A log cabin with red shutters and a small porch.

Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Middlebury vacation rentals

Terrace/patio

The Wellington Cottage

The Wellington Cottage
3.0 star property
Middlebury
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful views "
United States
Darwin
The price is P11,035
P13,043 total
includes taxes & fees
Jul 19 - Jul 20
The Wellington Cottage
2 bedrooms

Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is P9,386
P19,409 total
includes taxes & fees
Jul 6 - Jul 7
Farm Country Amish Country Newly Renovated
3 bedrooms

Amish Country Getaway Farm Views Fire Pit

Amish Country Getaway Farm Views Fire Pit
2.0 star property
Middlebury
The price is P9,386
P18,285 total
includes taxes & fees
Jul 6 - Jul 7
Amish Country Getaway Farm Views Fire Pit
3 bedrooms

Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
The price is P13,342
P24,414 total
includes taxes & fees
Jul 8 - Jul 9
Hidden Log Cabin Hot Tub Ping Pong Family
2 bedrooms

Relaxing Riverside 10 Minutes to Shipshewana

Relaxing Riverside 10 Minutes to Shipshewana
2.0 star property
Howe
The price is P9,446
P17,708 total
includes taxes & fees
Jul 6 - Jul 7
Relaxing Riverside 10 Minutes to Shipshewana
Interior

Lakefront Michigan Cottage - Deck, Grill & Kayaks!

Lakefront Michigan Cottage - Deck, Grill & Kayaks!
3.0 star property
Sturgis
The price is P12,224
P28,888 total
includes taxes & fees
Jul 15 - Jul 16
Lakefront Michigan Cottage - Deck, Grill & Kayaks!
3 bedrooms

Lake House Shallow Sandy Kayaks Family Fun

Lake House Shallow Sandy Kayaks Family Fun
2.0 star property
Shipshewana
The price is P20,229
P35,343 total
includes taxes & fees
Jul 6 - Jul 7
Lake House Shallow Sandy Kayaks Family Fun
2 bedrooms

Lake Front Cottage Kayaks Game Table Fun

Lake Front Cottage Kayaks Game Table Fun
2.0 star property
Shipshewana
10.0 out of 10, Exceptional, (1 review)
"Loved the cottage! Everything was as stated in the property description and the cottage is decorated very nicely and very clean. Unfortunately, there was severe weather and we had to delay our trip a day. When I asked if we'd be able to get a refund for one day, I got no response from the property manager. However, we accidentally took a book from the cottage and when we texted Todd, he responded immediately and was very helpful in how to return the book. The weather did not cooperate for...
United States
Ron
The price is P14,111
P23,491 total
includes taxes & fees
Jul 20 - Jul 21
Lake Front Cottage Kayaks Game Table Fun
3 bedrooms

Hot Tub The Strong Retreat Fire Pit 3BR

Hot Tub The Strong Retreat Fire Pit 3BR
2.0 star property
Elkhart
The price is P18,717
P30,165 total
includes taxes & fees
Jul 8 - Jul 9
Hot Tub The Strong Retreat Fire Pit 3BR
2 bedrooms

Secluded Shipshewana Log Cabin In the Woods

Secluded Shipshewana Log Cabin In the Woods
2.0 star property
Shipshewana
The price is P16,932
P26,317 total
includes taxes & fees
Jul 29 - Jul 30
Secluded Shipshewana Log Cabin In the Woods
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

Tru by Hilton Elkhart, IN

Tru by Hilton Elkhart, IN

10/10 Excellent
"Staff was amazing and accommodating. Room was really nice. Bathroom was okay. Lobby is amazing. Location is amazing."
Craig 1-night trip
Posted 11 hours ago
Tru by Hilton Elkhart, IN

Find out more about Middlebury

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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.

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 Hunter Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Deutsch Kase Haus. While here, Middlebury Public Library and Middlebury Community Historical 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.