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Middlebury Vacation Rentals

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Oct 10 - Oct 12
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Oct 24 - Oct 26
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Dec 19 - Dec 21

Vacation Rentals in Middlebury

Our top choices for Middlebury vacation rentals

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

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

10.0 out of 10, Exceptional, (5)
"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! "
Charming 3-bedroom house located on Main Street in Downtown Middlebury
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Property grounds

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

2.0 star property
10.0 out of 10, Exceptional, (31)
"Would definitely come back!"
The price is ￥16,975
￥21,322 total
includes taxes & fees
Oct 7 - Oct 8
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
The Wellington Cottage
Family Cottage, 3 Bedrooms, Non Smoking, Lake View | Lake view

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
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Outdoor spa tub

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (60)
"Very clean, nicely appointed. Ping pong table and hot tub were a real bonus! "
The price is ￥22,249
￥41,960 total
includes taxes & fees
Oct 5 - Oct 6
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Smart TV, books

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 ￥20,984
￥48,886 total
includes taxes & fees
Oct 26 - Oct 27
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.
Outdoor dining

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

9.8 out of 10, Exceptional, (22)
"House was very clean. Great view of lake. "
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
The Loft 3BR Apartment with Scenic Deck
Fridge, microwave, oven, coffee/tea maker

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 ￥21,848
￥69,498 total
includes taxes & fees
Sep 28 - Sep 29
The Loft 3BR Apartment with Scenic Deck
Carefree Lakefront Cottage/ 11 mins to skiing
Terrace/patio

Carefree Lakefront Cottage/ 11 mins to skiing

10.0 out of 10, Exceptional, (205)
"Such a great little place! I could live there!!!!! Would stay again!!"
Carefree Lakefront Cottage/ 11 mins to skiing
Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi
Interior

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

10.0 out of 10, Exceptional, (8)
"Place is beautiful "
Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi
Live & Love Life on the Lake at Sunset Cottage!
Outdoor dining

Live & Love Life on the Lake at Sunset Cottage!

9.6 out of 10, Exceptional, (53)
"Very relaxing, nice property. "
The price is ￥16,606
￥39,128 total
includes taxes & fees
Sep 28 - Sep 29
Live & Love Life on the Lake at Sunset Cottage!
Perfect couple's retreat or family getaway less than an hour from Lake Michigan!
Exterior

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

9.6 out of 10, Exceptional, (20)
"Simple and restful accommodations imbedded in nature! Debi was super nice as well!"
Perfect couple's retreat or family getaway less than an hour from Lake Michigan!
Beautiful Waterfront Home on Baugo Bay
Fridge, microwave, oven, stovetop

Beautiful Waterfront Home on Baugo Bay

9.6 out of 10, Exceptional, (34)
"Great stay and great host!"
The price is ￥73,805
￥96,928 total
includes taxes & fees
Sep 29 - Sep 30
Beautiful Waterfront Home on Baugo Bay
Newly renovated 2-bedroom Lakehouse in Edwardsburg - 11 miles from ND
Marina

Newly renovated 2-bedroom Lakehouse in Edwardsburg - 11 miles from ND

10.0 out of 10, Exceptional, (3)
"This Lakehouse was awesome!! Would recommended it to anyone visiting Notre Dame.Love love love Also, the owner was 5*, super nice and super helpful. "
Newly renovated 2-bedroom Lakehouse in Edwardsburg - 11 miles from ND
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
Outdoor spa tub

Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

10.0 out of 10, Exceptional, (118)
"Well appointed cottage, clean and quiet. We enjoyed our stay."
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
Newly Remodeled Cabin Steps from Sylvan Lake
Dining

Newly Remodeled Cabin Steps from Sylvan Lake

10.0 out of 10, Exceptional, (45)
"We have a great stay. House was clean and comfortable. "
Newly Remodeled Cabin Steps from Sylvan Lake
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.
Property grounds

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

9.8 out of 10, Exceptional, (30)
"We had a lovely time in Shipshewana. The rental was very nice, and very comfortable. "
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.
Woodside Retreat in the Heart of Amish Country
Dining

Woodside Retreat in the Heart of Amish Country

10.0 out of 10, Exceptional, (8)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
The price is ￥16,975
￥29,535 total
includes taxes & fees
Sep 28 - Sep 29
Woodside Retreat in the Heart of Amish Country
Beautiful Private Setting !!!
Exterior

Beautiful Private Setting !!!

10.0 out of 10, Exceptional, (22)
"We had a fabulous time! The home is discuss and great for spending time together. Thanks Linda for a wonderful stay!"
The price is ￥31,751
￥60,350 total
includes taxes & fees
Sep 28 - Sep 29
Beautiful Private Setting !!!
Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!
Blender, cookware/dishes/utensils, paper towels, dining tables

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

9.2 out of 10, Wonderful, (21)
"Great property for our large group. Plenty to do with an indoor and outdoor pool, an indoor gym with basketball and pickle ball court and a hot tub. Plenty of space with eight queen size beds, two refrigerators and two living rooms with televisions. The group enjoyed the secluded property located in a neighborhood. Also loved the wildlife (rabbits, squirrels, groundhogs and birds) that shared the property."
Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
Outdoor dining

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 ￥12,547
￥17,728 total
includes taxes & fees
Sep 26 - Sep 27
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

Travelodge by Wyndham Elkhart

Travelodge by Wyndham Elkhart

10/10 Excellent
"Affordable, modern, clean and safe. Great option for Notre Dame Football games lodging "
Simona 3-night trip
Posted 2 days ago
Travelodge by Wyndham Elkhart

Find out more about Middlebury

Find out more about Middlebury

Search for holiday rentals in Middlebury on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlebury using one of the methods below:

  • View our selection of featured holiday rentals in Middlebury
  • Use the map to find apartments and other holiday homes in the Middlebury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlebury while they last

Look no further and take a look at our great range of rental properties in Middlebury!

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?

Charming 3-bedroom house located on Main Street in Downtown Middlebury: Visitors like this Middlebury vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals will I find in Middlebury?

With 17 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 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 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.