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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 CA $149
CA $366 total
includes taxes & fees
Oct 19 - Oct 20
| Hot Tub | Amish Farm Country | Pergola | Deck |
A kitchen with light green cabinets, a white island with stools, a stainless steel refrigerator, and a 'Coffee' sign on the wall.

2. | 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 CA $143
CA $343 total
includes taxes & fees
Oct 19 - Oct 20
| Amish Country Getaway | Farm Views | Fire Pit |
A hot tub on a wooden deck with a chair and a blanket.

3. 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 CA $212
CA $405 total
includes taxes & fees
Nov 1 - Nov 2
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
A gravel path leading to a white house with a garage, surrounded by grassy fields and trees.

4. 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 CA $221
CA $272 total
includes taxes & fees
Oct 29 - Oct 30
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
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, (10 reviews)
"Easy 10/10 recommendation Perfect place for peace"
United States
Bonala
The price is CA $140
CA $169 total
includes taxes & fees
Nov 1 - Nov 2
The Wellington Cottage
A kitchen with a double sink, light-colored cabinets, and a refrigerator.

6. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is CA $171
CA $389 total
includes taxes & fees
Oct 19 - Oct 20
Farm Country Amish Country Newly Renovated
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 CA $199
CA $489 total
includes taxes & fees
Oct 14 - Oct 15
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 CA $174
CA $384 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $135
CA $287 total
includes taxes & fees
Oct 14 - Oct 15
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 CA $132
CA $301 total
includes taxes & fees
Oct 14 - Oct 15
Hearthstone Hideaway #5 | Shewana Tiny Home Village
A spacious living room with a wooden dining table, chairs, a television, and a large window with curtains.

11. Lake House Shallow Sandy Kayaks Family Fun

Lake House Shallow Sandy Kayaks Family Fun
2.0 star property
Shipshewana
The price is CA $175
CA $492 total
includes taxes & fees
Oct 19 - Oct 20
Lake House Shallow Sandy Kayaks Family Fun
A house with a porch, a window with a flower box, and a chair outside.

12. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (328 reviews)
"Great place to stay"
United States
Joshua H.
The price is CA $206
CA $299 total
includes taxes & fees
Oct 20 - Oct 21
Millie's Cottage
A spacious dining area with a large table and chairs, a television, and a kitchen area with a coffee station.

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

Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax
Shipshewana
Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax
A hotel lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.

14. 2 Queen Bed | Non-Smoking

2 Queen Bed | Non-Smoking
Elkhart IN
10.0 out of 10, Exceptional, (203 reviews)
"Clean sheets on comfortable beds made sleep easy every night we were there!"
United States
Anonymous traveller
The price is CA $66
CA $86 total
includes taxes & fees
Oct 14 - Oct 15
2 Queen Bed | Non-Smoking
A wooden deck with a hammock and a kayak, overlooking a lake with boats and a dock.

15. 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, (47 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 CA $174
CA $297 total
includes taxes & fees
Oct 16 - Oct 17
Relax and Unwind at the Cozy Cabin on Heaton Lake.
A compact living space with a kitchenette, a sofa, and a television mounted on the wall.

16. Queen Bed Non-Smoking

Queen Bed Non-Smoking
Sturgis, MI
10.0 out of 10, Exceptional, (184 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 CA $71
CA $106 total
includes taxes & fees
Oct 14 - Oct 15
Queen Bed Non-Smoking
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
9.8 out of 10, Exceptional, (22 reviews)
"It was quite and peaceful… beautiful setting… loved the tiny house"
United States
Carla
The price is CA $132
CA $352 total
includes taxes & fees
Oct 22 - Oct 23
Natural Nook | Tiny Home #2 in Amish Country!
A covered porch with two chairs and a table, a brick wall, and string lights.

18. 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, (54 reviews)
"We had a great stay!!"
United States
Sally F.
The price is CA $355
CA $566 total
includes taxes & fees
Oct 29 - Oct 30
Superb 5-bedroom farmhouse in Goshen with WiFi, AC
A modern kitchen with a marble countertop, a built-in oven, and a ceiling fan.

19. 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 CA $132
CA $301 total
includes taxes & fees
Oct 14 - Oct 15
Whispering Cottage #3 | Shewana Tiny Home Village
A two-story building with a wooden facade and a metal roof, featuring a porch with chairs and a small garden area.

20. Serene Sanctuary | Tiny Home #1 in Amish Country!

Serene Sanctuary | Tiny Home #1 in Amish Country!
Shipshewana
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful time!"
United States
Julie G.
Serene Sanctuary | Tiny Home #1 in Amish Country!
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

Farmstead Inn & Conference Center

Farmstead Inn & Conference Center

10/10 Excellent
"Very welcoming and at home feeling throughout the hotel. Couches and seating area located in comfortable “at home” areas. I noticed in the breakfast room all of the oak kitchen tables were taken, leaving the “banquet room “ empty. Very nice to have that at home feeling throughout during a stay away."
Koren 1-night trip
Posted 7 hours ago
Farmstead Inn & Conference Center

Find out more about Middlebury

Everything you need to know about Middlebury vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlebury vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlebury vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlebury. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury vacation rentals we have selected for you start as low as CA $86 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlebury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlebury vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlebury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.