Photo by Ann Sair

Search Vacation Homes in Middlebury

  • 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

Check prices for these dates

Compare 171 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Nautical 5 Bedroom 5 Bathroom Home on Diamond Lake

9.8 out of 10, Exceptional, (8)
"Nice beachfront home. Clean, well stocked with essentials, ideal for reunions. Bathroom locks not present/working and some loose cinder blocks in the backyard could cause safety hazard. Overall enjoyed stay. "
Nautical 5 Bedroom 5 Bathroom Home on Diamond Lake

Davis Street Shipshewana

10.0 out of 10, Exceptional, (66)
"A nice house in a quiet neighborhood "
The price is SAR 413
SAR 756 total
includes taxes & fees
24 Feb - 25 Feb
Davis Street Shipshewana

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (140)
"We enjoyed our stay here! It was clean and fire made it cozy. Would recommend this place if you need somewhere to stay in Nappanee. "
Charming farmhouse in peaceful countryside

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!

Recently renovated country cottage, 2.5 miles from Shipshewana

10.0 out of 10, Exceptional, (226)
"While we didn't spend much time in the home as we were in town for a business show, our time there was really comfortable. We had snow on our visit which was shoveled off and brushed around our vehicles as well. "
The price is SAR 506
SAR 739 total
includes taxes & fees
24 Feb - 25 Feb
Recently renovated country cottage, 2.5 miles from Shipshewana

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

10.0 out of 10, Exceptional, (24)
"The stay was just arpund the corber from our home but felt like a getaway!"
The price is SAR 521
SAR 1,390 total
includes taxes & fees
24 Feb - 25 Feb
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Klinger Lake Cove - Sleeps 16-24

The price is SAR 1,935
SAR 3,398 total
includes taxes & fees
24 Feb - 25 Feb
Klinger Lake Cove - Sleeps 16-24

`Burning Pine Inn' Farm House in Amish country.

10.0 out of 10, Exceptional, (18)
"Excellent home away from home! "
`Burning Pine Inn' Farm House in Amish country.

Beautiful Lake house with private sandy beach, hot tub, kayaks, 4 beds, 4 bath

2.0 star property
Beautiful Lake house with private sandy beach, hot tub, kayaks, 4 beds, 4 bath

Newly Remodeled Cabin Steps from Sylvan Lake

10.0 out of 10, Exceptional, (32)
"Perfect little lakehouse getaway. Visited for a weekend and enjoyed the lake and the local town. The host was great at helping with our questions. Would go back."
Newly Remodeled Cabin Steps from Sylvan Lake

3BD Modern Home: Close to Downtown Elkhart

10.0 out of 10, Exceptional, (3)
"We came for a college swim meet. 4 adults stayed at this place and had plenty of room (could have slept 2 more). The house seemed like it was newly renovated and was very clean. Vicki was an awesome host and was very quick to respond to our questions. This house was definitely one of the nicer homes in the neighborhood and was located just a mile or two from downtown. Would recommend for anyone who needs to stay in Elkhart. "
3BD Modern Home: Close to Downtown Elkhart

Come enjoy this absolute dream for a family vacation or a getaway with friends!

9.8 out of 10, Exceptional, (6)
"Derek was a great host and the property was just as described, appreciated the Christmas 🎄 "
Come enjoy this absolute dream for a family vacation or a getaway with friends!

Destination lake, Million dollar house, million-dollar views

10.0 out of 10, Exceptional, (7)
"We had a couple small families from all over the US and we all had so much fun! Plenty of room for he kiddos and the place had a lot to offer! Will definitely come back again! "
Destination lake, Million dollar house, million-dollar views

Sleeps 18 w/ Indoor Basketball Pickleball Court, Heated Pool & Hot Tub!

9.2 out of 10, Wonderful, (16)
"Wonderful stay. Pool was fun for all. Gym with basketball hoop and pickleball court was an additional plus for this rental. All ages of our family loved it. I would highly rent this property again. "
Sleeps 18 w/ Indoor Basketball Pickleball Court, Heated Pool & Hot Tub!

Cozy Home Retreat

2.0 star property
10.0 out of 10, Exceptional, (7)
"This property is absolutely a gorgeous house. The decorations are tasteful and beautiful. It was without a doubt the best place we have stayed in. "
The price is SAR 563
SAR 1,289 total
includes taxes & fees
24 Feb - 25 Feb
Cozy Home Retreat

Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,

10.0 out of 10, Exceptional, (18)
"Songbird Haven was a perfect place for me and a couple business partners to stay at while in town for a convention at the MEC."
The price is SAR 484
SAR 1,025 total
includes taxes & fees
26 Feb - 27 Feb
Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,

Cottages on Sand Lake - The Cozy Cottage

9.2 out of 10, Wonderful, (18)
"It worked fine for us for a very winter getaway and is close to Shipshawana which is what I wanted. It is cosy so if you are looking for something spacious not the place. "
The price is SAR 378
SAR 869 total
includes taxes & fees
21 Mar - 22 Mar
Cottages on Sand Lake - The Cozy Cottage

Lake Wawasee waterfront home overlooking Johnson's Bay. New Renovations for 2024

9.4 out of 10, Exceptional, (41)
"Everything was very nice and clean. Owner was communicative and very helpful. No negatives as far as I am concerned. "
Lake Wawasee waterfront home overlooking Johnson's Bay. New Renovations for 2024

Charming Dairy Farm Home in Indiana Amish Country

9.8 out of 10, Exceptional, (36)
"We absolutely LOVED our stay at the Farmyard Inn!! The perfect, quiet and quaint place for our family’s annual “reset & unplug” trip. Everything was just as described in the listing. Truly a 10/10. We cannot wait to stay at the Farmyard Inn again! "
Charming Dairy Farm Home in Indiana Amish Country

Beautiful Private Setting !!!

9.8 out of 10, Exceptional, (15)
"The house was exactly as described. It was very well stocked with all our needs. A beautiful location. Our relatives visited daily and it accommodated us well. "
The price is SAR 896
SAR 1,641 total
includes taxes & fees
24 Feb - 25 Feb
Beautiful Private Setting !!!
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 property types in Middlebury

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

2.0 star property
9.8 out of 10, Exceptional, (7)
"Mike was a great host "
The price is SAR 413
SAR 522 total
includes taxes & fees
10 Mar - 11 Mar
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

The Wellington Cottage

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is SAR 338
SAR 525 total
includes taxes & fees
2 Mar - 3 Mar
The Wellington Cottage

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 SAR 469
SAR 1,164 total
includes taxes & fees
9 Mar - 10 Mar
The Back Porch Haven Stay in Amish Country yet close to 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.