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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
10.0 out of 10, Exceptional, (35)
"We were very happy with our stay! Everything was very clean! Communication was very prompt and friendly! Will definately keep in mind for next year!"
The price is AU$225
includes taxes & fees
19 Oct - 20 Oct
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
The Wellington Cottage
3.0 star property
10.0 out of 10, Exceptional, (3)
"It had everything we needed was off the beaten path, we swam in the water and used the paddle boat, nice and relaxing"
The Wellington Cottage
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
10.0 out of 10, Exceptional, (24)
"House was nice & clean, enjoyed our stay!"
The price is AU$506
includes taxes & fees
27 Oct - 28 Oct
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
The Loft 3BR Apartment with Scenic Deck
6.0 out of 10, (1)
"Okay, we came after it had snow a few days prior and nothing was cleared on the many steps nor ramp path, so 6 of us trudged thru snow then tracked snow up wooden stairs that really need some type of padding. NOT for elderly or anyone with steps problems.The 3 beds were so uncomfortable, squeaky and thin; I was able to can feel the mattress quilting through the sheets.The decorative pillow in my bedroom, smelled happily of someone’s cologne.Not impressed at all. Not terrible, but no screens in...
The price is AU$726
includes taxes & fees
19 Oct - 20 Oct
The Loft 3BR Apartment with Scenic Deck
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
9.0 out of 10, Wonderful, (12)
"Hard to find other than that it is a great stay"
The price is AU$187
includes taxes & fees
27 Oct - 28 Oct
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
Welcome to our Home in Ligonier
2.0 star property
10.0 out of 10, Exceptional, (2)
"This is our third time renting this property. The hosts are awesome and pay attention to detail. Couldn't be happier with our stay!"
The price is AU$377
includes taxes & fees
15 Nov - 16 Nov
Welcome to our Home in Ligonier
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
10.0 out of 10, Exceptional, (3)
"Great clean little cabin by the lake. Hot tub and outdoor area is nice! Very private with a view of the water on the porch. "
The price is AU$515
includes taxes & fees
19 Oct - 20 Oct
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Live & Love Life on the Lake at Sunset Cottage!
9.6 out of 10, Exceptional, (55)
"It was an adorable cottage, enjoyed the fishing, kayak & paddle boards."
The price is AU$429
includes taxes & fees
20 Oct - 21 Oct
Live & Love Life on the Lake at Sunset Cottage!
The Gemini
8.8 out of 10, Excellent, (10)
"We have friends that live close. This was the perfect location for a weekend visit."
The price is AU$191
includes taxes & fees
27 Oct - 28 Oct
The Gemini
Lake Front Cottage | Kayaks | Game Table Fun
10.0 out of 10, Exceptional, (4)
"The house was immaculate and absolutely perfect for our weekend away. Easy access to shopping and restaurants."
The price is AU$302
includes taxes & fees
28 Oct - 29 Oct
Lake Front Cottage | Kayaks | Game Table Fun
Serendipity on Grey Lake - Sturgis, MI
10.0 out of 10, Exceptional, (87)
"Property was perfect, clean and comfortable. Lake fishing was good, paddle boards fun as well. Kitchen was stocked well."
The price is AU$761
includes taxes & fees
20 Oct - 21 Oct
Serendipity on Grey Lake - Sturgis, MI
Cottages on Sand Lake - The Cozy Cottage
9.2 out of 10, Wonderful, (20)
"It worked fine for us for a very winter getaway and is close to Shipshawana which is what I wanted. It is cosy so if you are looking for something spacious not the place. "
The price is AU$370
includes taxes & fees
19 Oct - 20 Oct
Cottages on Sand Lake - The Cozy Cottage
Emma's Place
10.0 out of 10, Exceptional, (54)
"Enjoyed our stay! Would definitely stay here again."
The price is AU$496
includes taxes & fees
22 Oct - 23 Oct
Emma's Place
Woodside Retreat in the Heart of Amish Country
10.0 out of 10, Exceptional, (9)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
The price is AU$311
includes taxes & fees
26 Oct - 27 Oct
Woodside Retreat in the Heart of Amish Country
Choo Choo Inn
10.0 out of 10, Exceptional, (25)
"The Cho Cho Inn was perfect. The home was very clean and had very thoughtful details throughout. I really appreciate the host being accommodating with our check in process. We will definitely stay here again and would highly recommend for others. "
The price is AU$343
includes taxes & fees
20 Oct - 21 Oct
Choo Choo Inn
Cottages on Sand Lake - The Lazy Lakehouse
9.8 out of 10, Exceptional, (13)
"Beautiful property and wonderful property owner. We loved staying here. The cabin was clean and very comfortable. We look forward to staying there again."
The price is AU$372
includes taxes & fees
29 Oct - 30 Oct
Cottages on Sand Lake - The Lazy Lakehouse
Cozy little lake cottage on Buck Lake!
10.0 out of 10, Exceptional, (11)
"Great property! We had such a good time!"
The price is AU$421
includes taxes & fees
27 Oct - 28 Oct
Cozy little lake cottage on Buck Lake!
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
10.0 out of 10, Exceptional, (29)
"The stay was just arpund the corber from our home but felt like a getaway!"
The price is AU$569
includes taxes & fees
20 Oct - 21 Oct
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!
9.4 out of 10, Exceptional, (12)
"Love all the antiques and the look of the cabin. "
The price is AU$513
includes taxes & fees
26 Oct - 27 Oct
Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!
Tippecanoe Lakefront Classic Cottage
The price is AU$696
includes taxes & fees
21 Oct - 22 Oct
Tippecanoe Lakefront Classic 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

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$225 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 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 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.