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
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Middlebury vacation rentals

Terrace/patio

The Wellington Cottage

The Wellington Cottage
3.0 star property
Middlebury
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful views "
United States
Darwin
The Wellington Cottage
Outdoor spa tub

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

| Hot Tub | Amish Farm Country | Pergola | Deck |
Middlebury
10.0 out of 10, Exceptional, (95 reviews)
"Beautiful house, well equipped (including an outdoor hot tub!), clean, comfortable, top-notch. We're definitely hoping to stay there again sometime."
United States
Joel J N.
The price is ￥12,741
￥34,248 total
includes taxes & fees
Mar 4 - Mar 5
| Hot Tub | Amish Farm Country | Pergola | Deck |
Property grounds

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, (43 reviews)
"Very nice place a little into the countryside. Will definitely stay again next time I’m in the area."
United States
Brad
The price is ￥17,946
￥22,542 total
includes taxes & fees
Mar 4 - Mar 5
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Outdoor spa tub

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Middlebury
10.0 out of 10, Exceptional, (62 reviews)
"The host was very welcoming and made sure everything was to our satisfaction. The house was clean and nice and in a quiet neighborhood. We had a very enjoyable stay."
United States
Judith T.
The price is ￥13,998
￥32,942 total
includes taxes & fees
Mar 4 - Mar 5
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, (27 reviews)
"We had a nice stay with our grandchildren. The house was a very nice space and clean. Our host was friendly and helpful. We loved watching the changing leaves in the yard."
United States
Monica G.
The price is ￥21,535
￥50,927 total
includes taxes & fees
Mar 22 - Mar 23
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Exterior

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

Charming 3-bedroom house located on Main Street in Downtown Middlebury
Middlebury
9.4 out of 10, Exceptional, (13 reviews)
"This was such a cute place, and the beds were so comfortable! My family and I loved staying here!"
United States
Tiffany E.
Charming 3-bedroom house located on Main Street in Downtown Middlebury
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, (10 reviews)
"Such a lovely place!It was spotless and peaceful"
United States
Marilee G.
The price is ￥13,384
￥36,350 total
includes taxes & fees
Mar 5 - Mar 6
Hidden Log Cabin | Hot Tub | Ping Pong | Family |
House | 2 bedrooms

Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is ￥14,929
￥37,262 total
includes taxes & fees
Mar 4 - Mar 5
Farm Country Amish Country Newly Renovated
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, (22 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.
The price is ￥12,203
￥28,276 total
includes taxes & fees
Mar 4 - Mar 5
Kayaks | Relax by River | 10 Min to Shipshewana |
Outdoor dining

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, (57 reviews)
"We had a great time staying here! The view of the lake was gorgeous and it was a very relaxing place to stay. "
United States
Katie H.
The price is ￥13,202
￥34,743 total
includes taxes & fees
Mar 5 - Mar 6
Live & Love Life on the Lake at Sunset Cottage!
Property grounds

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, (25 reviews)
"This was a convenient option over hotel while we were in town. "
United States
Nancy K.
The price is ￥15,449
￥28,219 total
includes taxes & fees
Mar 12 - Mar 13
Relax and unwind at the Cozy Cabin on Heaton Lake.
Exterior

Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (281 reviews)
"Clean, comfortable, great area. Easy to work with owner, always enjoy staying at Millie’s cottage."
United States
Terry K.
The price is ￥21,067
￥31,585 total
includes taxes & fees
Mar 5 - Mar 6
Millie's Cottage
Outdoor spa tub

Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
Goshen
10.0 out of 10, Exceptional, (123 reviews)
"So cute and lots of things to do! We had a wonderful stay!"
United States
Stephanie W.
The price is ￥21,067
￥53,766 total
includes taxes & fees
Mar 5 - Mar 6
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
Exterior detail

Emma's Place

Emma's Place
LaGrange
9.8 out of 10, Exceptional, (59 reviews)
"Very clean, and comfy. We stayed with two other couples and enjoyed our time in this area. "
United States
Michael W.
The price is ￥22,627
￥53,658 total
includes taxes & fees
Mar 4 - Mar 5
Emma's Place
Property grounds

Lake Retreat With Hot Tub

Lake Retreat With Hot Tub
Howe
9.8 out of 10, Exceptional, (31 reviews)
"Thank you so much for your wonderful hospitality! My wife and I had a great stay at the Cozy Nest. It was comfortable and had everything we needed for a relaxing getaway. We would defiantly love to stay again."
United States
Steve R.
The price is ￥21,135
￥27,895 total
includes taxes & fees
Mar 16 - Mar 17
Lake Retreat With Hot Tub
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
9.6 out of 10, Exceptional, (42 reviews)
"Nice Property, affordable, pice and Nice Location. "
United States
Dimple N.
The price is ￥23,876
￥43,250 total
includes taxes & fees
Mar 4 - Mar 5
Cozy Lake House On The Channel With Access To 5 Lakes!
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, (29 reviews)
"The home was very comfortable and had a beautiful setting. The host was kind and responsive."
United States
Alisa Q.
The price is ￥18,679
￥46,606 total
includes taxes & fees
Mar 4 - Mar 5
Live & Love Life on the Lake at Sunset Peak!
Outdoor spa tub

Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife

Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife
Vandalia
10.0 out of 10, Exceptional, (74 reviews)
"Very nice, and very clean, we enjoyed our stay "
United States
Steve
The price is ￥24,062
￥39,345 total
includes taxes & fees
Mar 4 - Mar 5
Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife
Interior

Woodside Retreat in the Heart of Amish Country

Woodside Retreat in the Heart of Amish Country
Nappanee
10.0 out of 10, Exceptional, (12 reviews)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
United States
VICKI
The price is ￥17,946
￥31,391 total
includes taxes & fees
Mar 4 - Mar 5
Woodside Retreat in the Heart of Amish Country
Interior

Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!

Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
Marcellus
9.0 out of 10, Wonderful, (14 reviews)
"We were looking for a place off the beaten path with plenty of privacy and this locstion provided both. The hosts were fantastic and we had a great time. "
United States
Trevor W.
The price is ￥13,264
￥18,741 total
includes taxes & fees
Mar 4 - Mar 5
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
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

Sleep Inn Elkhart North

Sleep Inn Elkhart North

10/10 Excellent
"Safe was really"
Jazmine 1-night trip
Posted 5 hours ago
Sleep Inn Elkhart North

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 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?

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.: Visitors like this Middlebury vacation home rental. It is located on a lake and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Middlebury?

With 12 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.