
Shipshewana Guest House with Fire Pit!
10.0 out of 10, Exceptional, 23 reviews
"We loved our stay at this property. It was a great country setting and very comfortable. The furniture was like new and very comfortable. Many extras like coffee and tea. They provided soaps, shampoo, and plenty of bath towels and wash cloths. The owner checked on us to make sure we were happy with everything and wanted to know if we needed anything. This house is very convenient to all of the attractions and shopping in Shipshewana. You can't go wrong staying here. I would highly recommend this...
Shipshewana Guest House with Fire Pit!
Charming Lake Cottage! Close to Shipshewana, Clean Lake, Boat Rentals
9.8 out of 10, Exceptional, 30 reviews
"This was the perfect home base for our weekend visiting friends nearby. Cute, clean, well equipped, it was just as advertised."
Charming Lake Cottage! Close to Shipshewana, Clean Lake, Boat Rentals
Beautiful Waterfront Home on Baugo Bay
10.0 out of 10, Exceptional, 21 reviews
"We only stayed one night, good location, thanks for good communication as well."
The price is NZ$1,050
per night
17 Jun - 18 Jun
Beautiful Waterfront Home on Baugo Bay
Emma's Place
10.0 out of 10, Exceptional, 26 reviews
"Overnight stay to be able to attend Ship Chic in Shipshewana. Needed a place with 4 bedrooms for 4 adult females. Emma’s place fit the bill. Great communication, adorable house. Only issue was garage next door had roofers starting at 7:30 am and property owner has no control over that. We’re hoping to travel up that way again and would love to have a repeat stay at Emma’s Place"
The price is NZ$507
per night
6 Jun - 7 Jun
Emma's Place
Rocky River Resort
10.0 out of 10, Exceptional, 1 review
"Beautiful and quiet property! A family member got married at Gable Hill and the property was so close to the venue. Rooms were comfortable, plenty of linens and towels. We all enjoyed our stay."
Rocky River Resort
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
10.0 out of 10, Exceptional, 97 reviews
"We loved the hot tub, the porch and the cabin. We loved venturing to Goshen and Elkhart and visiting the towns. There was a coffee table with lighting above that was perfect for our puzzle! We were looking for an isolated cabin, and this is not that, but it was very nice and the beds were super comfy."
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
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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.

Other types of properties in Middlebury you may be interested in

Essenhaus Inn & Conference Center
3.5 star property
9.8 out of 10, Exceptional, 925 reviews
"Das Essenhaus us a wonderful place to stay. The room are beautiful and spacious, the staff is friendly, the grounds are gorgeous!"
The price is NZ$252
per night
16 Jun - 17 Jun
Essenhaus Inn & Conference Center
Hampton Inn & Suites Middlebury
2.5 star property
8.6 out of 10, Excellent, 1,005 reviews
"Stay was good just don’t try to check in a half hour early it would have been an extra $25."
The price is NZ$184
per night
23 Jun - 24 Jun
Hampton Inn & Suites Middlebury
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, 5 reviews
"Loved sitting on the deck, watching the boats & fishermen, sun coming up & going down. Loved the rise & shine donut’s, close to the Shipshewana Flea Market, just an an all around excellent time"
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middlebury holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middlebury. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middlebury. Seeing all the best attractions is bound to make you fall in love with Middlebury. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middlebury short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Deutsch Kase Haus, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Middlebury has a good selection of restaurants. Make sure you have time to check out the shopping and gardens during your trip.

What are some of the best holiday rentals that Middlebury has to offer?

Recently renovated country cottage, 2.5 miles from Shipshewana: This holiday home rental outside of Middlebury is located in the city centre, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a private garden and a selection of games.

How many holiday rentals will I find in Middlebury?

With 15 Expedia holiday rentals, you're guaranteed to find just the right place for your Middlebury stay.

What can I see and do in Middlebury?

While exploring the area, visit family-friendly sights like Deutsch Kase Haus, or get outside and enjoy nature at Wellfield Botanic Gardens. In the wider area, you’ll find Dutch Creek Farm Animal Park and Blue Gate Performing Arts Center.

What are holiday rentals like in Middlebury?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlebury. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a small group gathering.

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