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Middlebury Vacation Rentals

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Middlebury vacation rentals

Family Cottage, 3 Bedrooms, Non Smoking, Lake View | Lake view
The Wellington Cottage

Cottage in Middlebury

The Wellington Cottage
3.0 star property
10.0 out of 10, Exceptional, (6)
"It had everything we needed was off the beaten path, we swam in the water and used the paddle boat, nice and relaxing"
United States
Susan
The Wellington Cottage
Property grounds
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Cottage in Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
2.0 star property
10.0 out of 10, Exceptional, (42)
"Very nice place a little into the countryside. Will definitely stay again next time I’m in the area."
United States
Brad
The price is ￥17,956
￥22,554 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Smart TV, books
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Vacation Home in Middlebury

The Back Porch Haven Stay in Amish Country yet close to Notre Dame
10.0 out of 10, Exceptional, (26)
"Came up for a wedding and had a wonderful time with my friends. Thank you for being such great hosts! "
United States
Thomas B.
The price is ￥24,171
￥54,562 total
includes taxes & fees
Jan 26 - Jan 27, 2026
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
House | 2 bedrooms
Farm Country Amish Country Newly Renovated

Vacation Home in Middlebury

Farm Country Amish Country Newly Renovated
2.0 star property
The price is ￥22,831
￥44,277 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Farm Country Amish Country Newly Renovated
Property grounds
Relax and unwind at the Cozy Cabin on Heaton Lake.

Cabin in Elkhart

Relax and unwind at the Cozy Cabin on Heaton Lake.
2.0 star property
10.0 out of 10, Exceptional, (24)
"Excellent communication...respected privacy...clean...relaxing !!"
United States
Barry R.
The price is ￥15,458
￥28,569 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Relax and unwind at the Cozy Cabin on Heaton Lake.
Outdoor dining
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!

Cabin in Marcellus

Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
9.0 out of 10, Wonderful, (14)
"We were looking for a place off the beaten path with plenty of privacy and this locstion provided both. The hosts were fantastic and we had a great time. "
United States
Trevor W.
The price is ￥13,255
￥18,728 total
includes taxes & fees
Dec 27 - Dec 28
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
Outdoor dining
Live & Love Life on the Lake at Sunset Cottage!

Cottage in Howe

Live & Love Life on the Lake at Sunset Cottage!
9.6 out of 10, Exceptional, (56)
"Nice little cottage. Clean. Everything we needed and great location. "
United States
Laurie S.
The price is ￥15,458
￥38,426 total
includes taxes & fees
Dec 28 - Dec 29
Live & Love Life on the Lake at Sunset Cottage!
Exterior detail
Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet

Cottage in Vandalia

Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet
10.0 out of 10, Exceptional, (67)
"We loved it, in town for our sons wedding & coincidentally they stayed at “The Grain Binn”which was a dream as well, ours was so cozy and quaint clean and accommodating, it had all the creature comforts and so much more, we will definitely be back & tell our friends all about the beauty & charm of your cottages"
United States
Victoria Z.
The price is ￥21,079
￥35,616 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet
Private kitchen
The Gemini

Vacation Home in Elkhart

The Gemini
9.0 out of 10, Wonderful, (12)
"We have friends that live close. This was the perfect location for a weekend visit."
United States
Rhonda R.
The price is ￥18,128
￥22,739 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Gemini
House (2 Bedrooms) | Interior
Cassopolis Cabin, Little Fish Lake On-site!

Cottage in Cassopolis

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
The price is ￥22,953
￥39,009 total
includes taxes & fees
Dec 28 - Dec 29
Cassopolis Cabin, Little Fish Lake On-site!
Exterior
Winding Creek Cabins

Cabin in Marcellus

Winding Creek Cabins
10.0 out of 10, Exceptional, (8)
"Very clean and comfortable. Great view of nature"
United States
Keith M.
The price is ￥27,965
￥37,294 total
includes taxes & fees
Dec 27 - Dec 28
Winding Creek Cabins
Microwave, oven, stovetop
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Cottage in Syracuse

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
9.8 out of 10, Exceptional, (7)
"Great clean little cabin by the lake. Hot tub and outdoor area is nice! Very private with a view of the water on the porch. "
United States
Ty M.
The price is ￥20,116
￥40,694 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Fridge, microwave, oven, dishwasher
Cozy Lake House On The Channel With Access To 5 Lakes!

Vacation Home in Wolcottville

Cozy Lake House On The Channel With Access To 5 Lakes!
9.6 out of 10, Exceptional, (41)
"Nice Property, affordable, pice and Nice Location. "
United States
Dimple N.
The price is ￥23,889
￥43,633 total
includes taxes & fees
Dec 29 - Dec 30
Cozy Lake House On The Channel With Access To 5 Lakes!
Interior
Welcome to our Home in Ligonier

Vacation Home in Ligonier

Welcome to our Home in Ligonier
2.0 star property
10.0 out of 10, Exceptional, (2)
"This is our third time renting this property. The hosts are awesome and pay attention to detail. Couldn't be happier with our stay!"
United States
Jeremiah A.
The price is ￥17,956
￥37,948 total
includes taxes & fees
Dec 27 - Dec 28
Welcome to our Home in Ligonier
Terrace/patio
Charming farmhouse in peaceful countryside

Vacation Home in Nappanee

Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (165)
"The farmhouse is wonderfully updated and is quiet and comfortable. "
United States
Brent L.
The price is ￥15,458
￥24,894 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Charming farmhouse in peaceful countryside
Property grounds
Cottages on Sand Lake - The Cozy Cottage

Vacation Home in Sturgis

Cottages on Sand Lake - The Cozy Cottage
9.2 out of 10, Wonderful, (23)
"Nice little spot with great views of the lake. Kept us warm when the weather was stormy, and the kayaks were fun to take out when the sun came out."
United States
Marissa T.
The price is ￥18,206
￥39,285 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cottages on Sand Lake - The Cozy Cottage
Fridge, microwave, oven, stovetop
Emma's Place

Vacation Home in LaGrange

Emma's Place
9.8 out of 10, Exceptional, (58)
"Enjoyed our stay! Would definitely stay here again."
United States
James S.
The price is ￥23,391
￥52,723 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Emma's Place
Microwave, stovetop, coffee/tea maker, toaster
Little Luxe Retreat #7 | Tiny Home + Fire Table

Vacation Home in Shipshewana

Little Luxe Retreat #7 | Tiny Home + Fire Table
2.0 star property
10.0 out of 10, Exceptional, (2)
"Very enjoyable stay."
United States
June P.
The price is ￥18,034
￥47,135 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Little Luxe Retreat #7 | Tiny Home + Fire Table
House | 2 bedrooms
Relaxing Riverside 10 Minutes to Shipshewana

Vacation Home in Howe

Relaxing Riverside 10 Minutes to Shipshewana
2.0 star property
The price is ￥18,885
￥37,231 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Relaxing Riverside 10 Minutes to Shipshewana
Dining
Woodside Retreat in the Heart of Amish Country

Vacation Home in Nappanee

Woodside Retreat in the Heart of Amish Country
10.0 out of 10, Exceptional, (11)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
United States
VICKI
The price is ￥17,933
￥30,868 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Woodside Retreat in the Heart of Amish Country
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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Top Middlebury Hotel Reviews

Blue Gate Garden Inn

Blue Gate Garden Inn

10/10 Excellent
"Yes, room was spotless. Front desk staff exceptional with questions we had. Breakfast staff pleasant and friendly. "
Susan 1-night trip
Posted 4 days ago
Blue Gate Garden Inn

Find out more about Middlebury

Search for holiday rentals in Middlebury on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlebury using one of the methods below:

  • View our selection of featured holiday rentals in Middlebury
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  • Enter your travel dates to view the best deals on holiday rentals in Middlebury while they last

Look no further and take a look at our great range of rental properties in Middlebury!

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?

The Back Porch Haven Stay in Amish Country yet close to Notre Dame: Visitors like this Middlebury vacation home rental. It is located in a rural location and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Some other homes for rent in Middlebury include HOT TUB | Beautiful Backyard Oasis|Newly Renovated and Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame..

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?

Stone Lake and Trout Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Deutsch Kase Haus. While here, Middlebury Community Historical and Meadow Valley Golf Club are other places worth a visit.

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.