A log cabin with red shutters and a small porch.

Middlebury Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Middlebury holiday rentals

Outdoor spa tub

1. HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Middlebury
10.0 out of 10, Exceptional, (73 reviews)
"This is a great Property!"
United States
Patrick B.
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Property grounds

2. 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, (68 reviews)
"Excellent place to stay, planning on staying again when we come to visit family. "
United States
Cara B.
The price is HK$1,216
HK$1,485 total
includes taxes & fees
27 Sept - 28 Sept
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Outdoor spa tub

3. | 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 HK$1,009
HK$2,275 total
includes taxes & fees
24 Sept - 25 Sept
| Hot Tub | Amish Farm Country | Pergola | Deck |
Terrace/patio

4. 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 HK$910
HK$1,092 total
includes taxes & fees
11 Oct - 12 Oct
The Wellington Cottage
Room

5. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is HK$1,183
HK$2,504 total
includes taxes & fees
24 Sept - 25 Sept
Farm Country Amish Country Newly Renovated
Living area

6. 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, (32 reviews)
"Loved the house. Clean and comfortable and convenient to shipshewana and goshen."
United States
Dianna D.
The price is HK$1,153
HK$2,585 total
includes taxes & fees
12 Oct - 13 Oct
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Room

7. Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
The price is HK$1,108
HK$2,522 total
includes taxes & fees
16 Sept - 17 Sept
Hidden Log Cabin Hot Tub Ping Pong Family
Exterior

8. 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 HK$725
HK$1,907 total
includes taxes & fees
17 Sept - 18 Sept
Natural Nook | Tiny Home #2 in Amish Country!
Exterior

9. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (320 reviews)
"Great property. Good location. Would stay again."
United States
BigJohnsCards24
The price is HK$1,129
HK$1,641 total
includes taxes & fees
20 Sept - 21 Sept
Millie's Cottage
Property grounds

10. 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, (44 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 HK$882
HK$1,540 total
includes taxes & fees
21 Sept - 22 Sept
Relax and Unwind at the Cozy Cabin on Heaton Lake.
Terrace/patio

11. Beautiful Private Setting !!!

Beautiful Private Setting !!!
Bristol
10.0 out of 10, Exceptional, (29 reviews)
"Great setting and well supplied. "
United States
Audrey H.
Beautiful Private Setting !!!
Room

12. Lake House Shallow Sandy Kayaks Family Fun

Lake House Shallow Sandy Kayaks Family Fun
2.0 star property
Shipshewana
The price is HK$1,391
HK$3,196 total
includes taxes & fees
17 Sept - 18 Sept
Lake House Shallow Sandy Kayaks Family Fun
Lobby

13. 2 Queen Bed | Non-Smoking

2 Queen Bed | Non-Smoking
Elkhart IN
10.0 out of 10, Exceptional, (201 reviews)
"Clean sheets on comfortable beds made sleep easy every night we were there!"
United States
Anonymous traveller
The price is HK$386
HK$500 total
includes taxes & fees
17 Sept - 18 Sept
2 Queen Bed | Non-Smoking
Terrace/patio

14. Superb 5-bedroom farmhouse in Goshen with WiFi, AC

Superb 5-bedroom farmhouse in Goshen with WiFi, AC
Goshen
9.8 out of 10, Exceptional, (49 reviews)
"We had a great stay!!"
United States
Sally F.
The price is HK$1,953
HK$2,375 total
includes taxes & fees
15 Sept - 16 Sept
Superb 5-bedroom farmhouse in Goshen with WiFi, AC
Outdoor dining

15. Live & Love Life on the Lake at Sunset Cottage!

Live & Love Life on the Lake at Sunset Cottage!
Howe
9.6 out of 10, Exceptional, (75 reviews)
"Nice for a short visit."
United States
Bob W.
The price is HK$819
HK$1,952 total
includes taxes & fees
20 Sept - 21 Sept
Live & Love Life on the Lake at Sunset Cottage!
Interior

16. Arrowhead Riverfront! Beautiful, Peaceful, Private

Arrowhead Riverfront! Beautiful, Peaceful, Private
Bristol
10.0 out of 10, Exceptional, (3 reviews)
"This was a lovely location, quiet and relaxing, for a visit with our family from Elkhart. It has plenty of room, a well-stocked kitchen, and was very clean. It’s close to a grocery store and several small towns that we like to visit."
United States
Dawn W.
The price is HK$1,588
HK$3,722 total
includes taxes & fees
15 Sept - 16 Sept
Arrowhead Riverfront! Beautiful, Peaceful, Private
Living area

17. The Gemini

The Gemini
Elkhart
9.2 out of 10, Wonderful, (15 reviews)
"Very clean, had everything we needed and the host was great to communicate with. One of the best places we have ever stayed."
United States
Kelly C.
The price is HK$910
HK$1,067 total
includes taxes & fees
17 Sept - 18 Sept
The Gemini
Living area

18. Queen Bed Non-Smoking

Queen Bed Non-Smoking
Sturgis, MI
10.0 out of 10, Exceptional, (182 reviews)
"Rooms were cozy, just what you need after a long drive. Very happy with our stay overall!"
United States
Anonymous traveller
The price is HK$404
HK$604 total
includes taxes & fees
15 Sept - 16 Sept
Queen Bed Non-Smoking
Exterior detail

19. Emma's Place

Emma's Place
LaGrange
9.8 out of 10, Exceptional, (74 reviews)
"Inside very clean. Nice neighborhood. Would stay again"
United States
Kenny M.
The price is HK$1,137
HK$2,697 total
includes taxes & fees
15 Sept - 16 Sept
Emma's Place
Dining

20. Riverhaven! Glamorous A-Frame on St Joe River!

Riverhaven! Glamorous A-Frame on St Joe River!
Bristol
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful place to stay! The home was very clean and the location was perfect!"
United States
Emmajo R.
Riverhaven! Glamorous A-Frame on St Joe River!
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

Blue Gate Garden Inn

Blue Gate Garden Inn

10/10 Excellent
"This is a very large property but the entire place was immaculate, including our room. Many amenities available and seasonal decorations were amazing."
Mary Ellen 1-night trip
Posted 5 hours ago
Blue Gate Garden Inn

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:

  • 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.

What are some of the best holiday rentals that Middlebury has to offer?

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.: This highly rated holiday home rental in Middlebury is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Trout 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 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.