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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Middlebury vacation rentals

A hot tub with a view of a grassy field and a cloudy sky.

1. | 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 ￥16,485
￥40,733 total
includes taxes & fees
Oct 12 - Oct 13
| Hot Tub | Amish Farm Country | Pergola | Deck |
A hot tub on a wooden deck with a chair and a blanket.

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 ￥25,005
￥47,103 total
includes taxes & fees
Nov 1 - Nov 2
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
A kitchen with light green cabinets, a white island with stools, a stainless steel refrigerator, and a 'Coffee' sign on the wall.

3. | Amish Country Getaway | Farm Views | Fire Pit |

| Amish Country Getaway | Farm Views | Fire Pit |
Middlebury
10.0 out of 10, Exceptional, (5 reviews)
"Great little farmhouse for the family."
United States
Arlen K.
The price is ￥15,929
￥38,255 total
includes taxes & fees
Oct 12 - Oct 13
| Amish Country Getaway | Farm Views | Fire Pit |
A kitchen with a double sink, light-colored cabinets, and a refrigerator.

4. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is ￥20,009
￥45,395 total
includes taxes & fees
Oct 12 - Oct 13
Farm Country Amish Country Newly Renovated
A gravel path leading to a white house with a garage, surrounded by grassy fields and trees.

5. 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, (72 reviews)
"Excellent place to stay, planning on staying again when we come to visit family. "
United States
Cara B.
The price is ￥24,538
￥29,982 total
includes taxes & fees
Oct 18 - Oct 19
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
A waterfront view with an American flag, a boat, and a sunset.

6. 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 ￥15,530
￥18,771 total
includes taxes & fees
Nov 1 - Nov 2
The Wellington Cottage
A spacious living room with a high ceiling, exposed wooden beams, a brick wall, a staircase, and a large television.

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 ￥22,163
￥54,205 total
includes taxes & fees
Oct 26 - Oct 27
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
A kitchen with light green cabinets, a white island with stools, a stainless steel refrigerator, and a 'Coffee' sign on the wall.

8. Amish Country Getaway Farm Views Fire Pit

Amish Country Getaway Farm Views Fire Pit
2.0 star property
Middlebury
The price is ￥19,336
￥42,677 total
includes taxes & fees
Oct 12 - Oct 13
Amish Country Getaway Farm Views Fire Pit
A cozy room with wicker chairs, a rocking chair, a teal rug, and a sign reading "Welcome to our Lake House."

9. Lake Front Cottage | Kayaks | Game Table Fun

Lake Front Cottage | Kayaks | Game Table Fun
Shipshewana
9.4 out of 10, Exceptional, (11 reviews)
"Lake Front Cottage was perfect for our weekend stay in LaGrange County. The host was responsive in communication and provided everything we needed for a pleasant stay."
United States
Andrea S.
The price is ￥15,003
￥32,037 total
includes taxes & fees
Oct 12 - Oct 13
Lake Front Cottage | Kayaks | Game Table Fun
A modern building with a sloped roof, a wooden porch, and a small outdoor seating area.

10. Hearthstone Hideaway #5 | Shewana Tiny Home Village

Hearthstone Hideaway #5 | Shewana Tiny Home Village
Shipshewana
9.6 out of 10, Exceptional, (8 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 ￥14,628
￥33,753 total
includes taxes & fees
Oct 15 - Oct 16
Hearthstone Hideaway #5 | Shewana Tiny Home Village
A cozy seating area with wicker chairs and a teal rug, a 'Welcome to our Lake House' sign, and nautical decorations.

11. 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 ￥21,548
￥41,966 total
includes taxes & fees
Oct 21 - Oct 22
Lake Front Cottage Kayaks Game Table Fun
A small, single-story house with a dark roof, a front porch with two chairs, and a pathway leading to the entrance.

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

Natural Nook | Tiny Home #2 in Amish Country!
Shipshewana
9.8 out of 10, Exceptional, (22 reviews)
"It was quite and peaceful… beautiful setting… loved the tiny house"
United States
Carla
The price is ￥14,628
￥38,851 total
includes taxes & fees
Oct 12 - Oct 13
Natural Nook | Tiny Home #2 in Amish Country!
The bedroom has a queen sized bed, electric fireplace, and TV for cozy, restful evenings

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

Simple Serenity Loft | Tiny Home #6 in Amish Country!
Shipshewana
9.6 out of 10, Exceptional, (8 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.
Simple Serenity Loft | Tiny Home #6 in Amish Country!
A two-story building with a wooden facade and a metal roof, featuring a porch with chairs and a small garden area.

14. 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)
"Wonderful time!"
United States
Julie G.
Serene Sanctuary | Tiny Home #1 in Amish Country!
A lakeside seating area with Adirondack chairs and a canoe, surrounded by a grassy area and a large tree.

15. Lake House | Shallow Sandy | Kayaks | Family Fun

Lake House | Shallow Sandy | Kayaks | Family Fun
Middlebury
9.8 out of 10, Exceptional, (13 reviews)
"Great house for a friends getaway. The house is fully equipped to enjoy meals, relax and enjoy the lake. Loved the coffee set up and small extras for guest to enjoy."
United States
Angela D.
The price is ￥17,226
￥47,344 total
includes taxes & fees
Oct 14 - Oct 15
Lake House | Shallow Sandy | Kayaks | Family Fun
A modern kitchen with a marble countertop, a built-in oven, and a ceiling fan.

16. Whispering Cottage #3 | Shewana Tiny Home Village

Whispering Cottage #3 | Shewana Tiny Home Village
Shipshewana
9.0 out of 10, Wonderful, (9 reviews)
"Very awesome place. A bit overpriced but still a good deal and experience."
United States
Edward D.
The price is ￥14,628
￥33,571 total
includes taxes & fees
Oct 14 - Oct 15
Whispering Cottage #3 | Shewana Tiny Home Village
A spacious dining area with a large table and chairs, a television, and a kitchen area with a coffee station.

17. Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax

Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax
Shipshewana
The price is ￥21,931
￥49,556 total
includes taxes & fees
Oct 13 - Oct 14
Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax
A small wooden cabin with a pitched roof, a front door, and two chairs outside.

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 ￥14,628
￥33,571 total
includes taxes & fees
Oct 12 - Oct 13
Nature's Nest | Tiny Home #4 in Amish Country!
A modern two-story house with a dark exterior, a wooden front porch, and a fenced yard.

19. Little Luxe Retreat #7 | Tiny Home + Fire Table

Little Luxe Retreat #7 | Tiny Home + Fire Table
Shipshewana
10.0 out of 10, Exceptional, (16 reviews)
"Very enjoyable stay."
United States
June P.
The price is ￥14,628
￥38,851 total
includes taxes & fees
Oct 19 - Oct 20
Little Luxe Retreat #7 | Tiny Home + Fire Table
A house with a porch, a window with a flower box, and a chair outside.

20. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (327 reviews)
"Great place to stay"
United States
Joshua H.
The price is ￥22,797
￥33,135 total
includes taxes & fees
Oct 20 - Oct 21
Millie's Cottage
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

Sleep Inn Elkhart North

Sleep Inn Elkhart North

8/10 Good
"Great place to stay, my husband was traveling to bring our camper for some needed attention and the hotel was very close to the drop off. He even found a cool place to eat that was walking distance."
Raymond 2-night trip
Posted 1 hour 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?

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 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 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.