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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)
"The place was very retro. We enjoyed our stay. Nice place to stay and lay your head. Very clean and accommodating."
The price is AU$464
per night
13 May - 14 May
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
10.0 out of 10, Exceptional, (35)
"Loved it!"
The price is AU$452
per night
29 May - 30 May
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Recently renovated country cottage, 2.5 miles from Shipshewana
10.0 out of 10, Exceptional, (179)
"This had a out in the country feel, but was close to town. It was clean, and had a view of the Amish buggies going by. We enjoyed our stay and would rate it 5 stars."
The price is AU$283
per night
18 May - 19 May
Recently renovated country cottage, 2.5 miles from Shipshewana
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Cozy ‘Haven of Rest’ Home w/ Amish Country Views!
10.0 out of 10, Exceptional, (41)
"My family and I had the opportunity to stay at this location. It was perfect. The owners of the property were delightful and really enjoyed the connection we made. You won’t regret staying at this property. Such a beautiful site."
Cozy ‘Haven of Rest’ Home w/ Amish Country Views!
Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi
10.0 out of 10, Exceptional, (57)
"The cabin was as described. Very clean, quiet and comfortable. We even sat out in the hot tub after dark and it was the perfect end to our day of driving and visiting Shipshewana."
Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi
Emma's Place
10.0 out of 10, Exceptional, (25)
"We had a girls weekend away to enjoy some country music in Shipshewana and celebrate St. Patty’s Day in Legrange. The house was roomy, comfortable, beautiful, and well stocked for all that we needed. The location was perfect and we couldn’t have asked for anything better!"
The price is AU$477
per night
6 June - 7 June
Emma's Place
Carefree Cottage on the Lake
10.0 out of 10, Exceptional, (153)
"Very good experience!"
Carefree Cottage on the Lake
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
10.0 out of 10, Exceptional, (95)
"Beautiful house, clean, great setting. Would recommend."
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
Comfy & Cozy Lakefront Cottage
10.0 out of 10, Exceptional, (41)
"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
Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (110)
"Just a quick trip to the area to visit my relatives and decided to stay here for a second time. We weren’t disappointed! The house was very clean and ready for us. We even ask and received an earlier check in. Michelle continues to be great to work with. If you like the idea of staying in a really nice country cottage on a farm this is the place! Even have your own 4 legged furry greeting party! Dixie is the friendliest and always gentle! She loves attention and greeted us each time we arrived...
Charming farmhouse in peaceful countryside
Davis Street Shipshewana
10.0 out of 10, Exceptional, (44)
"This property was perfect for our girls trip to Shipshewana. Great location, quiet neighborhood, very clean, and the house had every thing we needed. Will definitely stay here again!"
The price is AU$308
per night
1 June - 2 June
Davis Street Shipshewana
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 AU$968
per night
8 May - 9 May
Summer Sizzle! 6-Bed Channel Home!
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 AU$989
per night
13 May - 14 May
Beautiful Waterfront Home on Baugo Bay
Idyllic Lake Cottage on Papakeechie Lake
10.0 out of 10, Exceptional, (23)
"Everything was great! Very clean and cozy place! Thank you!"
Idyllic Lake Cottage on Papakeechie Lake
Couples Hideaway, Private, Coziness, Country, Hygge.
10.0 out of 10, Exceptional, (46)
"Totally Awesome! Place was impressive, secluded and private. Exceeded expectations by a bunch. If I could give 6 stars, I would. This hideaway had everything to make our stay perfect. Dawn had us setup with fresh cinnamon rolls to enjoy from the get go. There is a fire pit , a gazebo with table , grill and trails to follow. The bird feeder was so entertaining from many different birds and the cutest chipmunks. We are hoping to return soon. A great getaway!"
The price is AU$330
per night
13 May - 14 May
Couples Hideaway, Private, Coziness, Country, Hygge.
Newly Remodeled Cabin Steps from Sylvan Lake
10.0 out of 10, Exceptional, (24)
"Nice view looking down at the lake. A comfortable stay overall."
Newly Remodeled Cabin Steps from Sylvan Lake
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!
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
9.8 out of 10, Exceptional, (12)
"Plenty of space and a nice neighborhood. We enjoyed our visit."
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
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 AU$384
per night
14 May - 15 May
Cozy Lake House On The Channel With Access To 5 Lakes!
Live & Love Life on the Lake!
9.6 out of 10, Exceptional, (19)
"This place was perfect. Comfortable beds. Pretty view. Wonderful host. Couldn't of been better. We will definitely stay again!!"
The price is AU$399
per night
9 May - 10 May
Live & Love Life on the Lake!
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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 Holiday Home Travel Info

Other types of properties in Middlebury you may be interested in

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 AU$464
per night
13 May - 14 May
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Essenhaus Inn & Conference Center
3.5 star property
9.8 out of 10, Exceptional, (902)
"The room was great. Had plenty of seating to relax in. Bed was comfortable. Room was clean and very quiet. Continental breakfast was good and there was a nice variety to choose from. Breakfast area was very comfortable with plenty of places to sit and eat or just sit at one of the sofas and enjoy the fireplace. We would definitely stay again."
The price is AU$269
per night
13 May - 14 May
Essenhaus Inn & Conference Center
Farmstead Inn & Conference Center
2.5 star property
9.6 out of 10, Exceptional, (1003)
"We have stayed here a couple of times. Never disappointed!"
The price is AU$256
per night
12 May - 13 May
Farmstead 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.

Everything you need to know about Middlebury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlebury holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middlebury holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlebury. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury holiday rentals we have selected for you start as low as AU$283 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlebury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlebury holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlebury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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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