Middlebury Vacation Homes

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A log cabin with red shutters and a small porch.

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Our top choices for Middlebury holiday homes

A hot tub on a wooden deck with a chair and a blanket.

A modern kitchen with white cabinets, a granite countertop, stainless steel appliances, and a bar stool.

A modern kitchen with a built-in TV, a dining area with a wooden table, and a living room with a black leather sofa.

A single-story house with a brick foundation and green siding, a front garage, and a well-maintained lawn.

1. HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

Middlebury

10.0 out of 10, Exceptional, (77 reviews)

10/10

Exceptional

(77 reviews)

"This is a great Property!"

Patrick B.

The price is HK$1,212

HK$1,212

HK$2,416 total

includes taxes & fees

8 Oct - 9 Oct

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

A hot tub with a view of a grassy field and a cloudy sky.

A modern living room with two black leather sofas, a wooden coffee table, a patterned rug, and a small side table with a lamp.

A modern kitchen with a built-in dishwasher, stainless steel refrigerator, and a dining area with a table and chairs.

A living room with a ceiling fan, a flat-screen TV, a sofa, a coffee table, and a window with curtains.

2. | Hot Tub | Amish Farm Country | Pergola | Deck |

Middlebury

10.0 out of 10, Exceptional, (103 reviews)

10/10

Exceptional

(103 reviews)

"This was a warm and cozy stay! "

Tim B.

The price is HK$817

HK$817

HK$2,050 total

includes taxes & fees

6 Oct - 7 Oct

A kitchen with a double sink, light-colored cabinets, and a refrigerator.

A modern kitchen with a stainless steel refrigerator, wooden cabinets, and a dining area with a round table and four chairs.

A room with a dark wooden dresser, a mirror, a vase with pink flowers, a lamp, and a sign that says "2 to 5 thanks to the Lord".

A single-story house with a stone foundation, a front porch, and a garage.

3. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated

2.0 star property

Middlebury

The price is HK$958

HK$958

HK$2,263 total

includes taxes & fees

6 Oct - 7 Oct

Farm Country Amish Country Newly Renovated

A spacious living room with a high ceiling, exposed wooden beams, a brick wall, a staircase, and a large television.

A bedroom with a large bed, wooden walls, and a skylight.

A wooden cabin with a porch, surrounded by autumn foliage and a small garden area.

A spacious living room with a sectional sofa, wooden beams, and a large sliding glass door leading to a balcony with a view of trees.

4. The Back Porch Haven Stay in Amish Country yet close to Notre Dame

The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Middlebury

10.0 out of 10, Exceptional, (34 reviews)

10/10

Exceptional

(34 reviews)

"Loved the house. Clean and comfortable and convenient to shipshewana and goshen."

Dianna D.

The price is HK$1,098

HK$1,098

HK$2,670 total

includes taxes & fees

26 Oct - 27 Oct

The Back Porch Haven Stay in Amish Country yet close to Notre Dame

A kitchen with light green cabinets, a white island with stools, a stainless steel refrigerator, and a 'Coffee' sign on the wall.

A bedroom with a bed, a chair, a door, and a window with a view.

A living room with two sofas, a coffee table, and a lamp. There is a kitchen visible in the background.

A dining area with a round wooden table surrounded by six wooden chairs, a woven placemat, and a framed picture on the wall.

5. | Amish Country Getaway | Farm Views | Fire Pit |

| Amish Country Getaway | Farm Views | Fire Pit |

Middlebury

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Great location! Close to Shipshewana and shopping and restaurants. Extremely clean, roomy, and had everything you need for a great stay."

Tamara B.

The price is HK$789

HK$789

HK$1,888 total

includes taxes & fees

5 Oct - 6 Oct

| Amish Country Getaway | Farm Views | Fire Pit |

A living room with a fireplace, a television, and a ceiling fan.

A wooden dresser with a mirror, a remote control, a tissue box, and a vase with dried plants.

6. Amish Country Getaway Farm Views Fire Pit

Amish Country Getaway Farm Views Fire Pit

2.0 star property

Middlebury

The price is HK$926

HK$926

HK$2,080 total

includes taxes & fees

5 Oct - 6 Oct

Amish Country Getaway Farm Views Fire Pit

A log cabin interior with a dining area, a living room, a staircase, and a coffee bar.

A cozy cabin interior with a wooden log wall, a window with sheer curtains, a coffee bar with various beverages and equipment, and a rustic aesthetic.

A wooden deck with a railing, benches, and a lantern.

A log cabin interior with two leather sofas, a wooden dining table, and a fireplace.

7. Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family

2.0 star property

Middlebury

The price is HK$3,541

HK$3,541

HK$5,126 total

includes taxes & fees

16 Oct - 17 Oct

Hidden Log Cabin Hot Tub Ping Pong Family

A cozy room with wicker chairs, a rocking chair, a teal rug, and a sign reading "Welcome to our Lake House."

A modern living room with a grey sofa set, a small side table, a patterned rug, and a window with a view of a lake.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a large island with stools, and a window with blinds.

A single-story house with a green roof and beige siding, a gravel driveway, and a mailbox with the number 7195.

8. Lake Front Cottage | Kayaks | Game Table Fun

Lake Front Cottage | Kayaks | Game Table Fun

Shipshewana

9.2 out of 10, Wonderful, (10 reviews)

9.2/10

Wonderful

(10 reviews)

"Lake Front Cottage was perfect for our weekend stay in LaGrange County. The host was responsive in communication and provided everything we needed for a pleasant stay."

Andrea S.

Lake Front Cottage | Kayaks | Game Table Fun

A modern building with a sloped roof, a wooden porch, and a small outdoor seating area.

A compact kitchen with a central island, a dining area with a bench, and a small sleeping area with a bed.

A kitchen with white cabinetry, a marble countertop, a black microwave, and a potted plant.

A modern kitchen with a white countertop, two black bar stools, a clock, and a window.

9. Hearthstone Hideaway #5 | Shewana Tiny Home Village

Hearthstone Hideaway #5 | Shewana Tiny Home Village

Shipshewana

9.6 out of 10, Exceptional, (7 reviews)

9.6/10

Exceptional

(7 reviews)

"We enjoyed staying at the tiny house. Was clean and quiet. Had about everything we needed for are two night stay. Will be back"

Joe R.

The price is HK$725

HK$725

HK$1,673 total

includes taxes & fees

7 Oct - 8 Oct

Hearthstone Hideaway #5 | Shewana Tiny Home Village

A house with a porch, a window with a flower box, and a chair outside.

A wooden dining table with two cushioned benches and a potted plant on top.

A garden with a small waterfall, rocks, and various plants.

A residential house with a gray exterior, white window frames, and a small porch area.

10. Millie's Cottage

Millie's Cottage

Shipshewana

10.0 out of 10, Exceptional, (324 reviews)

10/10

Exceptional

(324 reviews)

"Great property. Good location. Would stay again."

BigJohnsCards24

The price is HK$1,130

HK$1,130

HK$1,642 total

includes taxes & fees

4 Oct - 5 Oct

Millie's Cottage

A spacious living room with a wooden dining table, chairs, a television, and a large window with curtains.

A walk-in closet with multiple shelves, a hanging rod, and a door with a light switch.

A deck with a round table and chairs, a red umbrella, and a view of a lake.

A bedroom with a bed, a nightstand, a dresser, a chair, a ceiling fan, and a door leading to another room.

11. Lake House Shallow Sandy Kayaks Family Fun

Lake House Shallow Sandy Kayaks Family Fun

2.0 star property

Shipshewana

The price is HK$1,292

HK$1,292

HK$3,083 total

includes taxes & fees

6 Oct - 7 Oct

Lake House Shallow Sandy Kayaks Family Fun

A lakeside seating area with Adirondack chairs and a canoe, surrounded by a grassy area and a large tree.

A spacious living area with a dining table, chairs, a TV, and a large window with curtains.

A bedroom with two beds, a bench, a nightstand, a ceiling fan, and a window with curtains.

A modern kitchen with white cabinets, a gas stove, a microwave, and a refrigerator.

12. Lake House | Shallow Sandy | Kayaks | Family Fun

Lake House | Shallow Sandy | Kayaks | Family Fun

Middlebury

9.8 out of 10, Exceptional, (11 reviews)

9.8/10

Exceptional

(11 reviews)

"Great house for a friends getaway. The house is fully equipped to enjoy meals, relax and enjoy the lake. Loved the coffee set up and small extras for guest to enjoy."

Angela D.

The price is HK$1,184

HK$1,184

HK$2,713 total

includes taxes & fees

6 Oct - 7 Oct

Lake House | Shallow Sandy | Kayaks | Family Fun

A covered porch with two chairs and a table, a brick wall, and string lights.

A two-story house with a covered porch, a brick chimney, and a gravel driveway leading to the front door.

A bedroom with a wooden bed, a nightstand with a plant, a clock, and a door.

A compact kitchen with a stove, sink, and dishwasher, featuring white cabinets and a clock on the wall.

13. Superb 5-bedroom farmhouse in Goshen with WiFi, AC

Superb 5-bedroom farmhouse in Goshen with WiFi, AC

Goshen

9.8 out of 10, Exceptional, (53 reviews)

9.8/10

Exceptional

(53 reviews)

"We had a great stay!!"

Sally F.

The price is HK$1,875

HK$1,875

HK$2,275 total

includes taxes & fees

1 Nov - 2 Nov

Superb 5-bedroom farmhouse in Goshen with WiFi, AC

A small, single-story house with a dark roof, a front porch with two chairs, and a pathway leading to the entrance.

A modern two-story house with a dark exterior, large windows, and a front porch with a wooden chair.

A bedroom with a loft bed, a small table, and a door leading to a balcony.

A bathroom with a white sink, two bottles of soap, a wooden ring, and a towel.

14. Natural Nook | Tiny Home #2 in Amish Country!

Natural Nook | Tiny Home #2 in Amish Country!

Shipshewana

9.8 out of 10, Exceptional, (22 reviews)

9.8/10

Exceptional

(22 reviews)

"It was quite and peaceful… beautiful setting… loved the tiny house"

Carla

The price is HK$725

HK$725

HK$1,907 total

includes taxes & fees

5 Oct - 6 Oct

Natural Nook | Tiny Home #2 in Amish Country!

A spacious loft with a stone fireplace, large windows, and a cozy seating area.

A wooden deck with wicker furniture overlooking a body of water and autumn foliage.

A modern kitchen with a brick island, stainless steel appliances, and a view to the outside.

A kitchen with a brick island, stainless steel appliances, and a hanging light fixture.

15. Riverhaven! Glamorous A-Frame on St Joe River!

Riverhaven! Glamorous A-Frame on St Joe River!

Bristol

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Beautiful place to stay! The home was very clean and the location was perfect!"

Emmajo R.

Riverhaven! Glamorous A-Frame on St Joe River!

A kitchenette with a coffee maker, a mug, a bowl, and a shelf with coffee containers.

A single-story house with a metal roof, a front porch, and a welcome sign.

A garden with a large tree, a birdhouse, and a trash bin.

A living room with a leather sofa, a coffee table, and a view of the garden through a window.

16. Songbird Haven, 3 min from town, Pumpkinvine, MEC,concerts. 3 bedroom, 2 bath.

Songbird Haven, 3 min from town, Pumpkinvine, MEC,concerts. 3 bedroom, 2 bath.

Shipshewana

9.6 out of 10, Exceptional, (45 reviews)

9.6/10

Exceptional

(45 reviews)

"I would highly recommend this place to anyone, we will book it for our next trip back to Shipshewana. It is a very quiet location, the beds are super comfy and there is plenty of space."

Maria

The price is HK$1,844

HK$1,844

HK$3,411 total

includes taxes & fees

5 Oct - 6 Oct

Songbird Haven, 3 min from town, Pumpkinvine, MEC,concerts. 3 bedroom, 2 bath.

A two-story building with a wooden facade and a metal roof, featuring a porch with chairs and a small garden area.

A dining area with a wooden table and chairs, a wall clock, and a window.

A neatly made bed with a white and beige blanket, a bedside table with two glasses of orange drink, and a small stool.

A kitchen with dark green cabinets, a stainless steel refrigerator, a double sink, and a microwave.

17. Serene Sanctuary | Tiny Home #1 in Amish Country!

Serene Sanctuary | Tiny Home #1 in Amish Country!

Shipshewana

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Wonderful time!"

Julie G.

The price is HK$725

HK$725

HK$1,908 total

includes taxes & fees

13 Oct - 14 Oct

Serene Sanctuary | Tiny Home #1 in Amish Country!

A modern kitchen with a marble countertop, a built-in oven, and a ceiling fan.

A modern house with a dark exterior, a large front door, and a covered patio area with two wooden chairs and a small table.

A kitchen with a central island, two bar stools, and a world map on the wall.

A small wooden cabin with a black door, two windows, and a porch with two chairs.

18. Whispering Cottage #3 | Shewana Tiny Home Village

Whispering Cottage #3 | Shewana Tiny Home Village

Shipshewana

8.8 out of 10, Excellent, (8 reviews)

8.8/10

Excellent

(8 reviews)

"Very awesome place. A bit overpriced but still a good deal and experience."

Edward D.

The price is HK$725

HK$725

HK$1,655 total

includes taxes & fees

4 Oct - 5 Oct

Whispering Cottage #3 | Shewana Tiny Home Village

The bedroom has a queen sized bed, electric fireplace, and TV for cozy, restful evenings

A small, single-story building with a dark roof and wooden siding, featuring a front porch with two chairs and a small table.

A hallway with a wooden floor, a dining table with chairs, a black refrigerator, and a door leading to another room.

A small, single-story wooden house with a dark door and two windows, a covered porch with chairs, and a paved pathway leading to the entrance.

19. Simple Serenity Loft | Tiny Home #6 in Amish Country!

Simple Serenity Loft | Tiny Home #6 in Amish Country!

Shipshewana

9.4 out of 10, Exceptional, (6 reviews)

9.4/10

Exceptional

(6 reviews)

"This place was amazing! The animals in the back were a bonus. The only thing we could think to make it better was a full length mirror. Would recommend to all our family and friends to stay here!"

Cindy T.

The price is HK$725

HK$725

HK$1,908 total

includes taxes & fees

5 Oct - 6 Oct

Simple Serenity Loft | Tiny Home #6 in Amish Country!

A modern two-story house with a dark exterior, a wooden front porch, and a fenced yard.

A building with a metal roof and a tree in front. There are chairs and a table outside.

A patio area with two Adirondack chairs, a fire pit in the center, and a small table with chairs in the background.

A modern interior with a high ceiling, exposed beams, and a balcony with a metal railing.

20. Little Luxe Retreat #7 | Tiny Home + Fire Table

Little Luxe Retreat #7 | Tiny Home + Fire Table

Shipshewana

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Very enjoyable stay."

June P.

The price is HK$725

HK$725

HK$1,926 total

includes taxes & fees

7 Oct - 8 Oct

Little Luxe Retreat #7 | Tiny Home + Fire Table

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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Top Middlebury Hotel Reviews

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

10/10 Excellent

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

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