Photo by Ann Sair

Middlebury Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Middlebury

Smart TV, books
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
10.0 out of 10, Exceptional, (4)
"The place was very retro. We enjoyed our stay. Nice place to stay and lay your head. Very clean and accommodating."
The price is ￥21,979
￥50,898 total
includes taxes & fees
May 29 - May 30
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Property grounds
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
10.0 out of 10, Exceptional, (35)
"Loved it!"
The price is ￥17,407
￥37,816 total
includes taxes & fees
May 29 - May 30
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Property grounds
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, (5)
"Loved sitting on the deck, watching the boats & fishermen, sun coming up & going down. Loved the rise & shine donut’s, close to the Shipshewana Flea Market, just an an all around excellent time"
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Exterior
Recently renovated country cottage, 2.5 miles from Shipshewana
10.0 out of 10, Exceptional, (186)
"The house was so cute and the perfect size for us. We enjoyed watching the Amish with their buggy from the front porch. We went to the flea market and only covered about 1/3 of it. We will need to make another trip later this summer to cover the rest. Weather was perfect."
The price is ￥22,764
￥29,188 total
includes taxes & fees
May 30 - May 31
Recently renovated country cottage, 2.5 miles from Shipshewana
Pool
Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi
10.0 out of 10, Exceptional, (59)
"This was the perfect location to come back to after day trips to Shipshewana. It was very cute, comfortable and cozy. Our favorite part was the hot tub at night overlooking the peaceful and serene lake. We really enjoyed our stay."
Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi
Fridge, microwave, stovetop, coffee/tea maker
Cozy ‘Haven of Rest’ Home w/ Amish Country Views!
10.0 out of 10, Exceptional, (42)
"Idyllic. The owners were so helpful and friendly. Everything we needed was already there...and then some!!! Soooo close to everything and yet it fell so far removed from the busyness. Would love to come again."
Cozy ‘Haven of Rest’ Home w/ Amish Country Views!
Fridge, microwave, stovetop, dishwasher
Cozy Amish Country Cabin on Shipshewana Lake!
9.8 out of 10, Exceptional, (97)
"The only thing that didn't work was the electric fireplace downstairs, everything else was great. They even let me check in early which was nice. I would def stay again. Thanks."
Cozy Amish Country Cabin on Shipshewana Lake!
Fridge, microwave, oven, stovetop
Vacation at Garver Lake ~ Private Beach For Your Enjoyment!
8.2 out of 10, Very Good, (60)
"The cottage was wonderful!"
Vacation at Garver Lake ~ Private Beach For Your Enjoyment!
Property grounds
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
9.8 out of 10, Exceptional, (12)
"Very accommodating, quick responses to questions. Would definitely book again."
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
Pool
Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (112)
"Absolutely amazing place, very clean and quiet. Very well furnished especially in the kitchen. Everything you need to cook!"
The price is ￥20,409
￥28,557 total
includes taxes & fees
May 31 - Jun 1
Charming farmhouse in peaceful countryside
Property grounds
Beautiful Waterfront Home on Baugo Bay
10.0 out of 10, Exceptional, (21)
"We only stayed one night, good location, thanks for good communication as well."
The price is ￥78,495
￥102,907 total
includes taxes & fees
Jun 3 - Jun 4
Beautiful Waterfront Home on Baugo Bay
Fridge, microwave, oven, stovetop
Welcoming Grace College parents, fall weddings, traveling for work, or anything
9.8 out of 10, Exceptional, (9)
"Fantastic hosts! The home was super clean and had all the amenities we needed. It was a perfect location our events in Warsaw. We hope to be back next year!"
Welcoming Grace College parents, fall weddings, traveling for work, or anything
Fridge, oven, stovetop, coffee/tea maker
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.
9.4 out of 10, Exceptional, (19)
"We were looking for a small place near the lake for our small family (myself, wife and daughter). Clean, simple and on point with the description in the listing. Nice touches and some upgrades for an older cottage. It’s all we needed and very convenient to Oakwood Resort and the water. Would book again. Thanks!"
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.
Property grounds
Carefree Cottage on the Lake
10.0 out of 10, Exceptional, (154)
"Clean and neatly appointed. All the comforts of home. The neighbors stood out ... everyone waves, everyone smiles, kind of made us fall in love with Michigan. Lake life, seems like it really is the best life. Thank you for sharing your home with us."
Carefree Cottage on the Lake
Beach
Live & Love Life on the Lake!
9.6 out of 10, Exceptional, (21)
"We loved the small lake and also…what do you use on your towels? We want to get that!! The cottage is very comfy and loved all the ceiling fans as well."
The price is ￥23,392
￥47,826 total
includes taxes & fees
Jun 2 - Jun 3
Live & Love Life on the Lake!
Fridge, microwave, oven, dishwasher
Cozy Lake House On The Channel With Access To 5 Lakes!
9.8 out of 10, Exceptional, (18)
"The location was perfect to decompress after a long day."
The price is ￥23,549
￥40,265 total
includes taxes & fees
May 28 - May 29
Cozy Lake House On The Channel With Access To 5 Lakes!
Fridge, microwave, oven, stovetop
Emma's Place
10.0 out of 10, Exceptional, (26)
"Overnight stay to be able to attend Ship Chic in Shipshewana. Needed a place with 4 bedrooms for 4 adult females. Emma’s place fit the bill. Great communication, adorable house. Only issue was garage next door had roofers starting at 7:30 am and property owner has no control over that. We’re hoping to travel up that way again and would love to have a repeat stay at Emma’s Place"
The price is ￥23,549
￥49,233 total
includes taxes & fees
May 29 - May 30
Emma's Place
Exterior
Rocky River Resort
10.0 out of 10, Exceptional, (1)
"Beautiful and quiet property! A family member got married at Gable Hill and the property was so close to the venue. Rooms were comfortable, plenty of linens and towels. We all enjoyed our stay."
Rocky River Resort
Fridge, microwave, stovetop, coffee/tea maker
Rome City Waterfront Oasis w/ Beach & Dock!
9.8 out of 10, Exceptional, (16)
"We really enjoyed our stay. The lake was perfect. Will have to return when it’s warm enjoy more."
Rome City Waterfront Oasis w/ Beach & Dock!
Smart TV
Davis Street Shipshewana
10.0 out of 10, Exceptional, (47)
"House was very clean. Perfect for the 4 of us. We walked to where we needed to go. Would definitely stay again"
The price is ￥17,269
￥32,177 total
includes taxes & fees
Jun 1 - Jun 2
Davis Street Shipshewana
Don't see what you're looking for?
See all available properties in Middlebury
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.

Other types of properties in Middlebury you may be interested in

Courtyard
Essenhaus Inn & Conference Center
3.5 star property
9.8 out of 10, Exceptional, (915)
"Lovely hotel, great breakfast. Staff friendly and helpful. Close to shops. "
The price is ￥24,961
￥27,956 total
includes taxes & fees
May 30 - May 31
Essenhaus Inn & Conference Center
Restaurant
Hampton Inn & Suites Middlebury
2.5 star property
8.6 out of 10, Excellent, (1003)
"The easy parking "
The price is ￥15,880
￥17,786 total
includes taxes & fees
Jun 23 - Jun 24
Hampton Inn & Suites Middlebury
Property grounds
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, (5)
"Loved sitting on the deck, watching the boats & fishermen, sun coming up & going down. Loved the rise & shine donut’s, close to the Shipshewana Flea Market, just an an all around excellent time"
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
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.

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?

Recently renovated country cottage, 2.5 miles from Shipshewana: This vacation home rental outside of Middlebury is located in the city center and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a private yard and a selection of games.

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?

While exploring the area, visit family-friendly sights like Deutsch Kase Haus, or get outside and enjoy nature at Wellfield Botanic Gardens. In the larger area, you’ll find Dutch Creek Farm Animal Park and Blue Gate Performing Arts Center.

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.

Recent reviews of Middlebury properties
Expedia verified reviews

Blue Gate Garden Inn

Blue Gate Garden Inn

5/5 Excellent
Wonderful
"We were very happy with our room and stay. Next time we will take advantage of some of the wonderful amenities. Beautiful patio area with water feature and pretty views of the surrounding farms. And breakfast was so good! That was unexpected."
A verified traveler stayed at Blue Gate Garden Inn
Posted 13 hours ago
Blue Gate Garden Inn