Photo by Ann Sair

Middlebury Holiday 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
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Middlebury

The Back Porch Haven Stay in Amish Country yet close to Notre Dame
10.0 out of 10, Exceptional, (14)
"Very convenient location, close to the toll road. Very clean house, beautiful country setting. We would recommend this to anyone."
The price is AU$494
includes taxes & fees
3 Dec - 4 Dec
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
10.0 out of 10, Exceptional, (45)
"The house was beautiful! Very comfortable and welcoming. Will definitely stay here again if in the area!"
The price is AU$548
includes taxes & fees
20 Dec - 21 Dec
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, (8)
"So many stairs. Haha, it was good though. Kayaks and paddle boat were fun exercise as well. Relaxing on the top deck with the amazing view was exactly what I needed. "
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (132)
"3rd time staying at the same house. It’s been great every time!"
Charming farmhouse in peaceful countryside
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
10.0 out of 10, Exceptional, (107)
"Our stay was very relaxing! The cabin was cozy for the two of us. We loved the jacuzzi! "
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
Lakefront Syracuse Home w/ Deck & Private Dock!
9.8 out of 10, Exceptional, (8)
"In town for a wedding and it was the perfect location. "
Lakefront Syracuse Home w/ Deck & Private Dock!
Cozy ‘Haven of Rest’ Home w/ Amish Country Views!
10.0 out of 10, Exceptional, (49)
"What an awesome experience we had! Loved the stay and would highly recommend!! Jackie was so nice and made sure we had everything we needed!!😊"
Cozy ‘Haven of Rest’ Home w/ Amish Country Views!
Recently renovated country cottage, 2.5 miles from Shipshewana
10.0 out of 10, Exceptional, (223)
"It was a lovely cottage and a great location close to Blue Gate Theatre, Shipshewana and Middlebury. Very clean and comfortable. "
The price is AU$310
includes taxes & fees
24 Nov - 25 Nov
Recently renovated country cottage, 2.5 miles from Shipshewana
Relax by the lake- enjoy wine country and ski slopes
9.0 out of 10, Wonderful, (9)
"This Host! When my head was spinning from the tragic loss of my Father—she was direct and kind! Completely understanding of the needs of our family! This Is a beautiful property; fully stocked well taken care of and very clean! I can’t thank you enough, France, for making our stay as low stress possible! 💯% recommend checking this place out💕"
The price is AU$1,277
includes taxes & fees
24 Nov - 25 Nov
Relax by the lake- enjoy wine country and ski slopes
Live & Love Life on the Lake!
9.6 out of 10, Exceptional, (36)
"Very peaceful little home with a wonderful view of the lake. "
The price is AU$381
includes taxes & fees
23 Nov - 24 Nov
Live & Love Life on the Lake!
Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi
10.0 out of 10, Exceptional, (81)
"It was hard to tear myself away. Absolutely wonderful. Perfect for a couple!"
The price is AU$353
includes taxes & fees
3 Dec - 4 Dec
Serene Lake/Fishing Retreat w/outdoor hot tub and indoor Jaccuzzi
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
9.6 out of 10, Exceptional, (20)
"Great place. We had an amazing weekend and would use this house again! "
Waterfront home with dock, pool and hot tub! NOTRE DAME FOOTBALL
Rest & Relaxation
10.0 out of 10, Exceptional, (12)
"We were able to enjoy a few days in a serene environment. The cabin was cozy and comfortable and our hosts were friendly and responsive. The hosts were actually one of the highlights of the stay! "
Rest & Relaxation
Indian Lakes Cabin with private beach and dock lake side
9.6 out of 10, Exceptional, (74)
"Rustic cabin located on a beautiful lake. We had a great time with no issues. "
Indian Lakes Cabin with private beach and dock lake side
Vacation at Garver Lake ~ Private Beach For Your Enjoyment!
8.2 out of 10, Very good, (64)
"We rented this property for the weekend to have a little getaway for our family. There was only seven of us so it was perfect our sister mostly uses of wheelchair so it a pleasant surprise when we seen the wheelchair ramp going up to the back deck we all enjoyed ourselves and made some great memories with her. Everyone on and around the lake was friendly. We love the little beach area attached to the property and the fire pit it just has a really nice cabin feel, even though it’s a house....
Vacation at Garver Lake ~ Private Beach For Your Enjoyment!
Lake cottage with a great view 20 minutes from Shipshewana.
10.0 out of 10, Exceptional, (88)
"The communication was great. The house was very clean. Deck has great view of the lake. The flower gardens around the house added special touch. Hope to stay there again in warm weather."
Lake cottage with a great view 20 minutes from Shipshewana.
Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP
8.8 out of 10, Excellent, (19)
"Very clean spacious Great Lake house. Would stay here again. "
The price is AU$990
includes taxes & fees
24 Nov - 25 Nov
Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP
Beautiful Private Setting !!!
10.0 out of 10, Exceptional, (13)
"Our stay was fantastic! Host was awesome, house was clean and full of everything we needed. Even had a foot massager! Will be back "
The price is AU$692
includes taxes & fees
3 Dec - 4 Dec
Beautiful Private Setting !!!
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
9.4 out of 10, Exceptional, (23)
"Great cottage, outside of city life. Absolutely adorable dog on property to greet you coming and going. Nice set-up, everything we needed. GPS takes you past the cottage to another farm nearby; be careful if traveling in the dark. "
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
Cottages on Sand Lake - The Cozy Cottage
9.0 out of 10, Wonderful, (15)
"A comfortable retreat from the city life and if you are needing a little R&R, this is the place to be. The owners were very friendly and so helpful with any questions we had. The lake view was breathtaking. Forgot there was no dishwasher but turned out we did ok without it. Went to a sunflower patch at a nearby farm, enjoyed the kiddy size ice cream at the store. Not to mention all the fresh meats you could use for the grilling and than there was the ice cream. Wow you have to get some when...
The price is AU$344
includes taxes & fees
27 Nov - 28 Nov
Cottages on Sand Lake - The Cozy Cottage
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.
Don't see what you're looking for?
See all available properties in Middlebury
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Middlebury you may be interested in

Hampton Inn & Suites Middlebury
2.5 star property
8.4 out of 10, Very good, (1001)
"The hotel was comfortable and clean. Staff was very friendly & helpful. Would recommend…"
The price is AU$160
includes taxes & fees
24 Nov - 25 Nov
Hampton Inn & Suites Middlebury
Essenhaus Inn & Conference Center
3.5 star property
9.8 out of 10, Exceptional, (1001)
"Essenhaus was a great spot to return to after a day of shopping in Goshen to rest up for a day if shopping in Nappanee. It was quiet, had nice shops, a modern roomy bathroom and was very comfortable. The maple frosted filled pastry on the breakfast bar was superb! "
The price is AU$205
includes taxes & fees
1 Dec - 2 Dec
Essenhaus Inn & Conference Center
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
10.0 out of 10, Exceptional, (8)
"So many stairs. Haha, it was good though. Kayaks and paddle boat were fun exercise as well. Relaxing on the top deck with the amazing view was exactly what I needed. "
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Recently renovated country cottage, 2.5 miles from Shipshewana: This holiday home rental outside of Middlebury is located in the city centre, 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 garden and a selection of games.

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?

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

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.