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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (76 reviews)
"Excellent place to stay, planning on staying again when we come to visit family. "
United States
Cara B.
$176 nightly
The price is $188
Nov 8 - Nov 9
Total with taxes and fees
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, (78 reviews)
"Great location"
United States
Tracy C.
$260 nightly
The price is $261
Nov 8 - Nov 9
Total with taxes and fees
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
A hot tub with a view of a grassy field and a cloudy sky.

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

| Hot Tub | Amish Farm Country | Pergola | Deck |
Middlebury
10.0 out of 10, Exceptional, (104 reviews)
"This was a warm and cozy stay! "
United States
Tim B.
$254 nightly
The price is $254
Nov 23 - Nov 24
Total with taxes and fees
| 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.

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

| Amish Country Getaway | Farm Views | Fire Pit |
Middlebury
10.0 out of 10, Exceptional, (6 reviews)
"Great little farmhouse for the family."
United States
Arlen K.
$250 nightly
The price is $251
Nov 10 - Nov 11
Total with taxes and fees
| Amish Country Getaway | Farm Views | Fire Pit |
A kitchen with a double sink, light-colored cabinets, and a refrigerator.

5. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
$286 nightly
The price is $306
Nov 23 - Nov 24
Total with taxes and fees
Farm Country Amish Country Newly Renovated
A wooden deck with a view of a calm lake, a dock, and a boat.

6. The Wellington Cottage

The Wellington Cottage
3.0 star property
Middlebury
10.0 out of 10, Exceptional, (12 reviews)
"Enjoyed our 2- night stay here."
United States
Phil
$114 nightly
The price is $131
Nov 11 - Nov 12
Total with taxes and fees
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, (35 reviews)
"Loved the house. Clean and comfortable and convenient to shipshewana and goshen."
United States
Dianna D.
$320 nightly
The price is $342
Nov 9 - Nov 10
Total with taxes and fees
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
$269 nightly
The price is $288
Nov 10 - Nov 11
Total with taxes and fees
Amish Country Getaway Farm Views Fire Pit
A cozy seating area with wicker chairs and a teal rug, a 'Welcome to our Lake House' sign, and nautical decorations.

9. 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
$189 nightly
The price is $218
Nov 24 - Nov 25
Total with taxes and fees
Lake Front Cottage Kayaks Game Table Fun
A spacious living room with a brown leather sofa, a wooden coffee table, and a patterned rug.

10. The Lilly Pad Retreat at Frog Pond

The Lilly Pad Retreat at Frog Pond
Jefferson Township
$275 nightly
The price is $277
Nov 8 - Nov 9
Total with taxes and fees
The Lilly Pad Retreat at Frog Pond
A small, single-story building with a dark roof and a welcoming entrance.

11. 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
$211 nightly
The price is $242
Nov 9 - Nov 10
Total with taxes and fees
Natural Nook | Tiny Home #2 in Amish Country!
A covered porch with two chairs and a table, a brick wall, and string lights.

12. 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, (55 reviews)
"We had a great stay!!"
United States
Sally F.
$350 nightly
The price is $375
Nov 8 - Nov 9
Total with taxes and fees
Superb 5-bedroom farmhouse in Goshen with WiFi, AC
A house with a porch, a window with a flower box, and a chair outside.

13. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (336 reviews)
"Great place to stay"
United States
Joshua H.
$156 nightly
The price is $179
Nov 15 - Nov 16
Total with taxes and fees
Millie's Cottage
A spacious kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

14. Arrowhead Riverfront! Beautiful, Peaceful, Private

Arrowhead Riverfront! Beautiful, Peaceful, Private
Bristol
10.0 out of 10, Exceptional, (7 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.
$425 nightly
The price is $454
Nov 9 - Nov 10
Total with taxes and fees
Arrowhead Riverfront! Beautiful, Peaceful, Private
A spacious loft with a stone fireplace, large windows, and a cozy seating area.

15. Riverhaven! Glamorous A-Frame on St Joe River!

Riverhaven! Glamorous A-Frame on St Joe River!
Bristol
9.0 out of 10, Wonderful, (8 reviews)
"Beautiful place to stay! The home was very clean and the location was perfect!"
United States
Emmajo R.
$452 nightly
The price is $484
Nov 9 - Nov 10
Total with taxes and fees
Riverhaven! Glamorous A-Frame on St Joe River!
Exterior

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.
$587 nightly
The price is $645
Nov 8 - Nov 9
Total with taxes and fees
Hilltop Family Retreat
A room with a large window overlooking a lake, a ceiling fan, a wooden dining table with chairs, and a sofa.

17. 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, (50 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
$177 nightly
The price is $189
Nov 9 - Nov 10
Total with taxes and fees
Relax and Unwind at the Cozy Cabin on Heaton Lake.
A cozy room with wicker chairs, a rocking chair, a teal rug, and a sign reading "Welcome to our Lake House."

18. 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.
$182 nightly
The price is $184
Nov 24 - Nov 25
Total with taxes and fees
Lake Front Cottage | Kayaks | Game Table Fun
A wooden deck with a view of a lake, a covered seating area, and a building with a window.

19. Sunset Point: Spacious 4-bedroom house in Elkhart with WiFi, AC, Swim Spa

Sunset Point: Spacious 4-bedroom house in Elkhart with WiFi, AC, Swim Spa
Elkhart
6.8 out of 10, (3 reviews)
"We came here with 8 people, four young kids, we had fun in the hot tub and the sleeping arraignments were great, beds were comfortable enough and the kids loved the swim spa, and the view is super cool, watching birds and wild life in the river. We would recommend this place even in the winter. "
United States
Cara H.
$445 nightly
The price is $476
Nov 9 - Nov 10
Total with taxes and fees
Sunset Point: Spacious 4-bedroom house in Elkhart with WiFi, AC, Swim Spa
A two-story house with a porch, stone pillars, and a red barn in the background.

20. Rock Run Creek House

Rock Run Creek House
Goshen
9.6 out of 10, Exceptional, (5 reviews)
"Close to Shipshe and a beautiful property"
United States
Holly A.
$587 nightly
The price is $645
Nov 8 - Nov 9
Total with taxes and fees
Rock Run Creek House
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

Blue Gate Garden Inn

Blue Gate Garden Inn

10/10 Excellent
"Already decorated for Christmas! We came for a show at the Blue Gate Theater, and stayed at their inn because of the convenience. We’ll stay again though because the hotel was clean and well-curated; the bed and pillows were A+; and the buffet at dinner and at the (free!) was very very good. Everything tasted delicious, and cleanliness protocols were honored very well!"
Bridget 1-night trip
Posted less than an hour ago
Blue Gate Garden Inn

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Middlebury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $59 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.