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Middlebury Holiday Rentals

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Holiday Rentals in Middlebury

Charming 3-bedroom house located on Main Street in Downtown Middlebury

10.0 out of 10, Exceptional, (3)
"We enjoyed and appreciated our stay at The Cozy Cottage. Griffon was very nice and allowed us an early check in and welcomed us to stay as long as we wanted on the day of check out. Would definitely recommend and stay again! "
The price is AU$458
includes taxes & fees
1 Sept - 2 Sept
Charming 3-bedroom house located on Main Street in Downtown Middlebury

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

2.0 star property
10.0 out of 10, Exceptional, (25)
"Would definitely come back!"
The price is AU$224
includes taxes & fees
14 Sept - 15 Sept
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (58)
"Very clean, nicely appointed. Ping pong table and hot tub were a real bonus! "
The price is AU$357
includes taxes & fees
14 Sept - 15 Sept
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

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

10.0 out of 10, Exceptional, (22)
"House was nice & clean, enjoyed our stay!"
The price is AU$495
includes taxes & fees
2 Sept - 3 Sept
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.

9.8 out of 10, Exceptional, (19)
"This property is in a nice location, very pretty. The house was very clean, comfortable and communication with the owner was excellent!I highly recommend if you’re looking for a wonderful get away."
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Carefree Lakefront Cottage/ 11 mins to skiing

10.0 out of 10, Exceptional, (203)
"Hopefully we'll be able to make it back when it's warmer beautiful "
Carefree Lakefront Cottage/ 11 mins to skiing

Live & Love Life on the Lake at Sunset Cottage!

9.6 out of 10, Exceptional, (51)
"Very relaxing, nice property. "
The price is AU$382
includes taxes & fees
2 Sept - 3 Sept
Live & Love Life on the Lake at Sunset Cottage!

Quaint cozy cottage nestled on the quiet shores of Pigeon Lake in Howe

2.0 star property
10.0 out of 10, Exceptional, (24)
"Beautiful view. My family enjoyed kayaking on the lake. "
Quaint cozy cottage nestled on the quiet shores of Pigeon Lake in Howe

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

9.6 out of 10, Exceptional, (19)
"Debi was great and my son and I enjoyed fishing off of a paddle boat we rented."
Perfect couple's retreat or family getaway less than an hour from Lake Michigan!

Newly Remodeled Cabin Steps from Sylvan Lake

10.0 out of 10, Exceptional, (43)
"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. "
Newly Remodeled Cabin Steps from Sylvan Lake

Emma's Place

10.0 out of 10, Exceptional, (53)
"This is a beautiful house. Very clean nice fenced in back yard. Real quiet location. Host is very friendly. We will stay here again if it is available our next trip back."
The price is AU$498
includes taxes & fees
2 Sept - 3 Sept
Emma's Place

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (156)
"It was a nice spot, near to the events we took in, over the weekend."
Charming farmhouse in peaceful countryside

Millie's Cottage

10.0 out of 10, Exceptional, (265)
"Very clean, cozy, and a great location!! Great communication with the host!We enjoyed our stay very much!! Highly recommend!!"
The price is AU$328
includes taxes & fees
28 Sept - 29 Sept
Millie's Cottage

Rest & Relaxation

10.0 out of 10, Exceptional, (12)
"We were able to enjoy a few days in a serene environment. The cabin was cozy and comfortable and our hosts were friendly and responsive. The hosts were actually one of the highlights of the stay! "
Rest & Relaxation

Cozy, Relaxing, Romantic, Fun All Sports Lake Cottage in Southwest Michigan

2.0 star property
10.0 out of 10, Exceptional, (6)
Cozy, Relaxing, Romantic, Fun All Sports Lake Cottage in Southwest Michigan

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

9.8 out of 10, Exceptional, (28)
"House was very clean, well stocked and a beautiful location. Easy access to town as well. Loved our stay!!!"
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

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

10.0 out of 10, Exceptional, (6)
"Place is beautiful "
Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi

Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!

9.2 out of 10, Wonderful, (20)
"My family enjoyed this property. Very spacious and plenty to do. Could use many updates. Has great potential to be a beautiful property. Owner responds quickly if needed when staying at property. Overall would stay again. "
Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

10.0 out of 10, Exceptional, (1)
"Very nice property clean nicely decorated very nice for the couple nights that we stayed there. I would recommend it highly"
The price is AU$513
includes taxes & fees
1 Sept - 2 Sept
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!

8.6 out of 10, Excellent, (9)
"Hard to find other than that it is a great stay"
The price is AU$187
includes taxes & fees
8 Sept - 9 Sept
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
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

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 favourite 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 depend 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 AU$187 per night. Entering your travel dates in the search wizard might find you 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?

Emma's Place: This holiday home rental outside of Middlebury offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals will I find in Middlebury?

With 16 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 Hunter 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.