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Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Middlebury

Family Cottage, 3 Bedrooms, Non Smoking, Lake View | Lake view
The Wellington Cottage

Cottage in Middlebury

3.0 star property
10.0 out of 10, Exceptional, (5)
"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
$60 nightly
The price is $69
Dec 7 - Dec 8
Total with taxes and fees
The Wellington Cottage
Property grounds
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Cottage in Middlebury

2.0 star property
10.0 out of 10, Exceptional, (41)
"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
Dec 14 - Dec 15
Total with taxes and fees
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Smart TV, DVD player
Hidden Log Cabin | Hot Tub | Ping Pong | Family |

Vacation Home in Goshen

10.0 out of 10, Exceptional, (10)
"Such a lovely place!It was spotless and peaceful"
United States
Marilee G.
$270 nightly
The price is $272
Dec 10 - Dec 11
Total with taxes and fees
Hidden Log Cabin | Hot Tub | Ping Pong | Family |
Fridge, microwave, oven, stovetop
| Hot Tub | Amish Farm Country | Pergola | Deck |

Vacation Home in Middlebury

10.0 out of 10, Exceptional, (92)
"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.
$259 nightly
The price is $261
Dec 6 - Dec 7
Total with taxes and fees
| Hot Tub | Amish Farm Country | Pergola | Deck |
Outdoor spa tub
HOT TUB | Beautiful Backyard Oasis|Newly Renovated

Vacation Home in Middlebury

10.0 out of 10, Exceptional, (62)
"Nice, quiet place for a ladies weekend. Would recommend and stay here again."
United States
Stephanie K.
$257 nightly
The price is $260
Dec 9 - Dec 10
Total with taxes and fees
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Smart TV, books
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Vacation Home in Middlebury

10.0 out of 10, Exceptional, (25)
"House was nice & clean, enjoyed our stay!"
United States
Delmer Y.
$299 nightly
The price is $320
Dec 20 - Dec 21
Total with taxes and fees
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
House | 2 bedrooms
Farm Country Amish Country Newly Renovated

Vacation Home in Middlebury

2.0 star property
$253 nightly
The price is $271
Dec 6 - Dec 7
Total with taxes and fees
Farm Country Amish Country Newly Renovated
House (2 Bedrooms) | Interior
Cassopolis Cabin, Little Fish Lake On-site!

Cottage in Cassopolis

3.0 star property
$236 nightly
The price is $250
Dec 7 - Dec 8
Total with taxes and fees
Cassopolis Cabin, Little Fish Lake On-site!
Microwave, oven, stovetop
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Cottage in Syracuse

9.8 out of 10, Exceptional, (6)
"The cottage fits the description perfectly! It was probably the cleanest place I've ever stayed, which meant so much. It is as nice outside as in. Will definitely book again for a quiet weekend away."
United States
Ryan B.
$233 nightly
The price is $261
Dec 28 - Dec 29
Total with taxes and fees
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Outdoor dining
Live & Love Life on the Lake at Sunset Cottage!

Cottage in Howe

9.6 out of 10, Exceptional, (56)
"We love staying at Sunset Cottage! Peaceful, private vacation. Great nearby restaurants as well.Host Krista Mayo is wonderful!"
United States
Kim T.
$224 nightly
The price is $258
Dec 7 - Dec 8
Total with taxes and fees
Live & Love Life on the Lake at Sunset Cottage!
Interior
Welcome to our Home in Ligonier

Vacation 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!"
United States
Jeremiah A.
$217 nightly
The price is $243
Dec 5 - Dec 6
Total with taxes and fees
Welcome to our Home in Ligonier
Property grounds
Relax and unwind at the Cozy Cabin on Heaton Lake.

Cabin in Elkhart

2.0 star property
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.
$171 nightly
The price is $183
Dec 5 - Dec 6
Total with taxes and fees
Relax and unwind at the Cozy Cabin on Heaton Lake.
Smart TV, video games
Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!

Cabin in Goshen

9.6 out of 10, Exceptional, (16)
"This was an exceptional venue for my family, in town for a reunion. Lots of space, super clean, beautifully decorated, and located in the heart of Goshen. I would definitely recommend this cabin."
United States
Nancy R.
$267 nightly
The price is $285
Dec 7 - Dec 8
Total with taxes and fees
Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!
Outdoor dining
Lake House | Kayaks | Patio/Deck | Private Pier

Vacation Home in Rome City

2.0 star property
9.8 out of 10, Exceptional, (16)
"We enjoyed our time away"
United States
lori b.
$277 nightly
The price is $281
Dec 8 - Dec 9
Total with taxes and fees
Lake House | Kayaks | Patio/Deck | Private Pier
Fridge, microwave, oven, stovetop
Arrowhead Riverfront- 30 Min to ND Stadium

Cottage in Bristol

9.8 out of 10, Exceptional, (17)
"This is a great place to stay with a larger group, it was clean and comfortable. There was plenty of space for three generations of family. We shared meals around the huge dinning table, visited with friends and family and played a few games. We would definitely stay again in the future."
United States
betsy s.
$423 nightly
The price is $453
Dec 7 - Dec 8
Total with taxes and fees
Arrowhead Riverfront- 30 Min to ND Stadium
Fridge, microwave, oven, dishwasher
Cozy Lake House On The Channel With Access To 5 Lakes!

Vacation Home in Wolcottville

9.6 out of 10, Exceptional, (41)
"My 3 nieces and I book a trip every year and found this place. It was very cozy and relaxing. The host was communicative and nice. It was so great to be able to use the paddle boat and kayaks! The neighbors were also friendly. Overall Nice stay"
United States
Vallerie M.
$240 nightly
The price is $276
Dec 7 - Dec 8
Total with taxes and fees
Cozy Lake House On The Channel With Access To 5 Lakes!
TV, fireplace
Serendipity on Grey Lake - Sturgis, MI

Vacation Home in Sturgis

10.0 out of 10, Exceptional, (89)
"Beautiful property 1 night stay"
United States
Phyllis M.
$421 nightly
The price is $443
Dec 7 - Dec 8
Total with taxes and fees
Serendipity on Grey Lake - Sturgis, MI
Outdoor dining
A-Frame near Chicago, Notre Dame, Shipshewana, Pet friendly, Shared Hottub.

Vacation Home in Sturgis

2.0 star property
9.0 out of 10, Wonderful, (8)
"Cute, clean, and cozy. Leah was great. She was quick to respond to any questions I have. Thank you "
United States
Kunthy
$251 nightly
The price is $261
Dec 7 - Dec 8
Total with taxes and fees
A-Frame near Chicago, Notre Dame, Shipshewana, Pet friendly, Shared Hottub.
Property grounds
Kayaks | Relax by River | 10 Min to Shipshewana |

Vacation Home in Howe

10.0 out of 10, Exceptional, (22)
"We had a great stay. It was really clean and comfortable, and I loved being able to kayak. It was a perfect place for a relaxing few days."
United States
Christine C.
$220 nightly
The price is $224
Dec 5 - Dec 6
Total with taxes and fees
Kayaks | Relax by River | 10 Min to Shipshewana |
Outdoor pool
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Vacation Home in Milford

10.0 out of 10, Exceptional, (29)
"We had a really great time and the host was very very responsive to all our questions. "
United States
Mary B.
$326 nightly
The price is $365
Dec 5 - Dec 6
Total with taxes and fees
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
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

Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

10/10 Excellent
"Great staff Great room Clean pool/spa Great food Great service"
Nathan 1-night trip
Posted 1 day ago
Essenhaus Inn & Conference Center

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 $69 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.

Explore a world of travel with Expedia

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?

HOT TUB | Beautiful Backyard Oasis|Newly Renovated: Visitors like this Middlebury vacation home rental. It offers a patio, a selection of games, and a barbecue grill 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 you can cook with friends or family. Make the most of the 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 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, Meadow Valley Golf Club and Middlebury Public Library 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.