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

Our top choices for Middlebury holiday 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 RM667
RM1,281 total
includes taxes & fees
15 Oct - 16 Oct
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 RM401
RM484 total
includes taxes & fees
1 Nov - 2 Nov
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 RM499
RM1,178 total
includes taxes & fees
6 Oct - 7 Oct
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 RM1,418
RM2,213 total
includes taxes & fees
16 Oct - 17 Oct
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 RM500
RM1,074 total
includes taxes & fees
5 Oct - 6 Oct
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 RM776
RM1,087 total
includes taxes & fees
5 Oct - 6 Oct
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 RM641
RM1,569 total
includes taxes & fees
6 Oct - 7 Oct
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 RM777
RM1,364 total
includes taxes & fees
21 Oct - 22 Oct
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 RM776
RM1,167 total
includes taxes & fees
5 Oct - 6 Oct
Pet-friendly Cassoplis Cabin, Close to Parks!
A spacious indoor area with a long counter, coffee machines, and a refrigerator labeled 'milk & dairy.'

11. Cozy Cassopolis Cabin, Near Parks & Golfing!

Cozy Cassopolis Cabin, Near Parks & Golfing!
3.0 star property
Cassopolis
The price is RM776
RM1,167 total
includes taxes & fees
5 Oct - 6 Oct
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 5 hours ago
Van Buren Hotel

Find out more about Middlebury

Search for holiday rentals in Middlebury on Expedia.co.uk! 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 17 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 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 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.