Photo by Ann Sair

Holiday Homes in Middlebury

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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Featured Holiday Homes in Middlebury

Nautical 5 Bedroom 5 Bathroom Home on Diamond Lake
Fridge, oven, stovetop, dishwasher

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
Smart TV

Davis Street Shipshewana

10.0 out of 10, Exceptional, (65)
"The house was well furnished and comfortable. It was quiet and peaceful. "
The price is AU$321
includes taxes & fees
17 Feb - 18 Feb
Davis Street Shipshewana
Charming farmhouse in peaceful countryside
Property grounds

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!
Fridge, microwave, stovetop, dishwasher

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
Exterior

Recently renovated country cottage, 2.5 miles from Shipshewana

10.0 out of 10, Exceptional, (226)
"We appreciate staying at this rental as it is always clean. The house is well stocked and the host is thoughtful in providing “little extras” for the stay. We will return."
The price is AU$314
includes taxes & fees
17 Feb - 18 Feb
Recently renovated country cottage, 2.5 miles from Shipshewana
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Outdoor pool

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

10.0 out of 10, Exceptional, (23)
"This house had everything my family and I needed to ring in the new year. We loved the clean, cozy feel of the house. Between the hot tub with outside TV and the game room, we had everything we needed to relax and enjoy the best family time without leaving the house. everything we needed, reason for us to "
The price is AU$590
includes taxes & fees
17 Feb - 18 Feb
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Klinger Lake Cove - Sleeps 16-24
Outdoor dining

Klinger Lake Cove - Sleeps 16-24

The price is AU$1,443
includes taxes & fees
18 Feb - 19 Feb
Klinger Lake Cove - Sleeps 16-24
`Burning Pine Inn' Farm House in Amish country.
Interior

`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
Outdoor dining

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
Waterfront Diamond Lake - Sandy beach
Pool

Waterfront Diamond Lake - Sandy beach

10.0 out of 10, Exceptional, (49)
"This house is great. We came with 7 adults and 3 kids for a week. The place is fully stocked with anything you need. The beach was the favorite playground for the kids. The house has all sorts of toys for kids and adults. These owners are really thoughtful. By night we had a fire in the fire pit and dinner outside. It was great. The house isn’t in the big lake, it’s on a sort of cove or pond which is quiet. The only problem….and it’s a big one….they came by unannounced and sprayed the lake for...
Waterfront Diamond Lake - Sandy beach
Newly Remodeled Cabin Steps from Sylvan Lake
Lake

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
Smart TV, fireplace, offices

3BD Modern Home: Close to Downtown Elkhart

10.0 out of 10, Exceptional, (3)
"My husband and I had to stay in Elkart, Indiana longer than expected, due to a mechanical breakdown. This rental was a great find and accommodating."
The price is AU$635
includes taxes & fees
18 Feb - 19 Feb
3BD Modern Home: Close to Downtown Elkhart
Come enjoy this absolute dream for a family vacation or a getaway with friends!
Terrace/patio

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
Fridge, microwave, oven, stovetop

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!
Blender, cookware/dishes/utensils, paper towels, dining tables

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
Terrace/patio

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 AU$547
includes taxes & fees
19 Feb - 20 Feb
Cozy Home Retreat
Songbird Haven, 3 min from town, full house, 3 bedrooms, 5 bed, 2 bathrooms,
Property grounds

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 AU$435
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
Property grounds

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 AU$399
includes taxes & fees
17 Feb - 18 Feb
Cottages on Sand Lake - The Cozy Cottage
Lake Wawasee waterfront home overlooking Johnson's Bay. New Renovations for 2024
Beach

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
Fridge, microwave, stovetop, coffee/tea maker

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
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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Other property types in Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Fridge, microwave, oven, stovetop

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

2.0 star property
9.8 out of 10, Exceptional, (7)
"The property was very clean. Cottage was in excellent shape. The property owner was VERY nice and quick on replying. It was out in the country but close to Middlebury and Shipshewana. Definitely will stay again when we come back up."
The price is AU$222
includes taxes & fees
10 Mar - 11 Mar
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
Outdoor dining

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

10.0 out of 10, Exceptional, (9)
"Cabin on Stone Lake had a spectacular view. Was clean and stocked with everything needed for a comfortable stay. We had tickets for NOTRE DAME football. This cabin was only 30 min away, an easy drive. Hope to return in the summer to enjoy the lake."
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
Smart TV, books

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
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.