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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middlebury vacation rentals

A kitchen with light green cabinets, a white island with stools, a stainless steel refrigerator, and a 'Coffee' sign on the wall.

1. Amish Country Getaway Farm Views Fire Pit

Amish Country Getaway Farm Views Fire Pit
2.0 star property
Middlebury
Amish Country Getaway Farm Views Fire Pit
A waterfront view with an American flag, a boat, and a sunset.

2. The Wellington Cottage

The Wellington Cottage
3.0 star property
Middlebury
10.0 out of 10, Exceptional, (9 reviews)
"Easy 10/10 recommendation Perfect place for peace"
United States
Bonala
The price is P6,136
P7,417 total
includes taxes & fees
Nov 1 - Nov 2
The Wellington Cottage
A kitchen with a double sink, light-colored cabinets, and a refrigerator.

3. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
Farm Country Amish Country Newly Renovated
A log cabin interior with a dining area, a living room, a staircase, and a coffee bar.

4. Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
Hidden Log Cabin Hot Tub Ping Pong Family
A cozy seating area with wicker chairs and a teal rug, a 'Welcome to our Lake House' sign, and nautical decorations.

5. 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 P7,665
P16,454 total
includes taxes & fees
Oct 5 - Oct 6
Lake Front Cottage Kayaks Game Table Fun
A spacious kitchen area with a stone countertop, wooden cabinets, and various appliances including coffee makers and a refrigerator.

6. Cassopolis Cabin, Little Fish Lake On-site!

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
Cassopolis
The price is P11,885
P16,654 total
includes taxes & fees
Oct 8 - Oct 9
Cassopolis Cabin, Little Fish Lake On-site!
A spacious living room with a wooden dining table, chairs, a television, and a large window with curtains.

7. Lake House Shallow Sandy Kayaks Family Fun

Lake House Shallow Sandy Kayaks Family Fun
2.0 star property
Shipshewana
The price is P11,337
P25,770 total
includes taxes & fees
Oct 14 - Oct 15
Lake House Shallow Sandy Kayaks Family Fun
A wooden interior with a staircase, a dining area, and a living room.

8. Secluded Shipshewana Log Cabin In the Woods

Secluded Shipshewana Log Cabin In the Woods
2.0 star property
Shipshewana
The price is P11,577
P20,528 total
includes taxes & fees
Oct 21 - Oct 22
Secluded Shipshewana Log Cabin In the Woods
A living room with a fireplace, a bookshelf, and a large mirror.

9. Hot Tub The Strong Retreat Fire Pit 3BR

Hot Tub The Strong Retreat Fire Pit 3BR
2.0 star property
Elkhart
Hot Tub The Strong Retreat Fire Pit 3BR
A spacious indoor area with high ceilings, large windows, and multiple tables.

10. Pet-friendly Cassoplis Cabin, Close to Parks!

Pet-friendly Cassoplis Cabin, Close to Parks!
3.0 star property
Cassopolis
The price is P11,885
P17,870 total
includes taxes & fees
Oct 8 - Oct 9
Pet-friendly Cassoplis Cabin, Close to Parks!
A red cabin with a wooden deck and a staircase leading to a window.

11. Cozy Cassopolis Cabin, Near Parks & Golfing!

Cozy Cassopolis Cabin, Near Parks & Golfing!
3.0 star property
Cassopolis
The price is P11,885
P17,870 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Cassopolis Cabin, Near Parks & Golfing!
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

Van Buren Hotel

Van Buren Hotel

10/10 Excellent
"Our key card didn’t work for the gym but it worked for the pool as well as our room. Staff was extremely helpful and kind. Breakfast was top 10 for hotels we’ve stayed at in the past. Mostly amish town, very quiet and peaceful and only a 10 min drive to the Michigan boarder."
Bruce 2-night trip
Posted 15 hours ago
Van Buren Hotel

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:

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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 17 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 Brokesha Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Deutsch Kase Haus. While here, Meadow Valley Golf Club and Middlebury Public Library 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.