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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Middlebury vacation rentals

Property grounds

1. Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Middlebury
10.0 out of 10, Exceptional, (69 reviews)
"Excellent place to stay, planning on staying again when we come to visit family. "
United States
Cara B.
The price is AED 569
AED 696 total
includes taxes & fees
27 Sep - 28 Sep
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Outdoor spa tub

2. HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Middlebury
10.0 out of 10, Exceptional, (77 reviews)
"This is a great Property!"
United States
Patrick B.
The price is AED 799
AED 1,403 total
includes taxes & fees
8 Oct - 9 Oct
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Terrace/patio

3. 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 AED 426
AED 512 total
includes taxes & fees
11 Oct - 12 Oct
The Wellington Cottage
Exterior

4. Charming 3-bedroom house located on Main Street in Downtown Middlebury

Charming 3-bedroom house located on Main Street in Downtown Middlebury
Middlebury
9.6 out of 10, Exceptional, (26 reviews)
"Nice clean conveniently located to visit all the area has to offer."
United States
Mary W.
Charming 3-bedroom house located on Main Street in Downtown Middlebury
Outdoor spa tub

5. | Hot Tub | Amish Farm Country | Pergola | Deck |

| Hot Tub | Amish Farm Country | Pergola | Deck |
Middlebury
10.0 out of 10, Exceptional, (103 reviews)
"This was a warm and cozy stay! "
United States
Tim B.
The price is AED 653
AED 1,273 total
includes taxes & fees
24 Sep - 25 Sep
| Hot Tub | Amish Farm Country | Pergola | Deck |
House | 3 bedrooms

6. Amish Country Getaway Farm Views Fire Pit

Amish Country Getaway Farm Views Fire Pit
2.0 star property
Middlebury
The price is AED 479
AED 1,022 total
includes taxes & fees
28 Sep - 29 Sep
Amish Country Getaway Farm Views Fire Pit
Smart TV, books

7. The Back Porch Haven Stay in Amish Country yet close to Notre Dame

The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Middlebury
10.0 out of 10, Exceptional, (34 reviews)
"Loved the house. Clean and comfortable and convenient to shipshewana and goshen."
United States
Dianna D.
The price is AED 520
AED 1,232 total
includes taxes & fees
24 Sep - 25 Sep
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Smart TV, DVD player

8. Hidden Log Cabin | Hot Tub | Ping Pong | Family |

Hidden Log Cabin | Hot Tub | Ping Pong | Family |
Goshen
10.0 out of 10, Exceptional, (16 reviews)
"Such a lovely place!It was spotless and peaceful"
United States
Marilee G.
Hidden Log Cabin | Hot Tub | Ping Pong | Family |
House | 2 bedrooms

9. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is AED 741
AED 1,372 total
includes taxes & fees
24 Sep - 25 Sep
Farm Country Amish Country Newly Renovated
House | 3 bedrooms

10. Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
The price is AED 791
AED 1,472 total
includes taxes & fees
30 Sep - 1 Oct
Hidden Log Cabin Hot Tub Ping Pong Family
Exterior

11. Hearthstone Hideaway #5 | Shewana Tiny Home Village

Hearthstone Hideaway #5 | Shewana Tiny Home Village
Shipshewana
9.4 out of 10, Exceptional, (6 reviews)
"We enjoyed staying at the tiny house. Was clean and quiet. Had about everything we needed for are two night stay. Will be back"
United States
Joe R.
The price is AED 339
AED 783 total
includes taxes & fees
27 Sep - 28 Sep
Hearthstone Hideaway #5 | Shewana Tiny Home Village
House | 2 bedrooms

12. 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 AED 488
AED 1,009 total
includes taxes & fees
28 Sep - 29 Sep
Lake Front Cottage Kayaks Game Table Fun
Property grounds

13. Relax and Unwind at the Cozy Cabin on Heaton Lake.

Relax and Unwind at the Cozy Cabin on Heaton Lake.
Elkhart
10.0 out of 10, Exceptional, (45 reviews)
"Everything was as advertised. Excellent quiet location. Easy access to gorgeous lake. Clean well stocked home with garage Just like being at home. Short commute to NotreDame."
United States
donald
The price is AED 397
AED 703 total
includes taxes & fees
24 Sep - 25 Sep
Relax and Unwind at the Cozy Cabin on Heaton Lake.
Exterior

14. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (322 reviews)
"Great property. Good location. Would stay again."
United States
BigJohnsCards24
The price is AED 529
AED 765 total
includes taxes & fees
30 Sep - 1 Oct
Millie's Cottage
Lobby

15. Premium King Bed | Daylight Inn Elkhart I-90, IN

Premium King Bed | Daylight Inn Elkhart I-90, IN
Elkhart IN
10.0 out of 10, Exceptional, (221 reviews)
"Relaxing stay overall,perfect rest before continuing our trip!"
United States
Anonymous traveler
Premium King Bed | Daylight Inn Elkhart I-90, IN
Exterior

16. Serene Sanctuary | Tiny Home #1 in Amish Country!

Serene Sanctuary | Tiny Home #1 in Amish Country!
Shipshewana
10.0 out of 10, Exceptional, (6 reviews)
"Loved the tiny house "
United States
Karen M.
The price is AED 339
AED 893 total
includes taxes & fees
24 Sep - 25 Sep
Serene Sanctuary | Tiny Home #1 in Amish Country!
2 bedrooms, WiFi (free), bed sheets

17. Simple Serenity Loft | Tiny Home #6 in Amish Country!

Simple Serenity Loft | Tiny Home #6 in Amish Country!
Shipshewana
9.4 out of 10, Exceptional, (6 reviews)
"This place was amazing! The animals in the back were a bonus. The only thing we could think to make it better was a full length mirror. Would recommend to all our family and friends to stay here!"
United States
Cindy T.
The price is AED 339
AED 901 total
includes taxes & fees
27 Sep - 28 Sep
Simple Serenity Loft | Tiny Home #6 in Amish Country!
Exterior

18. Nature's Nest | Tiny Home #4 in Amish Country!

Nature's Nest | Tiny Home #4 in Amish Country!
Shipshewana
10.0 out of 10, Exceptional, (14 reviews)
"Very clean, quiet and cosy. For being a tiny house we had anything we needed. Location is great.The bed and mattress were very comfortable"
United States
L D.
The price is AED 339
AED 775 total
includes taxes & fees
24 Sep - 25 Sep
Nature's Nest | Tiny Home #4 in Amish Country!
Exterior

19. Natural Nook | Tiny Home #2 in Amish Country!

Natural Nook | Tiny Home #2 in Amish Country!
Shipshewana
9.6 out of 10, Exceptional, (20 reviews)
"If you're looking for a peaceful, beautiful place, this tiny house is it! Tranquil and everything you need for a weekend getaway."
United States
Michelle H.
The price is AED 339
AED 893 total
includes taxes & fees
24 Sep - 25 Sep
Natural Nook | Tiny Home #2 in Amish Country!
Terrace/patio

20. Beautiful Private Setting !!!

Beautiful Private Setting !!!
Bristol
10.0 out of 10, Exceptional, (29 reviews)
"Great setting and well supplied. "
United States
Audrey H.
The price is AED 790
AED 1,514 total
includes taxes & fees
26 Sep - 27 Sep
Beautiful Private Setting !!!
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
"The room was clean but a bit dated. The staff was nice. The location was perfect fit all the Shipshewana and Middlebury activities."
Chris 1-night trip
Posted less than an hour ago
Der Ruhe Blatz Motel

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.

What's the top vacation rental in Middlebury?

Millie's Cottage: This vacation home rental outside of Middlebury is located in the city center and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a private yard and a selection of games.

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.