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

Our top choices for Middlebury vacation rentals

A gravel path leading to a white house with a garage, surrounded by grassy fields and trees.

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 ￥24,316
￥29,711 total
includes taxes & fees
Sep 27 - Sep 28
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
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, (76 reviews)
"This is a great Property!"
United States
Patrick B.
The price is ￥35,792
￥61,723 total
includes taxes & fees
Oct 8 - Oct 9
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
A house with a white picket fence, a front porch with two rocking chairs, and a brick pathway leading to the door.

3. 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.
The price is ￥38,749
￥66,305 total
includes taxes & fees
Sep 27 - Sep 28
Charming 3-bedroom house located on Main Street in Downtown Middlebury
A hot tub with a view of a grassy field and a cloudy sky.

4. | 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.
| Hot Tub | Amish Farm Country | Pergola | Deck |
A waterfront view with an American flag, a boat, and a sunset.

5. 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 ￥18,214
￥21,849 total
includes taxes & fees
Oct 11 - Oct 12
The Wellington Cottage
A kitchen with light green cabinets, a white island with stools, a stainless steel refrigerator, and a 'Coffee' sign on the wall.

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

| Amish Country Getaway | Farm Views | Fire Pit |
Middlebury
10.0 out of 10, Exceptional, (3 reviews)
"Great location! Close to Shipshewana and shopping and restaurants. Extremely clean, roomy, and had everything you need for a great stay."
United States
Tamara B.
The price is ￥17,437
￥39,562 total
includes taxes & fees
Sep 28 - Sep 29
| Amish Country Getaway | Farm Views | Fire Pit |
A kitchen with a double sink, light-colored cabinets, and a refrigerator.

7. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is ￥32,711
￥59,761 total
includes taxes & fees
Sep 24 - Sep 25
Farm Country Amish Country Newly Renovated
A log cabin interior with a dining area, a living room with a sofa and armchair, a coffee bar, and a wooden staircase.

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 |
A spacious living room with a high ceiling, exposed wooden beams, a brick wall, a staircase, and a large television.

9. 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 ￥22,206
￥52,633 total
includes taxes & fees
Sep 22 - Sep 23
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
A log cabin interior with a dining area, a living room, a staircase, and a coffee bar.

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 ￥35,725
￥64,966 total
includes taxes & fees
Sep 30 - Oct 1
Hidden Log Cabin Hot Tub Ping Pong Family
A two-story house with a front porch, a grill, and a door with a wreath.

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.
The price is ￥33,745
￥64,644 total
includes taxes & fees
Sep 26 - Sep 27
Beautiful Private Setting !!!
A kitchen with a coffee maker, a coffee mug rack, and a view of a lake through a window.

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

Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax
Shipshewana
The price is ￥29,735
￥62,954 total
includes taxes & fees
Sep 23 - Sep 24
Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax
A lakeside seating area with Adirondack chairs and a canoe, surrounded by a grassy area and a large tree.

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

Lake House | Shallow Sandy | Kayaks | Family Fun
Middlebury
9.8 out of 10, Exceptional, (10 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 ￥40,932
￥74,567 total
includes taxes & fees
Oct 1 - Oct 2
Lake House | Shallow Sandy | Kayaks | Family Fun
A spacious living room with a wooden dining table, chairs, a television, and a large window with curtains.

14. Lake House Shallow Sandy Kayaks Family Fun

Lake House Shallow Sandy Kayaks Family Fun
2.0 star property
Shipshewana
The price is ￥44,653
￥83,284 total
includes taxes & fees
Oct 1 - Oct 2
Lake House Shallow Sandy Kayaks Family Fun
A covered porch with two chairs and a table, a brick wall, and string lights.

15. 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 ￥39,063
￥47,505 total
includes taxes & fees
Sep 27 - Sep 28
Superb 5-bedroom farmhouse in Goshen with WiFi, AC

16. Hilltop Family Retreat

Hilltop Family Retreat
Goshen
10.0 out of 10, Exceptional, (7 reviews)
"Well maintained and had everything you could need!"
United States
Rosie B.
The price is ￥58,830
￥88,847 total
includes taxes & fees
Oct 18 - Oct 19
Hilltop Family Retreat
A small, single-story house with a dark roof, a front porch with two chairs, and a pathway leading to the entrance.

17. 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 ￥14,496
￥38,139 total
includes taxes & fees
Sep 27 - Sep 28
Natural Nook | Tiny Home #2 in Amish Country!
A long table with candles and greenery, set against a wooden backdrop with vertical strings of lights.

18. Rock Run Creek House

Rock Run Creek House
Goshen
9.6 out of 10, Exceptional, (5 reviews)
"was a fantastic rental. Thank you so much!"
United States
Lavern Y.
The price is ￥72,165
￥106,301 total
includes taxes & fees
Oct 5 - Oct 6
Rock Run Creek House
A house with a porch, a window with a flower box, and a chair outside.

19. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (321 reviews)
"Great property. Good location. Would stay again."
United States
BigJohnsCards24
The price is ￥22,591
￥32,655 total
includes taxes & fees
Sep 30 - Oct 1
Millie's Cottage
A spacious kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

20. 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 ￥29,227
￥71,392 total
includes taxes & fees
Sep 23 - Sep 24
Arrowhead Riverfront! Beautiful, Peaceful, Private
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

Van Buren Hotel

Van Buren Hotel

10/10 Excellent
"Such a cute, quaint property. It is so charming! Staff were all so kind. Breakfast was nice! Had a tiny issue with the elevator, but the staff were very kind about it! Highly recommend this place. Lots of fun shops and eateries close by."
Kimberly 1-night trip
Posted 2 hours ago
Van Buren Hotel

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
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  • 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 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 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.