Photo by Ann Sair

Middlebury Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Middlebury holiday rentals

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 HK$894
HK$1,123 total
includes taxes & fees
25 Dec - 26 Dec
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Exterior
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Holiday 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 HK$1,205
HK$2,738 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
2 bedrooms
Farm Country Amish Country Newly Renovated

Holiday Home in Middlebury

Farm Country Amish Country Newly Renovated
2.0 star property
The price is HK$1,195
HK$2,267 total
includes taxes & fees
8 Jan - 9 Jan 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 HK$777
HK$1,430 total
includes taxes & fees
2 Jan - 3 Jan 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 HK$661
HK$934 total
includes taxes & fees
27 Dec - 28 Dec
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 HK$770
HK$1,914 total
includes taxes & fees
28 Dec - 29 Dec
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 HK$1,155
HK$1,901 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet
Private kitchen
The Gemini

Holiday 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 HK$1,003
HK$1,240 total
includes taxes & fees
9 Jan - 10 Jan 2026
The Gemini
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 HK$1,143
HK$1,943 total
includes taxes & fees
25 Dec - 26 Dec
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 HK$1,393
HK$1,858 total
includes taxes & fees
25 Dec - 26 Dec
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 HK$1,003
HK$2,030 total
includes taxes & fees
28 Dec - 29 Dec
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!

Holiday 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 HK$1,190
HK$2,155 total
includes taxes & fees
28 Dec - 29 Dec
Cozy Lake House On The Channel With Access To 5 Lakes!
Interior
Welcome to our Home in Ligonier

Holiday 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 HK$894
HK$1,890 total
includes taxes & fees
25 Dec - 26 Dec
Welcome to our Home in Ligonier
Terrace/patio
Charming farmhouse in peaceful countryside

Holiday 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 HK$770
HK$1,240 total
includes taxes & fees
13 Jan - 14 Jan 2026
Charming farmhouse in peaceful countryside
Property grounds
Cottages on Sand Lake - The Cozy Cottage

Holiday 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 HK$907
HK$1,957 total
includes taxes & fees
6 Jan - 7 Jan 2026
Cottages on Sand Lake - The Cozy Cottage
Fridge, microwave, oven, stovetop
Emma's Place

Holiday 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 HK$1,167
HK$2,647 total
includes taxes & fees
28 Dec - 29 Dec
Emma's Place
Microwave, stovetop, coffee/tea maker, toaster
Little Luxe Retreat #7 | Tiny Home + Fire Table

Holiday 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 HK$988
HK$2,451 total
includes taxes & fees
25 Dec - 26 Dec
Little Luxe Retreat #7 | Tiny Home + Fire Table
2 bedrooms
Relaxing Riverside 10 Minutes to Shipshewana

Holiday Home in Howe

Relaxing Riverside 10 Minutes to Shipshewana
2.0 star property
The price is HK$930
HK$1,842 total
includes taxes & fees
6 Jan - 7 Jan 2026
Relaxing Riverside 10 Minutes to Shipshewana
Dining
Woodside Retreat in the Heart of Amish Country

Holiday 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 HK$894
HK$1,540 total
includes taxes & fees
30 Dec - 31 Dec
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

La Quinta Inn & Suites by Wyndham Elkhart

La Quinta Inn & Suites by Wyndham Elkhart

10/10 Excellent
"Everything good, and clean I really recommend this hotel"
Yony 1-night trip
Posted 3 days ago
La Quinta Inn & Suites by Wyndham Elkhart

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
  • Use the map to find apartments and other holiday homes in the Middlebury neighbourhood you prefer
  • 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 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?

The Back Porch Haven Stay in Amish Country yet close to Notre Dame: This highly rated holiday home rental in Middlebury is located in a rural location, and has a patio, a selection of games and a BBQ 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 that 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 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?

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 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.