A log cabin with red shutters and a small porch.

Middlebury Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Middlebury vacation homes

House

Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is CA $250
CA $484 total
includes taxes & fees
Jul 13 - Jul 14
Farm Country Amish Country Newly Renovated
Outdoor spa tub

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

| Hot Tub | Amish Farm Country | Pergola | Deck |
Middlebury
10.0 out of 10, Exceptional, (100 reviews)
"This was a warm and cozy stay! "
United States
Tim B.
The price is CA $185
CA $418 total
includes taxes & fees
Jul 13 - Jul 14
| Hot Tub | Amish Farm Country | Pergola | Deck |
Outdoor spa tub

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Middlebury
10.0 out of 10, Exceptional, (70 reviews)
"Nice, quiet place for a ladies weekend. Would recommend and stay here again."
United States
Stephanie K.
The price is CA $271
CA $498 total
includes taxes & fees
Jul 9 - Jul 10
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Smart TV, books

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, (31 reviews)
"Everything was as advertised and the host was great. Highly recommend!"
United States
Bart W.
The price is CA $244
CA $534 total
includes taxes & fees
Jul 19 - Jul 20
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Smart TV, DVD player

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

Hidden Log Cabin | Hot Tub | Ping Pong | Family |
Goshen
10.0 out of 10, Exceptional, (11 reviews)
"Such a lovely place!It was spotless and peaceful"
United States
Marilee G.
The price is CA $274
CA $535 total
includes taxes & fees
Jul 9 - Jul 10
Hidden Log Cabin | Hot Tub | Ping Pong | Family |
Fridge, microwave, oven, stovetop

| Amish Country Getaway | Farm Views | Fire Pit |

| Amish Country Getaway | Farm Views | Fire Pit |
Middlebury
10.0 out of 10, Exceptional, (2 reviews)
"Great little farmhouse for the family."
United States
Arlen K.
| Amish Country Getaway | Farm Views | Fire Pit |
House

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
House

Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
The price is CA $452
CA $717 total
includes taxes & fees
Jul 16 - Jul 17
Hidden Log Cabin Hot Tub Ping Pong Family
Exterior

Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (302 reviews)
"Very nice place .. very clean! Would stay here again! "
United States
Monica N.
The price is CA $204
CA $294 total
includes taxes & fees
Jul 9 - Jul 10
Millie's Cottage
House

Relaxing Riverside 10 Minutes to Shipshewana

Relaxing Riverside 10 Minutes to Shipshewana
2.0 star property
Howe
Relaxing Riverside 10 Minutes to Shipshewana
Exterior detail

Amish Alley Guesthouse,no cleaning fee,near TLA

Amish Alley Guesthouse,no cleaning fee,near TLA
Topeka
9.4 out of 10, Exceptional, (3 reviews)
"Everything was great. Nice cozy home. The only downside was the shower was too small. If it had at least another half bathroom would be perfect."
United States
Mario
The price is CA $284
CA $372 total
includes taxes & fees
Jul 12 - Jul 13
Amish Alley Guesthouse,no cleaning fee,near TLA
Fridge, microwave, oven, stovetop

Kayaks | Relax by River | 10 Min to Shipshewana |

Kayaks | Relax by River | 10 Min to Shipshewana |
Howe
10.0 out of 10, Exceptional, (26 reviews)
"We had a great stay. It was really clean and comfortable, and I loved being able to kayak. It was a perfect place for a relaxing few days."
United States
Christine C.
Kayaks | Relax by River | 10 Min to Shipshewana |
Property grounds

Lake House | Shallow Sandy | Kayaks | Family Fun

Lake House | Shallow Sandy | Kayaks | Family Fun
Middlebury
10.0 out of 10, Exceptional, (7 reviews)
"Incredible stay. They’ve thought of everything you would need for an enjoyable and relaxing vacation. A dream cottage. "
United States
Larry
Lake House | Shallow Sandy | Kayaks | Family Fun
Outdoor dining

Cozy Lake House On The Channel With Access To 5 Lakes!

Cozy Lake House On The Channel With Access To 5 Lakes!
Wolcottville
9.4 out of 10, Exceptional, (48 reviews)
"Nice Property, affordable, pice and Nice Location. "
United States
Dimple N.
The price is CA $217
CA $436 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Lake House On The Channel With Access To 5 Lakes!
Exterior

Hilltop Family Retreat

Hilltop Family Retreat
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Great house for large group! 5 minutes from downtown Goshen was a plus. Very accommodating! Has all the bells and whistle’s. "
United States
Paul P.
The price is CA $653
CA $962 total
includes taxes & fees
Jul 13 - Jul 14
Hilltop Family Retreat
Dining

Rock Run Creek House

Rock Run Creek House
Goshen
10.0 out of 10, Exceptional, (3 reviews)
"was a fantastic rental. Thank you so much!"
United States
Lavern Y.
The price is CA $653
CA $962 total
includes taxes & fees
Jul 12 - Jul 13
Rock Run Creek House
Fridge, microwave, oven, stovetop

Lakeshore Cottage

Lakeshore Cottage
Elkhart
10.0 out of 10, Exceptional, (21 reviews)
"We had a great trip here to cheer on ND!"
United States
Megan B.
The price is CA $984
CA $1,412 total
includes taxes & fees
Aug 6 - Aug 7
Lakeshore Cottage
Exterior

Lake Haven | Family Getaway with a Pier

Lake Haven | Family Getaway with a Pier
North Webster
The price is CA $305
CA $598 total
includes taxes & fees
Jul 13 - Jul 14
Lake Haven | Family Getaway with a Pier
Property grounds

Live & Love Life on the Lake at Sunset Peak!

Live & Love Life on the Lake at Sunset Peak!
Howe
9.8 out of 10, Exceptional, (39 reviews)
"Beautiful home, Great location and our host was wonderful."
United States
Emily L.
The price is CA $324
CA $630 total
includes taxes & fees
Jul 22 - Jul 23
Live & Love Life on the Lake at Sunset Peak!
House

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 CA $330
CA $547 total
includes taxes & fees
Jul 20 - Jul 21
Lake Front Cottage Kayaks Game Table Fun
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlebury Hotel Reviews

Blue Gate Garden Inn

Blue Gate Garden Inn

10/10 Excellent
"The Blue Gate Garden Inn was the perfect place to stay and enjoy the area. The hotel was exceptionally clean, the customer service was outstanding, and the amenities were the perfect combination to make our stay memorable. My only complaints were that the bed we stayed in was not very comfortable and the AC in the room occasionally made a loud rumbling sound. The bed sunk in the middle causing my arthritis to swell up quite a bit. The AC in our room had some issues also. It made our room comfortable and cool, but occasionally it would make a loud noise which woke me up a few times throughout the night. I informed the front desk upon checking out, and the desk staffer said he would have someone check it out. Other than these two pretty major concerns, I would definitely give this hotel another try if we come to the area again. I would definitely request that we be placed in one of the remodeled or updated rooms instead."
Joseph 1-night trip
Posted 1 hour ago
Blue Gate Garden Inn

Find out more about Middlebury

Middlebury Vacation Homes information

Number of reviews
367
Accommodation
261 Vacation Homes
Lowest Price
CA $294
Highest Price
CA $1,412

Explore a world of travel with Expedia