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Middlebury Vacation Rentals

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Vacation 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 CA $198
CA $451 total
includes taxes & fees
May 30 - May 31
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 CA $179
CA $360 total
includes taxes & fees
May 29 - May 30
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 CA $198
CA $254 total
includes taxes & fees
Jun 3 - Jun 4
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
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
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 CA $682
CA $896 total
includes taxes & fees
May 27 - May 28
Beautiful Waterfront Home on Baugo Bay
Property grounds
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
10.0 out of 10, Exceptional, (96)
"GREAT PLACE TO STAY THE HOT TUB WAS AMAZING!!!"
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
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 CA $205
CA $428 total
includes taxes & fees
Jun 3 - Jun 4
Emma's Place
Property grounds
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
Exterior
Rocky River Resort
10.0 out of 10, Exceptional, (1)
"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
Smart TV
Davis Street Shipshewana
10.0 out of 10, Exceptional, (46)
"The place was very clean and convenient to the Bluegate Theatre venue. Thank you for the accommodations!"
The price is CA $150
CA $280 total
includes taxes & fees
Jun 9 - Jun 10
Davis Street Shipshewana
5 bedrooms, iron/ironing board, free WiFi, bed sheets
Summer Sizzle! 6-Bed Channel Home!
10.0 out of 10, Exceptional, (18)
"Enjoyed 2 weeks of Family time snuggled in during subzero temps and snowstorms. Plenty of space for games, eating, movie nights and napping. Comfortable beds, lots of TV’s and a well-appointed kitchen also made for the perfect stay. Neighborhood is peaceful and private and hostess is extra responsive."
The price is CA $450
CA $1,013 total
includes taxes & fees
May 27 - May 28
Summer Sizzle! 6-Bed Channel Home!
Terrace/patio
Shipshewana Guest House with Fire Pit!
10.0 out of 10, Exceptional, (21)
"Relaxing getaway. Close to town."
Shipshewana Guest House with Fire Pit!
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!
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
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, microwave, oven, dishwasher
Cozy Lake House On The Channel With Access To 5 Lakes!
9.8 out of 10, Exceptional, (17)
"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 CA $205
CA $350 total
includes taxes & fees
Jun 3 - Jun 4
Cozy Lake House On The Channel With Access To 5 Lakes!
Don't see what you're looking for?
See all available properties in Middlebury
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 Vacation Rental Travel Info

Other types of properties in Middlebury you may be interested in

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.
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 CA $198
CA $451 total
includes taxes & fees
May 30 - May 31
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
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 CA $217
CA $243 total
includes taxes & fees
Jun 6 - Jun 7
Essenhaus Inn & Conference Center
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Middlebury?

Yes, you can find vacation rentals in Middlebury near Deutsch Kase Haus, or you can choose a more remote option if you're looking for extra privacy while you relax. Our travelers say Middlebury has a good selection of restaurants. Make sure you have time to check out the shopping and gardens during your trip.

What's the top vacation rental in Middlebury?

Recently renovated country cottage, 2.5 miles from Shipshewana: This vacation home rental outside of Middlebury is located in the city center 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 yard and a selection of games.

How many vacation rentals will I find in Middlebury?

With 15 Expedia vacation rentals, you're sure 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 larger area, you’ll find Dutch Creek Farm Animal Park and Blue Gate Performing Arts Center.

What are vacation rentals like in Middlebury?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Middlebury. Vacation rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family gatherings.

Recent reviews of Middlebury properties
Expedia verified reviews