Photo by Ann Sair

Holiday Rentals in Middlebury

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Check prices for these dates

Our top choices for Middlebury holiday rentals

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, (77 reviews)
"This host was very easy to communicate with and allowed us an early check in. Great accommodations…we’d go back for sure!"
United States
Dorothy P.
The price is €179
includes taxes & fees
22 Nov - 23 Nov
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

2. | 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.
The price is €240
includes taxes & fees
23 Nov - 24 Nov
| Hot Tub | Amish Farm Country | Pergola | Deck |

3. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is €278
includes taxes & fees
23 Nov - 24 Nov
Farm Country Amish Country Newly Renovated

4. The Wellington Cottage

The Wellington Cottage
3.0 star property
Middlebury
10.0 out of 10, Exceptional, (13 reviews)
"Enjoyed our 2- night stay here."
United States
Phil
The price is €100
includes taxes & fees
16 Nov - 17 Nov
The Wellington Cottage

5. 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, (36 reviews)
"Loved the house. Clean and comfortable and convenient to shipshewana and goshen."
United States
Dianna D.
The price is €304
includes taxes & fees
15 Nov - 16 Nov
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

6. Hearthstone Hideaway #5 | Shewana Tiny Home Village

Hearthstone Hideaway #5 | Shewana Tiny Home Village
Shipshewana
9.6 out of 10, Exceptional, (13 reviews)
"Very nice stay! Our only negative was that there were more vehicles than parking spaces."
United States
Rita S.
The price is €201
includes taxes & fees
16 Nov - 17 Nov
Hearthstone Hideaway #5 | Shewana Tiny Home Village

7. 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 €198
includes taxes & fees
24 Nov - 25 Nov
Lake Front Cottage Kayaks Game Table Fun

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

Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax
Shipshewana
8.0 out of 10, Very good, (1 review)
"It was a nice clean house just like we expected. It was great"
United States
Ryan K.
Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax

9. Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (339 reviews)
"Great place to stay"
United States
Joshua H.
The price is €173
includes taxes & fees
15 Nov - 16 Nov
Millie's Cottage

10. 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
The price is €188
includes taxes & fees
15 Nov - 16 Nov
Relax and Unwind at the Cozy Cabin on Heaton Lake.

11. 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, (56 reviews)
"We had a great stay!!"
United States
Sally F.
The price is €340
includes taxes & fees
15 Nov - 16 Nov
Superb 5-bedroom farmhouse in Goshen with WiFi, AC

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

Natural Nook | Tiny Home #2 in Amish Country!
Shipshewana
9.8 out of 10, Exceptional, (23 reviews)
"It was quite and peaceful… beautiful setting… loved the tiny house"
United States
Carla
The price is €229
includes taxes & fees
16 Nov - 17 Nov
Natural Nook | Tiny Home #2 in Amish Country!

13. Whispering Cottage #3 | Shewana Tiny Home Village

Whispering Cottage #3 | Shewana Tiny Home Village
Shipshewana
9.4 out of 10, Exceptional, (16 reviews)
"Beautiful and peaceful place."
United States
Jackie S.
The price is €201
includes taxes & fees
16 Nov - 17 Nov
Whispering Cottage #3 | Shewana Tiny Home Village

14. Arrowhead Riverfront! Beautiful, Peaceful, Private

Arrowhead Riverfront! Beautiful, Peaceful, Private
Bristol
10.0 out of 10, Exceptional, (9 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 €395
includes taxes & fees
16 Nov - 17 Nov
Arrowhead Riverfront! Beautiful, Peaceful, Private

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

Little Luxe Retreat #7 | Tiny Home + Fire Table
Shipshewana
10.0 out of 10, Exceptional, (18 reviews)
"Very cozy and well kept up!"
United States
Randy R.
The price is €217
includes taxes & fees
23 Nov - 24 Nov
Little Luxe Retreat #7 | Tiny Home + Fire Table

16. 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.
The price is €230
includes taxes & fees
18 Nov - 19 Nov
Serene Sanctuary | Tiny Home #1 in Amish Country!

17. Designer Apartment-Walkable Downtown Goshen

Designer Apartment-Walkable Downtown Goshen
Goshen
10.0 out of 10, Exceptional, (1 review)
"First, the property is DARLING!!! It was exactly as pictured. We came in for a wedding and it was a block away from the venue. PERFECT. The price was good. Communication from the host was TOP NOTCH. The bed was comfortable. There is a Keurig coffee machine. There is a steamer for your clothing. ***It should be noted that Goshen has a steady stream of trains going through 24/27. If noise bothers you bring a white noise machine or ear plugs. The downtown location (which is very convenient) is also...
United States
Kelly A.
The price is €168
includes taxes & fees
16 Nov - 17 Nov
Designer Apartment-Walkable Downtown Goshen

18. The Gemini

The Gemini
Elkhart
9.4 out of 10, Exceptional, (18 reviews)
"Nice place"
United States
Karla
The price is €127
includes taxes & fees
15 Nov - 16 Nov
The Gemini

19. 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.
The price is €422
includes taxes & fees
16 Nov - 17 Nov
Riverhaven! Glamorous A-Frame on St Joe River!

20. 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, (10 reviews)
"The place was beautiful and very clean and close to town.It was very peaceful and quiet."
United States
audrey o.
The price is €230
includes taxes & fees
16 Nov - 17 Nov
Simple Serenity Loft | Tiny Home #6 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.

Find holiday rentals that suit your style

Find out more about Middlebury

Everything you need to know about Middlebury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlebury holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury holiday rentals we have selected for you start as low as €56 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 holiday 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 holiday.

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 holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Deutsch Kase Haus, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Middlebury has a good selection of restaurants. Make sure you have time to check out the shopping and gardens during your trip.

What are some of the best holiday rentals that Middlebury has to offer?

Millie's Cottage: This holiday home rental outside of Middlebury is located in the city centre, 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 garden and a selection of games.

How many holiday rentals will I find in Middlebury?

With 17 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Middlebury?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlebury. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a small group gathering.