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.
$255 nightly
The price is $257
Oct 12 - Oct 13
Total with taxes and fees
| 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.
$295 nightly
The price is $298
Nov 1 - Nov 2
Total with taxes and fees
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.
$240 nightly
The price is $242
Oct 12 - Oct 13
Total with taxes and fees
| 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
$285 nightly
The price is $305
Oct 12 - Oct 13
Total with taxes and fees
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.
$177 nightly
The price is $189
Oct 18 - Oct 19
Total with taxes and fees
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
$114 nightly
The price is $131
Nov 1 - Nov 2
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, (34 reviews)
"Loved the house. Clean and comfortable and convenient to shipshewana and goshen."
United States
Dianna D.
$320 nightly
The price is $342
Oct 26 - Oct 27
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 $287
Oct 12 - Oct 13
Total with taxes and fees
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.
$199 nightly
The price is $202
Oct 12 - Oct 13
Total with taxes and fees
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, (7 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.
$184 nightly
The price is $212
Oct 14 - Oct 15
Total with taxes and fees
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
$216 nightly
The price is $248
Oct 12 - Oct 13
Total with taxes and fees
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
$213 nightly
The price is $245
Oct 12 - Oct 13
Total with taxes and fees
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.
$213 nightly
The price is $245
Oct 12 - Oct 13
Total with taxes and fees
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.
$213 nightly
The price is $245
Oct 13 - Oct 14
Total with taxes and fees
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.
$294 nightly
The price is $299
Oct 14 - Oct 15
Total with taxes and fees
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.
$184 nightly
The price is $212
Oct 14 - Oct 15
Total with taxes and fees
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
$306 nightly
The price is $310
Oct 13 - Oct 14
Total with taxes and fees
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.
$184 nightly
The price is $212
Oct 12 - Oct 13
Total with taxes and fees
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.
$213 nightly
The price is $245
Oct 19 - Oct 20
Total with taxes and fees
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.
$182 nightly
The price is $209
Oct 20 - Oct 21
Total with taxes and fees
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

Farmstead Inn & Conference Center

Farmstead Inn & Conference Center

10/10 Excellent
"Nice big clean rooms and bathroom. Everything was advertised. Enjoyed our stay and would stay there again. Good price for location."
CONNIE 1-night trip
Posted less than an hour 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, 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 $61 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.