Photo by Ann Sair

Middlebury Holiday Rentals

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Holiday Rentals in Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

2.0 star property
Middlebury
10.0 out of 10, Exceptional, (40)
"Very nice place a little into the countryside. Will definitely stay again next time I’m in the area."
United States
Brad
The price is NZ$254
includes taxes & fees
20 Nov - 21 Nov
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

Middlebury
10.0 out of 10, Exceptional, (62)
"Overall a good place to stay in the area."
United States
Tyrel S.
The price is NZ$549
includes taxes & fees
23 Nov - 24 Nov
HOT TUB | Beautiful Backyard Oasis|Newly Renovated

The Wellington Cottage

3.0 star property
Middlebury
10.0 out of 10, Exceptional, (5)
"The cottage is adorable and well stocked for travelers!! I wish I could have stayed and enjoyed the beautiful fall lake views! The area and surrounding houses are well kept and seem quite safe! Easy access and convenient parking. I regret forgetting to read the previous ones or leave a note with the others on the fridge! "
United States
Barbara
The Wellington Cottage

The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Middlebury
10.0 out of 10, Exceptional, (25)
"Very relaxing. Wonderful back porch. Very clean"
Canada
Julie A.
The price is NZ$559
includes taxes & fees
17 Nov - 18 Nov
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Middlebury
9.6 out of 10, Exceptional, (25)
"Great location and view. Because of our age we had bedroom to bathroom difficulties. "
United States
Cris F.
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

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

Middlebury
10.0 out of 10, Exceptional, (91)
"Beautiful house, well equipped (including an outdoor hot tub!), clean, comfortable, top-notch. We're definitely hoping to stay there again sometime."
United States
Joel J N.
The price is NZ$440
includes taxes & fees
20 Nov - 21 Nov
| Hot Tub | Amish Farm Country | Pergola | Deck |

Hidden Log Cabin | Hot Tub | Ping Pong | Family |

Goshen
10.0 out of 10, Exceptional, (10)
"What a great place! So secluded and quiet and just what we needed. Loved the hot tub and playing ping pong. It was a blast. Wish we could have stayed another day!"
United States
Mary R.
Hidden Log Cabin | Hot Tub | Ping Pong | Family |

Nautical 5 Bedroom 5 Bathroom Home on Diamond Lake

Cassopolis
9.8 out of 10, Exceptional, (18)
"This was a great stay for our extended family vacation "
United States
Danielle O.
Nautical 5 Bedroom 5 Bathroom Home on Diamond Lake

Relax and unwind at the Cozy Cabin on Heaton Lake.

2.0 star property
Elkhart
10.0 out of 10, Exceptional, (23)
"This property was wonderful! Great use of the space and very clean and beautiful decor! Peaceful lake and having the kayaks was perfect. If we need to be in the area again, will book here for sure! "
United States
Ann S.
The price is NZ$312
includes taxes & fees
17 Nov - 18 Nov
Relax and unwind at the Cozy Cabin on Heaton Lake.

Lake Retreat With Hot Tub

Howe
10.0 out of 10, Exceptional, (24)
"Such a lovely place to stay with so many personal touches. Owners reached out to check in and make sure our trip was really nice! I would love to come back!"
United States
Anonymous traveller
The price is NZ$315
includes taxes & fees
18 Nov - 19 Nov
Lake Retreat With Hot Tub

Live & Love Life on the Lake at Sunset Peak!

Howe
9.8 out of 10, Exceptional, (22)
"Very peaceful property in a quiet neighborhood. Very clean and beautifully decorated. Had a nice lake view from both levels of the house. House had lots of room - bedrooms were big! Nice open concept from kitchen, dining and living room. 3 big tvs but we never turned them on. Would like to come back someday. We visited Shipshewana and drive was about 18 minutes away, so not bad at all."
United States
Tammy D.
The price is NZ$554
includes taxes & fees
17 Nov - 18 Nov
Live & Love Life on the Lake at Sunset Peak!

Live & Love Life on the Lake at Sunset Cottage!

Howe
9.6 out of 10, Exceptional, (57)
"We love staying at Sunset Cottage! Peaceful, private vacation. Great nearby restaurants as well.Host Krista Mayo is wonderful!"
United States
Kim T.
The price is NZ$445
includes taxes & fees
17 Nov - 18 Nov
Live & Love Life on the Lake at Sunset Cottage!

Emma's Place

LaGrange
10.0 out of 10, Exceptional, (56)
"Came to visit family in the area. "
United States
Cara B.
The price is NZ$597
includes taxes & fees
17 Nov - 18 Nov
Emma's Place

Hoops & Hearth, Indoor Pool Near Notre Dame

Mishawaka
9.2 out of 10, Wonderful, (23)
"We were super excited to book this house for our first ever family vacation. Upon arrival we were very disappointed as the pictures online were not a correct representation of the house. The floors were not swept, not mopped and the carpets weren't much better. While this wouldn't normal be a big deal, we didn't want to spend our our first vacation in 3 years cleaning a house upon arrival, especially after having to pay a pretty large cleaning fee. The indoor pool area is very slippery and there...
United States
Arielle C.
Hoops & Hearth, Indoor Pool Near Notre Dame

Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi

Elkhart
10.0 out of 10, Exceptional, (9)
"Well maintained space, with everything you may need if you forgot or ran low! Hosts were responsive to any questions we had. Very relaxing and peaceful, neighborhood environment. "
United States
Lisa
Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi

Newly Remodeled Cabin Steps from Sylvan Lake

Rome City
10.0 out of 10, Exceptional, (47)
"Nice little place for my wife and I prior to a state conference. Good access to lake and kayaks were provided. Good proximity to Amish country. "
United States
Kevin B.
Newly Remodeled Cabin Steps from Sylvan Lake

Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

Shipshewana
9.8 out of 10, Exceptional, (32)
"We had a lovely time in Shipshewana. The rental was very nice, and very comfortable. "
United States
Julie M.
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

Perfect couple's retreat or family getaway less than an hour from Lake Michigan!

Marcellus
9.6 out of 10, Exceptional, (22)
"Debi was great and my son and I enjoyed fishing off of a paddle boat we rented."
United States
Zach B.
Perfect couple's retreat or family getaway less than an hour from Lake Michigan!

Book your Fall Getaway now ! Our Season ends November 22!

Goshen
8.8 out of 10, Excellent, (5)
"This host has a super comfortable and accommodating set up. No detail was left to spare with the outdoor amenities. Comfortable lounging, items for a fire in the provided fire pit, plenty for the kids to enjoy, nicely groomed walking trails, and a comfortable camper with all needed amenities. We had a great week staying here. My family will enjoy these memories for a very long time. Thanks for hosting us! "
United States
Sean B.
Book your Fall Getaway now ! Our Season ends November 22!

Cozy little lake cottage on Buck Lake!

Vandalia
10.0 out of 10, Exceptional, (13)
"Very peaceful and quiet location. Enjoyed nearby park for hiking. Beautiful view of lake from porch. "
United States
sharon k.
The price is NZ$477
includes taxes & fees
17 Nov - 18 Nov
Cozy little lake cottage on Buck Lake!
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

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, 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 NZ$254 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?

HOT TUB | Beautiful Backyard Oasis|Newly Renovated: This highly rated holiday home rental in Middlebury offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind. Some other homes for rent in Middlebury include The Back Porch Haven Stay in Amish Country yet close to Notre Dame and Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame..

How many holiday rentals will I find in Middlebury?

With 15 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 Trout 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.