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31 Dec - 1 Jan
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1 Jan - 2 Jan
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2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Middlebury holiday rentals

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

The Wellington Cottage

The Wellington Cottage
3.0 star property
Middlebury
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
House | 2 bedrooms
Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is ฿3,532
฿7,778 total
includes taxes & fees
8 Jan - 9 Jan 2026
Farm Country Amish Country Newly Renovated
House (2 Bedrooms) | Interior
Cassopolis Cabin, Little Fish Lake On-site!

Cassopolis Cabin, Little Fish Lake On-site!

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
Cassopolis
The price is ฿4,624
฿7,859 total
includes taxes & fees
1 Jan - 2 Jan 2026
Cassopolis Cabin, Little Fish Lake On-site!
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

avid Hotels Elkhart North by IHG

avid Hotels Elkhart North by IHG

10/10 Excellent
"Helpful, kind staff."
Joanne 1-night trip
Posted 2 days ago
avid Hotels Elkhart North by IHG

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.

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.