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

Next weekend
In two weeks
In one month
In two months

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (138)
"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! "
The price is HK$584
HK$1,041 total
includes taxes & fees
20 Jan - 21 Jan
Charming farmhouse in peaceful countryside

Davis Street Shipshewana

10.0 out of 10, Exceptional, (63)
"Comfortable "
The price is HK$856
HK$1,596 total
includes taxes & fees
29 Jan - 30 Jan
Davis Street Shipshewana

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)
"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 HK$1,051
HK$1,552 total
includes taxes & fees
29 Jan - 30 Jan
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, (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 HK$1,129
HK$2,939 total
includes taxes & fees
20 Jan - 21 Jan
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

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.

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.

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 bed, 4 bath

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

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!

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 !!!

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 HK$1,861
HK$3,449 total
includes taxes & fees
19 Jan - 20 Jan
Beautiful Private Setting !!!

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

Primitive Goshen Pine Lodge with Fireplace!

9.0 out of 10, Wonderful, (8)
"Everything was wonderful. Just as advertised, and better!!! Have only 3 comments to help it be even better: 1. Can opener in kitchen is not functional 2. Mattress in big bedroom (with bathroom) was very hard. My son and son-in-law swapped it for the floor mattress in the loft. 3. SAFETY ISSUE CONCERN: During my initial walk thru of the house, I nearly fell into the facility room after opening the door. Since all of the floor I had been walking on was level, I was not prepared for the step...
Primitive Goshen Pine Lodge with Fireplace!

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

Blue Birds Perch: Stunning Home on Private Hilltop

10.0 out of 10, Exceptional, (39)
"First, we were greeted with fresh donuts...um yes please! A basket withgranola bars and popcorn too.The house was warm, cozy, and had 3 decorated Christmas trees...the fire place was perfect to sit by.The host came and introduced himself.Each bathroom had cute soaps, the bedrooms were ama ing...we loved the enture atmosphere...we will definitely be back!"
Blue Birds Perch: Stunning Home on Private Hilltop

Tranquil lakeside retreat

10.0 out of 10, Exceptional, (10)
"We had a great week stay. Very clean house, nice appliances, nice view of lake, a lot of helpful items. Dog bowls, games, lake, a lot of plates/cups, trash bags. Makes you feel right at home!"
Tranquil lakeside retreat

Riverhaven! Gorgeous A-Frame On St Joe River!!

10.0 out of 10, Exceptional, (17)
"Property was very clean, spacious and had a beautiful view. We were impressed on how stocked it was with everything that was needed. It's perfect if you want to get away from the city. Would definitely come back."
The price is HK$1,861
HK$4,049 total
includes taxes & fees
19 Jan - 20 Jan
Riverhaven! Gorgeous A-Frame On St Joe River!!

Choo Choo Inn

10.0 out of 10, Exceptional, (16)
"We stayed at the Choo Choo Inn while visiting family over Christmas. It was a great spot to stay with our dog and had cute touches all around the rental. We will definitely stay here again when we’re visiting home. "
The price is HK$1,022
HK$1,178 total
includes taxes & fees
20 Jan - 21 Jan
Choo Choo Inn

Sturgis Home w/ Yard < 1 Mi to Minnewaukan Lake

10.0 out of 10, Exceptional, (11)
"We really enjoyed our stay. The home was kept up nicely and very clean. It was so nice to be able to park in the garage. The view to the private back yard was wonderful. There were several small comforts and conveniences that we enjoyed such as water bottles in the refrigerator, keurig coffee, and microwave popcorn. The only thing that we had any issue with was that the satellite dish TV was not very user friendly. We couldn't figure out how to watch what we wanted to. Fortunately, we were able...
Sturgis Home w/ Yard < 1 Mi to Minnewaukan Lake
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

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

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 HK$973
HK$2,399 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

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.