Photo by Ann Sair

Middlebury Holiday Rentals

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Holiday Rentals in Middlebury

Smart TV, books
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
10.0 out of 10, Exceptional, (4)
"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$535
per night
29 May - 30 May
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Property grounds
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
10.0 out of 10, Exceptional, (35)
"Loved it!"
The price is NZ$427
per night
29 May - 30 May
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Property grounds
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, (4)
"The picture do not do this place justice. Absolutely gorgeous cottage and Absolutely the cleanest place ive ever stayed. The stairs are not as intimidating as they seem and the water is so clear you can see the fish swim from up on the deck. Stunning Lake and Stunning views off of any deck. I got ot meet Ryan as I extended my stay and neither of us had done it before but he was super helpful and when the code changed back and i got locked out , I texted Ryan and he was there within 10 minutes...
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
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Exterior
Recently renovated country cottage, 2.5 miles from Shipshewana
10.0 out of 10, Exceptional, (185)
"Short stay but cozy."
The price is NZ$305
per night
30 May - 31 May
Recently renovated country cottage, 2.5 miles from Shipshewana
Fridge, microwave, stovetop, coffee/tea maker
Cozy ‘Haven of Rest’ Home w/ Amish Country Views!
10.0 out of 10, Exceptional, (42)
"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!
Pool
Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (111)
"Absolutely amazing place, very clean and quiet. Very well furnished especially in the kitchen. Everything you need to cook!"
Charming farmhouse in peaceful countryside
Fridge, microwave, stovetop, dishwasher
Cozy Amish Country Cabin on Shipshewana Lake!
9.8 out of 10, Exceptional, (97)
"The only thing that didn't work was the electric fireplace downstairs, everything else was great. They even let me check in early which was nice. I would def stay again. Thanks."
Cozy Amish Country Cabin on Shipshewana Lake!
Fridge, microwave, oven, stovetop
Vacation at Garver Lake ~ Private Beach For Your Enjoyment!
8.2 out of 10, Very good, (60)
"The cottage was wonderful!"
Vacation at Garver Lake ~ Private Beach For Your Enjoyment!
Property grounds
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
9.8 out of 10, Exceptional, (12)
"Very accommodating, quick responses to questions. Would definitely book again."
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
Pool
Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi
10.0 out of 10, Exceptional, (59)
"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
Fridge, microwave, oven, stovetop
Welcoming Grace College parents, fall weddings, traveling for work, or anything
9.8 out of 10, Exceptional, (9)
"Fantastic hosts! The home was super clean and had all the amenities we needed. It was a perfect location our events in Warsaw. We hope to be back next year!"
Welcoming Grace College parents, fall weddings, traveling for work, or anything
Fridge, oven, stovetop, coffee/tea maker
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.
9.4 out of 10, Exceptional, (19)
"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.
Property grounds
Beautiful Waterfront Home on Baugo Bay
10.0 out of 10, Exceptional, (21)
"We only stayed one night, good location, thanks for good communication as well."
The price is NZ$1,076
per night
27 May - 28 May
Beautiful Waterfront Home on Baugo Bay
Fridge, microwave, oven, dishwasher
Cozy Lake House On The Channel With Access To 5 Lakes!
9.8 out of 10, Exceptional, (18)
"Very nice inside and out, went for TOC with a couple of friends our stay there was perfect, would definitely recommend this lake house."
The price is NZ$420
per night
28 May - 29 May
Cozy Lake House On The Channel With Access To 5 Lakes!
Property grounds
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
10.0 out of 10, Exceptional, (97)
"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!
Property grounds
Carefree Cottage on the Lake
10.0 out of 10, Exceptional, (154)
"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
Beach
Live & Love Life on the Lake!
9.6 out of 10, Exceptional, (20)
"Looking for a special quiet place to spend time with my daughters for a mother's day getaway, I chose the perfect spot. It was everything I hoped for, comfortable, cozy and right on the water. Perfect!"
The price is NZ$525
per night
3 Jun - 4 Jun
Live & Love Life on the Lake!
Fridge, microwave, oven, stovetop
Emma's Place
10.0 out of 10, Exceptional, (26)
"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$514
per night
28 May - 29 May
Emma's Place
Fridge, microwave, stovetop, coffee/tea maker
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
9.8 out of 10, Exceptional, (16)
"Loved our stay at this cozy farmhouse. It was perfect for our family and our dog. Huge, fully stocked kitchen, washer and dryer and three full bedrooms. All in the scenic country of Indiana,"
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
Exterior
Comfy & Cozy Lakefront Cottage
10.0 out of 10, Exceptional, (43)
"Absolutely wonderful, serene place to stay. Perfect little cottage with all the necessary amenities and a breathtaking view of the lake Didn't want to leave and want to come back again!!"
Comfy & Cozy Lakefront Cottage
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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

Courtyard
Essenhaus Inn & Conference Center
3.5 star property
9.8 out of 10, Exceptional, (913)
"Everything about our stay was lovely. Beautiful room, breakfast was great, went for long walks on the property. Front desk staff were helpful and very nice. Restaurant was also very good. We will be back."
The price is NZ$292
per night
30 May - 31 May
Essenhaus Inn & Conference Center
Restaurant
Hampton Inn & Suites Middlebury
2.5 star property
8.6 out of 10, Excellent, (1001)
"Z"
The price is NZ$186
per night
23 Jun - 24 Jun
Hampton Inn & Suites Middlebury
Property grounds
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, (4)
"The picture do not do this place justice. Absolutely gorgeous cottage and Absolutely the cleanest place ive ever stayed. The stairs are not as intimidating as they seem and the water is so clear you can see the fish swim from up on the deck. Stunning Lake and Stunning views off of any deck. I got ot meet Ryan as I extended my stay and neither of us had done it before but he was super helpful and when the code changed back and i got locked out , I texted Ryan and he was there within 10 minutes...
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.

Recent reviews of Middlebury properties
Expedia verified reviews