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Middlebury Vacation Rentals

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Our top choices for Middlebury vacation rentals

Cottage in Middlebury

The Wellington Cottage
3.0 star property
10.0 out of 10, Exceptional, (6)
"It had everything we needed was off the beaten path, we swam in the water and used the paddle boat, nice and relaxing"
United States
Susan
$71 nightly
The price is $82
Jan 12 - Jan 13
Total with taxes and fees
The Wellington Cottage
10.0 out of 10, Exceptional, (42)
"Very nice place a little into the countryside. Will definitely stay again next time I’m in the area."
United States
Brad
$135 nightly
The price is $144
Jan 11 - Jan 12
Total with taxes and fees
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
10.0 out of 10, Exceptional, (10)
"Such a lovely place!It was spotless and peaceful"
United States
Marilee G.
$225 nightly
The price is $227
Jan 12 - Jan 13
Total with taxes and fees
Hidden Log Cabin | Hot Tub | Ping Pong | Family |
10.0 out of 10, Exceptional, (93)
"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.
$215 nightly
The price is $217
Jan 8 - Jan 9
Total with taxes and fees
| Hot Tub | Amish Farm Country | Pergola | Deck |
10.0 out of 10, Exceptional, (62)
"Nice, quiet place for a ladies weekend. Would recommend and stay here again."
United States
Stephanie K.
$211 nightly
The price is $213
Jan 11 - Jan 12
Total with taxes and fees
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
10.0 out of 10, Exceptional, (26)
"Came up for a wedding and had a wonderful time with my friends. Thank you for being such great hosts! "
United States
Thomas B.
$310 nightly
The price is $331
Jan 8 - Jan 9
Total with taxes and fees
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
2.0 star property
$212 nightly
The price is $227
Jan 8 - Jan 9
Total with taxes and fees
Farm Country Amish Country Newly Renovated
2.0 star property
10.0 out of 10, Exceptional, (2)
"Very enjoyable stay."
United States
June P.
$237 nightly
The price is $273
Jan 8 - Jan 9
Total with taxes and fees
Little Luxe Retreat #7 | Tiny Home + Fire Table
2.0 star property
10.0 out of 10, Exceptional, (1)
"Host was great. Timely communications throughout our stay. The cabin was basically brand new and provided everything we needed. Nice location. Would stay again!"
United States
Calvin W.
$183 nightly
The price is $186
Jan 11 - Jan 12
Total with taxes and fees
Secluded Shipshewana Log Cabin | In the Woods |
3.0 star property
$236 nightly
The price is $250
Jan 11 - Jan 12
Total with taxes and fees
Cassopolis Cabin, Little Fish Lake On-site!
9.6 out of 10, Exceptional, (56)
"beautiful cottage that's conveniently close to several tourism hubs . we had a blast "
United States
Austin S.
$203 nightly
The price is $233
Jan 8 - Jan 9
Total with taxes and fees
Live & Love Life on the Lake at Sunset Cottage!
10.0 out of 10, Exceptional, (24)
"This was a convenient option over hotel while we were in town. "
United States
Nancy K.
$171 nightly
The price is $183
Jan 8 - Jan 9
Total with taxes and fees
Relax and unwind at the Cozy Cabin on Heaton Lake.
10.0 out of 10, Exceptional, (4)
"Incredible stay. They’ve thought of everything you would need for an enjoyable and relaxing vacation. A dream cottage. "
United States
Larry
$239 nightly
The price is $243
Jan 11 - Jan 12
Total with taxes and fees
Lake House | Shallow Sandy | Kayaks | Family Fun
10.0 out of 10, Exceptional, (1)
"Property was beautiful and fantastic. Easy to deal with. "
United States
Anonymous traveler
$769 nightly
The price is $862
Jan 8 - Jan 9
Total with taxes and fees
Hilltop Haven 1BR Lakefront Home – Private Island, Hot Tub, Kayaks & Pool Table
9.0 out of 10, Wonderful, (14)
"We were looking for a place off the beaten path with plenty of privacy and this locstion provided both. The hosts were fantastic and we had a great time. "
United States
Trevor W.
$115 nightly
The price is $120
Jan 8 - Jan 9
Total with taxes and fees
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
9.8 out of 10, Exceptional, (7)
"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. "
United States
Ty M.
$233 nightly
The price is $261
Jan 8 - Jan 9
Total with taxes and fees
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
10.0 out of 10, Exceptional, (29)
"We very much enjoyed our stay. The pool and hot tub were amazing and the home was thoughtfully prepared. We would definitely love to stay here again. "
United States
Mariah C.
$315 nightly
The price is $353
Jan 8 - Jan 9
Total with taxes and fees
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Cabin in Marcellus

Winding Creek Cabins
10.0 out of 10, Exceptional, (8)
"Very clean and comfortable. Great view of nature"
United States
Keith M.
$225 nightly
The price is $236
Jan 8 - Jan 9
Total with taxes and fees
Winding Creek Cabins

Vacation Home in Elkhart

The Gemini
9.2 out of 10, Wonderful, (13)
"We have friends that live close. This was the perfect location for a weekend visit."
United States
Rhonda R.
$136 nightly
The price is $146
Jan 8 - Jan 9
Total with taxes and fees
The Gemini
2.0 star property
10.0 out of 10, Exceptional, (7)
"It was a fantastic comfortable house to continue a long standing tradition if visitong Lake Wawasee. Nice being so close to the Frog Tavern."
United States
Mike H.
$222 nightly
The price is $249
Jan 12 - Jan 13
Total with taxes and fees
Lake Wawasee FROG House, Surround Sound & Bikes
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 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 $82 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.

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?

The Back Porch Haven Stay in Amish Country yet close to Notre Dame: Visitors like this Middlebury vacation home rental. It is located in a rural location and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Some other homes for rent in Middlebury include HOT TUB | Beautiful Backyard Oasis|Newly Renovated and Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame..

How many vacation rentals will I find in Middlebury?

With 15 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 Trout Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Deutsch Kase Haus. While here, Middlebury Community Historical and Meadow Valley Golf Club 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.