Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Middlebury vacation rentals

Terrace/patio

The Wellington Cottage

The Wellington Cottage
3.0 star property
Middlebury
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful views "
United States
Darwin
The Wellington Cottage
Property grounds

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

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Middlebury
10.0 out of 10, Exceptional, (43 reviews)
"Very nice place a little into the countryside. Will definitely stay again next time I’m in the area."
United States
Brad
The price is ￥17,957
￥22,556 total
includes taxes & fees
Feb 22 - Feb 23
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Outdoor spa tub

| Hot Tub | Amish Farm Country | Pergola | Deck |

| Hot Tub | Amish Farm Country | Pergola | Deck |
Middlebury
10.0 out of 10, Exceptional, (94 reviews)
"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.
The price is ￥12,837
￥34,337 total
includes taxes & fees
Feb 11 - Feb 12
| Hot Tub | Amish Farm Country | Pergola | Deck |
Smart TV, books

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

The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Middlebury
10.0 out of 10, Exceptional, (27 reviews)
"We had a nice stay with our grandchildren. The house was a very nice space and clean. Our host was friendly and helpful. We loved watching the changing leaves in the yard."
United States
Monica G.
The price is ￥19,668
￥49,475 total
includes taxes & fees
Feb 11 - Feb 12
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
House | 2 bedrooms

Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is ￥13,920
￥34,745 total
includes taxes & fees
Feb 11 - Feb 12
Farm Country Amish Country Newly Renovated
Exterior

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

Charming 3-bedroom house located on Main Street in Downtown Middlebury
Middlebury
9.4 out of 10, Exceptional, (13 reviews)
"This was such a cute place, and the beds were so comfortable! My family and I loved staying here!"
United States
Tiffany E.
The price is ￥33,645
￥59,552 total
includes taxes & fees
Feb 12 - Feb 13
Charming 3-bedroom house located on Main Street in Downtown Middlebury
Outdoor dining

Live & Love Life on the Lake at Sunset Cottage!

Live & Love Life on the Lake at Sunset Cottage!
Howe
9.6 out of 10, Exceptional, (57 reviews)
"We had a great time staying here! The view of the lake was gorgeous and it was a very relaxing place to stay. "
United States
Katie H.
The price is ￥14,150
￥36,161 total
includes taxes & fees
Feb 15 - Feb 16
Live & Love Life on the Lake at Sunset Cottage!
Smart TV

Secluded Shipshewana Log Cabin | In the Woods |

Secluded Shipshewana Log Cabin | In the Woods |
Shipshewana
10.0 out of 10, Exceptional, (3 reviews)
"This is a delightful little cabin on the outskirts of town. It is so cozy and inviting. We thoroughly enjoyed our stay and would definitely stay again. "
United States
Danessa R.
The price is ￥16,091
￥34,336 total
includes taxes & fees
Feb 18 - Feb 19
Secluded Shipshewana Log Cabin | In the Woods |
Property grounds

Relax and unwind at the Cozy Cabin on Heaton Lake.

Relax and unwind at the Cozy Cabin on Heaton Lake.
Elkhart
10.0 out of 10, Exceptional, (25 reviews)
"This was a convenient option over hotel while we were in town. "
United States
Nancy K.
The price is ￥15,565
￥28,430 total
includes taxes & fees
Feb 15 - Feb 16
Relax and unwind at the Cozy Cabin on Heaton Lake.
Interior

Lake Front Cottage | Kayaks | Game Table Fun

Lake Front Cottage | Kayaks | Game Table Fun
Shipshewana
10.0 out of 10, Exceptional, (4 reviews)
"The house was immaculate and absolutely perfect for our weekend away. Easy access to shopping and restaurants."
United States
Brian C.
The price is ￥11,571
￥26,979 total
includes taxes & fees
Feb 11 - Feb 12
Lake Front Cottage | Kayaks | Game Table Fun
Interior

Woodside Retreat in the Heart of Amish Country

Woodside Retreat in the Heart of Amish Country
Nappanee
10.0 out of 10, Exceptional, (11 reviews)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
United States
VICKI
The price is ￥17,957
￥31,578 total
includes taxes & fees
Feb 18 - Feb 19
Woodside Retreat in the Heart of Amish Country
Interior

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

Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
Marcellus
9.0 out of 10, Wonderful, (14 reviews)
"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.
The price is ￥13,273
￥18,754 total
includes taxes & fees
Feb 20 - Feb 21
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
Living area

The Gemini

The Gemini
Elkhart
9.2 out of 10, Wonderful, (13 reviews)
"We have friends that live close. This was the perfect location for a weekend visit."
United States
Rhonda R.
The price is ￥18,129
￥22,740 total
includes taxes & fees
Feb 24 - Feb 25
The Gemini
Exterior

Little Luxe Retreat #7 | Tiny Home + Fire Table

Little Luxe Retreat #7 | Tiny Home + Fire Table
Shipshewana
10.0 out of 10, Exceptional, (2 reviews)
"Very enjoyable stay."
United States
June P.
The price is ￥14,527
￥37,679 total
includes taxes & fees
Feb 11 - Feb 12
Little Luxe Retreat #7 | Tiny Home + Fire Table
Terrace/patio

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

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Syracuse
9.8 out of 10, Exceptional, (7 reviews)
"The hot tub was clean and ready to go as soon as we got there.. very relaxing stay… we loved it"
United States
Samantha T.
The price is ￥20,143
￥40,749 total
includes taxes & fees
Feb 11 - Feb 12
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Interior

Cassopolis Cabin, Little Fish Lake On-site!

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
Cassopolis
The price is ￥22,954
￥39,011 total
includes taxes & fees
Feb 11 - Feb 12
Cassopolis Cabin, Little Fish Lake On-site!
Fridge, microwave, oven, stovetop

Charming farmhouse in peaceful countryside

Charming farmhouse in peaceful countryside
Nappanee
10.0 out of 10, Exceptional, (170 reviews)
"It was a clean nice place to stay. We loved the ping pong table. "
United States
Tracy M.
The price is ￥13,913
￥23,241 total
includes taxes & fees
Feb 18 - Feb 19
Charming farmhouse in peaceful countryside
Exterior detail

Emma's Place

Emma's Place
LaGrange
9.8 out of 10, Exceptional, (59 reviews)
"Enjoyed our stay! Would definitely stay here again."
United States
James S.
The price is ￥22,642
￥53,692 total
includes taxes & fees
Feb 24 - Feb 25
Emma's Place
Property grounds

Cottages on Sand Lake - The Cozy Cottage

Cottages on Sand Lake - The Cozy Cottage
Sturgis
9.2 out of 10, Wonderful, (23 reviews)
"It was a lovely get away"
United States
carol b.
Cottages on Sand Lake - The Cozy Cottage
Interior

Arrowhead Riverfront- 30 Min to ND Stadium

Arrowhead Riverfront- 30 Min to ND Stadium
Bristol
9.8 out of 10, Exceptional, (17 reviews)
"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.
The price is ￥30,705
￥71,210 total
includes taxes & fees
Feb 11 - Feb 12
Arrowhead Riverfront- 30 Min to ND Stadium
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

Blue Gate Garden Inn

Blue Gate Garden Inn

10/10 Excellent
"Great place to stay!!"
Lowell 1-night trip
Posted 2 days ago
Blue Gate Garden Inn

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
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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?

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.: Visitors like this Middlebury vacation home rental. It is located on a lake and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Middlebury?

With 14 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.