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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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
The price is NT$5,134
NT$9,661 total
includes taxes & fees
Aug 31 - Sep 1
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 NT$4,809
NT$5,713 total
includes taxes & fees
Sep 10 - Sep 11
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
The price is NT$4,731
NT$9,799 total
includes taxes & fees
Sep 2 - Sep 3
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
The price is NT$5,754
NT$11,272 total
includes taxes & fees
Sep 10 - Sep 11
Hidden Log Cabin Hot Tub Ping Pong Family
A spacious living room with a wooden dining table, chairs, a television, and a large window with curtains.

5. Lake House Shallow Sandy Kayaks Family Fun

Lake House Shallow Sandy Kayaks Family Fun
2.0 star property
Shipshewana
The price is NT$4,679
NT$11,490 total
includes taxes & fees
Sep 13 - Sep 14
Lake House Shallow Sandy Kayaks Family Fun
A two-story house with a deck, large windows, and a white exterior.

6. Lakefront Michigan Cottage - Deck, Grill & Kayaks!

Lakefront Michigan Cottage - Deck, Grill & Kayaks!
3.0 star property
Sturgis
The price is NT$6,292
NT$14,870 total
includes taxes & fees
Sep 2 - Sep 3
Lakefront Michigan Cottage - Deck, Grill & Kayaks!
A wooden interior with a staircase, a dining area, and a living room.

7. Secluded Shipshewana Log Cabin In the Woods

Secluded Shipshewana Log Cabin In the Woods
2.0 star property
Shipshewana
The price is NT$5,814
NT$10,147 total
includes taxes & fees
Sep 20 - Sep 21
Secluded Shipshewana Log Cabin In the Woods
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a dining area with a wooden table and black chairs.

8. Relaxing Riverside 10 Minutes to Shipshewana

Relaxing Riverside 10 Minutes to Shipshewana
2.0 star property
Howe
The price is NT$3,767
NT$7,794 total
includes taxes & fees
Aug 31 - Sep 1
Relaxing Riverside 10 Minutes to Shipshewana
A living room with a grand piano, two sofas, a glass coffee table, and a patterned rug.

9. Hot Tub The Strong Retreat Fire Pit 3BR

Hot Tub The Strong Retreat Fire Pit 3BR
2.0 star property
Elkhart
The price is NT$4,220
NT$9,631 total
includes taxes & fees
Sep 1 - Sep 2
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 NT$6,008
NT$9,033 total
includes taxes & fees
Sep 9 - Sep 10
Pet-friendly Cassoplis Cabin, Close to Parks!
A spacious kitchen area with a stone countertop, wooden cabinets, and various appliances including coffee makers and a refrigerator.

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

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
Cassopolis
The price is NT$6,008
NT$8,418 total
includes taxes & fees
Sep 9 - Sep 10
Cassopolis Cabin, Little Fish Lake On-site!
A spacious kitchen with a stone countertop, wooden cabinets, and modern appliances.

12. Cozy Cassopolis Cabin, Near Parks & Golfing!

Cozy Cassopolis Cabin, Near Parks & Golfing!
3.0 star property
Cassopolis
The price is NT$6,008
NT$9,033 total
includes taxes & fees
Sep 9 - Sep 10
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

Der Ruhe Blatz Motel

Der Ruhe Blatz Motel

8/10 Good
"Room was small by todays standards, but was very clean. The AC/heating system was unable to modulate the temperature evenly, but did keep up with outside temperature."
Charles 1-night trip
Posted 5 hours ago
Der Ruhe Blatz Motel

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 Trout 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.