Photo by Ann Sair

Middlebury Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Middlebury holiday rentals

Lake view
The Wellington Cottage

Cottage in Middlebury

The Wellington Cottage
3.0 star property
10.0 out of 10, Exceptional, (6 reviews)
"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
The Wellington Cottage
Property grounds
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Cottage in Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
2.0 star property
10.0 out of 10, Exceptional, (42 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 HK$895
HK$1,125 total
includes taxes & fees
15 Jan - 16 Jan
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Smart TV, DVD player
Hidden Log Cabin | Hot Tub | Ping Pong | Family |

Holiday Home in Goshen

Hidden Log Cabin | Hot Tub | Ping Pong | Family |
10.0 out of 10, Exceptional, (10 reviews)
"Such a lovely place!It was spotless and peaceful"
United States
Marilee G.
The price is HK$636
HK$1,766 total
includes taxes & fees
12 Jan - 13 Jan
Hidden Log Cabin | Hot Tub | Ping Pong | Family |
Outdoor spa tub
| Hot Tub | Amish Farm Country | Pergola | Deck |

Holiday Home in Middlebury

| Hot Tub | Amish Farm Country | Pergola | Deck |
10.0 out of 10, Exceptional, (93 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 HK$609
HK$1,692 total
includes taxes & fees
12 Jan - 13 Jan
| Hot Tub | Amish Farm Country | Pergola | Deck |
Outdoor spa tub
HOT TUB | Beautiful Backyard Oasis|Newly Renovated

Holiday Home in Middlebury

HOT TUB | Beautiful Backyard Oasis|Newly Renovated
10.0 out of 10, Exceptional, (62 reviews)
"Nice, quiet place for a ladies weekend. Would recommend and stay here again."
United States
Stephanie K.
The price is HK$663
HK$1,659 total
includes taxes & fees
11 Jan - 12 Jan
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Smart TV, books
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Holiday Home in Middlebury

The Back Porch Haven Stay in Amish Country yet close to Notre Dame
10.0 out of 10, Exceptional, (26 reviews)
"Came up for a wedding and had a wonderful time with my friends. Thank you for being such great hosts! "
United States
Thomas B.
The price is HK$1,087
HK$2,580 total
includes taxes & fees
11 Jan - 12 Jan
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
2 bedrooms
Farm Country Amish Country Newly Renovated

Holiday Home in Middlebury

Farm Country Amish Country Newly Renovated
2.0 star property
The price is HK$702
HK$1,797 total
includes taxes & fees
12 Jan - 13 Jan
Farm Country Amish Country Newly Renovated
Exterior
Little Luxe Retreat #7 | Tiny Home + Fire Table

Holiday Home in Shipshewana

Little Luxe Retreat #7 | Tiny Home + Fire Table
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Very enjoyable stay."
United States
June P.
The price is HK$720
HK$1,867 total
includes taxes & fees
10 Jan - 11 Jan
Little Luxe Retreat #7 | Tiny Home + Fire Table
Smart TV
Secluded Shipshewana Log Cabin | In the Woods |

Apartment in Shipshewana

Secluded Shipshewana Log Cabin | In the Woods |
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"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.
The price is HK$609
HK$1,451 total
includes taxes & fees
13 Jan - 14 Jan
Secluded Shipshewana Log Cabin | In the Woods |
Interior
Cassopolis Cabin, Little Fish Lake On-site!

Cottage in Cassopolis

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
The price is HK$1,145
HK$1,945 total
includes taxes & fees
18 Jan - 19 Jan
Cassopolis Cabin, Little Fish Lake On-site!
Outdoor dining
Live & Love Life on the Lake at Sunset Cottage!

Cottage in Howe

Live & Love Life on the Lake at Sunset Cottage!
9.6 out of 10, Exceptional, (56 reviews)
"beautiful cottage that's conveniently close to several tourism hubs . we had a blast "
United States
Austin S.
The price is HK$736
HK$1,824 total
includes taxes & fees
11 Jan - 12 Jan
Live & Love Life on the Lake at Sunset Cottage!
Property grounds
Relax and unwind at the Cozy Cabin on Heaton Lake.

Cabin in Elkhart

Relax and unwind at the Cozy Cabin on Heaton Lake.
2.0 star property
10.0 out of 10, Exceptional, (24 reviews)
"This was a convenient option over hotel while we were in town. "
United States
Nancy K.
The price is HK$771
HK$1,416 total
includes taxes & fees
18 Jan - 19 Jan
Relax and unwind at the Cozy Cabin on Heaton Lake.
Property grounds
Lake House | Shallow Sandy | Kayaks | Family Fun

Holiday Home in Middlebury

Lake House | Shallow Sandy | Kayaks | Family Fun
10.0 out of 10, Exceptional, (4 reviews)
"Incredible stay. They’ve thought of everything you would need for an enjoyable and relaxing vacation. A dream cottage. "
United States
Larry
The price is HK$636
HK$1,891 total
includes taxes & fees
11 Jan - 12 Jan
Lake House | Shallow Sandy | Kayaks | Family Fun
Property grounds
Hilltop Haven 1BR Lakefront Home – Private Island, Hot Tub, Kayaks & Pool Table

Holiday Home in Rome City

Hilltop Haven 1BR Lakefront Home – Private Island, Hot Tub, Kayaks & Pool Table
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Property was beautiful and fantastic. Easy to deal with. "
United States
Anonymous traveller
The price is HK$5,215
HK$6,670 total
includes taxes & fees
10 Jan - 11 Jan
Hilltop Haven 1BR Lakefront Home – Private Island, Hot Tub, Kayaks & Pool Table
Interior
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!

Cabin in Marcellus

Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
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 HK$662
HK$935 total
includes taxes & fees
9 Feb - 10 Feb
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
Terrace/patio
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Cottage in Syracuse

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
9.8 out of 10, Exceptional, (7 reviews)
"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.
The price is HK$1,004
HK$1,988 total
includes taxes & fees
19 Jan - 20 Jan
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Terrace/patio
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Holiday Home in Milford

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
10.0 out of 10, Exceptional, (29 reviews)
"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.
The price is HK$975
HK$2,750 total
includes taxes & fees
10 Jan - 11 Jan
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Exterior
Winding Creek Cabins

Cabin in Marcellus

Winding Creek Cabins
10.0 out of 10, Exceptional, (8 reviews)
"Very clean and comfortable. Great view of nature"
United States
Keith M.
The price is HK$1,394
HK$1,860 total
includes taxes & fees
10 Jan - 11 Jan
Winding Creek Cabins
Living area
The Gemini

Holiday Home in Elkhart

The Gemini
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 HK$905
HK$1,135 total
includes taxes & fees
10 Jan - 11 Jan
The Gemini
Interior
Lake Wawasee FROG House, Surround Sound & Bikes

Holiday Home in Syracuse

Lake Wawasee FROG House, Surround Sound & Bikes
2.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"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.
The price is HK$1,121
HK$1,936 total
includes taxes & fees
12 Jan - 13 Jan
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

avid Hotels Elkhart North by IHG

avid Hotels Elkhart North by IHG

10/10 Excellent
"Always a great stay."
marco 1-night trip
Posted 3 days ago
avid Hotels Elkhart North by IHG

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 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?

The Back Porch Haven Stay in Amish Country yet close to Notre Dame: This highly rated holiday home rental in Middlebury is located in a rural location, and has a patio, a selection of games and a BBQ 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 that 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 holiday rentals will I find in Middlebury?

With 15 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 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 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.