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Compare 169 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Nautical 5 Bedroom 5 Bathroom Home on Diamond Lake
Property grounds

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
Exterior

Davis Street Shipshewana

10.0 out of 10, Exceptional, (63)
"Comfortable "
The price is SAR 413
SAR 756 total
includes taxes & fees
24 Feb - 25 Feb
Davis Street Shipshewana
Charming farmhouse in peaceful countryside
Living area

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (139)
"From start to finish, this charming farmhouse was perfect. From the updated decor to the ample sleeping space to the wood burning stove, this place has it all. Clean, cozy, and comfortable. Dixie the dogs warm welcome and watchful eye was an added bonus. We definitely would recommend this house to family and friends! "
Charming farmhouse in peaceful countryside
Lakefront Syracuse Home w/ Deck & Private Dock!
Syracuse Vacation Rental | 4BR | 3.5BA | 3,684 Sq Ft | Stairs Required

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 SAR 506
SAR 735 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!
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 SAR 544
SAR 1,416 total
includes taxes & fees
27 Jan - 28 Jan
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Newly Remodeled Cabin Steps from Sylvan Lake
The sofa houses a pullout bed suitable for teens or children.

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
`Burning Pine Inn' Farm House in Amish country.
Curl up in front of the beautiful fireplace and read your favorite book.

`Burning Pine Inn' Farm House in Amish country.

10.0 out of 10, Exceptional, (16)
"We stayed here for Thanksgiving day with family and it was super clean and well stocked. We will definitely recommend this to others."
`Burning Pine Inn' Farm House in Amish country.
Waterfront Diamond Lake - Sandy beach
Living area

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
Destination lake, Million dollar house, million-dollar views
Street side

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
Beautiful Lake house with private sandy beach, hot tub, kayaks, 4 beds, 4 bath
Enjoy nightly sunsets from your deck/beach/or hot tub!

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

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!
3BD Modern Home: Fireplace/Grill/Fire Pit
Fully Stocked Kitchen – Equipped with everything you need to whip up a gourmet meal or prepare a quick and easy snack. From stainless steel appliances to essential cookware and utensils, this kitchen has you covered for every culinary adventure.

3BD Modern Home: Fireplace/Grill/Fire Pit

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 SAR 519
SAR 1,531 total
includes taxes & fees
25 Jan - 26 Jan
3BD Modern Home: Fireplace/Grill/Fire Pit
Klinger Lake Cove - Sleeps 16-24
Property grounds

Klinger Lake Cove - Sleeps 16-24

The price is SAR 2,037
SAR 3,521 total
includes taxes & fees
25 Jan - 26 Jan
Klinger Lake Cove - Sleeps 16-24
Lake Wawasee waterfront home overlooking Johnson's Bay. New Renovations for 2024
Our view of Johnson's Bay

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
Beautiful Private Setting !!!
Property grounds

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 1,654 total
includes taxes & fees
24 Feb - 25 Feb
Beautiful Private Setting !!!
Charming Dairy Farm Home in Indiana Amish Country
Shipshewana Vacation Rental | 3BR | 1BA | 1,300 Sq Ft | 3 Stairs Required

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
Cottages on Sand Lake - The Cozy Cottage
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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 437
SAR 944 total
includes taxes & fees
24 Feb - 25 Feb
Cottages on Sand Lake - The Cozy Cottage
Primitive Goshen Pine Lodge with Fireplace!
Goshen Vacation Rental | 4BR | 2.5BA | 2,533 Sq Ft | 3 Steps Required

Primitive Goshen Pine Lodge with Fireplace!

9.2 out of 10, Wonderful, (9)
"Great house and property! "
Primitive Goshen Pine Lodge with Fireplace!
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL
Game room

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

10.0 out of 10, Exceptional, (21)
"Wonderful Host! "
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL
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

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

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
Terrace/patio

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 1,172 total
includes taxes & fees
9 Feb - 10 Feb
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Welcome to your Home Away From Home! Beautiful backyard and hot tub! Can't you see yourself relaxing the evening away?

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (48)
"Loved the property. Perfect for our family of"older kids". The ping pong table and hot tub got plenty of use! "
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
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.