Holiday Rentals in Middlebury

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Our top choices for Middlebury holiday rentals

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

| 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 €187
includes taxes & fees
17 Feb - 18 Feb
| Hot Tub | Amish Farm Country | Pergola | Deck |

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 €126
includes taxes & fees
17 Feb - 18 Feb
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

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 €266
includes taxes & fees
17 Feb - 18 Feb
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

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 €317
includes taxes & fees
17 Feb - 18 Feb
Charming 3-bedroom house located on Main Street in Downtown Middlebury

Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is €196
includes taxes & fees
17 Feb - 18 Feb
Farm Country Amish Country Newly Renovated

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 €198
includes taxes & fees
17 Feb - 18 Feb
Live & Love Life on the Lake at Sunset Cottage!

Kayaks | Relax by River | 10 Min to Shipshewana |

Kayaks | Relax by River | 10 Min to Shipshewana |
Howe
10.0 out of 10, Exceptional, (22 reviews)
"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.
The price is €157
includes taxes & fees
17 Feb - 18 Feb
Kayaks | Relax by River | 10 Min to Shipshewana |

Millie's Cottage

Millie's Cottage
Shipshewana
10.0 out of 10, Exceptional, (279 reviews)
"Clean, comfortable, great area. Easy to work with owner, always enjoy staying at Millie’s cottage."
United States
Terry K.
The price is €173
includes taxes & fees
17 Feb - 18 Feb
Millie's Cottage

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 €156
includes taxes & fees
17 Feb - 18 Feb
Relax and unwind at the Cozy Cabin on Heaton Lake.

Cassopolis Cabin, Little Fish Lake On-site!

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
Cassopolis
The price is €211
includes taxes & fees
18 Feb - 19 Feb
Cassopolis Cabin, Little Fish Lake On-site!

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 €299
includes taxes & fees
17 Feb - 18 Feb
Emma's Place

Live & Love Life on the Lake at Sunset Peak!

Live & Love Life on the Lake at Sunset Peak!
Howe
9.8 out of 10, Exceptional, (28 reviews)
"Quiet, calm, and plenty of room. "
United States
Aaron H.
The price is €260
includes taxes & fees
17 Feb - 18 Feb
Live & Love Life on the Lake at Sunset Peak!

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 €129
includes taxes & fees
17 Feb - 18 Feb
Charming farmhouse in peaceful countryside

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 €164
includes taxes & fees
18 Feb - 19 Feb
Secluded Shipshewana Log Cabin | In the Woods |

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 €172
includes taxes & fees
17 Feb - 18 Feb
Woodside Retreat in the Heart of Amish Country

Lake Retreat With Hot Tub

Lake Retreat With Hot Tub
Howe
9.8 out of 10, Exceptional, (31 reviews)
"Thank you so much for your wonderful hospitality! My wife and I had a great stay at the Cozy Nest. It was comfortable and had everything we needed for a relaxing getaway. We would defiantly love to stay again."
United States
Steve R.
The price is €155
includes taxes & fees
19 Feb - 20 Feb
Lake Retreat With Hot Tub

Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife

Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife
Vandalia
10.0 out of 10, Exceptional, (74 reviews)
"Very nice, and very clean, we enjoyed our stay "
United States
Steve
The price is €206
includes taxes & fees
18 Feb - 19 Feb
Hot Tub, Couples Hideaway, Private, Gazebo, Serene, Country, Birds, Wildlife

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 €105
includes taxes & fees
17 Feb - 18 Feb
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!

Lake House | Shallow Sandy | Kayaks | Family Fun

Lake House | Shallow Sandy | Kayaks | Family Fun
Middlebury
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 €215
includes taxes & fees
17 Feb - 18 Feb
Lake House | Shallow Sandy | Kayaks | Family Fun
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlebury holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury holiday rentals we have selected for you start as low as €126 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury holiday 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 holiday.

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 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?

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.: This highly rated holiday home rental in Middlebury is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Middlebury?

With 13 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 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 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.