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Find Family Hotels in Middlebury, IN from CA $118

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Check prices for these dates

Tonight
Nov 10 - Nov 11
Tomorrow
Nov 11 - Nov 12
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Middlebury family-friendly hotels

A billiards room with a pool table, a seating area, and a window providing a view of the outdoors.

1. Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center
3.5 star property
Middlebury
9.6 out of 10, Exceptional, (1,010 reviews)
The price is CA $151
CA $169 total
includes taxes & fees
Nov 15 - Nov 16
Essenhaus Inn & Conference Center
A spacious hotel lobby with a central seating area, multiple dining tables, and a large sofa.

2. Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury
2.5 star property
Middlebury
8.2 out of 10, Very good, (1,000 reviews)
The price is CA $161
CA $180 total
includes taxes & fees
Nov 24 - Nov 25
Hampton Inn & Suites Middlebury
A room with a wooden sliding door, a rocking chair, and a kitchen area visible through an open door.

3. Lemon Hill Amish Guest House. . . an Amish themed, whole house experience.

Lemon Hill Amish Guest House. . . an Amish themed, whole house experience.
Middlebury
10.0 out of 10, Exceptional, (57 reviews)
The price is CA $177
CA $354 total
includes taxes & fees
Nov 24 - Nov 25
Lemon Hill Amish Guest House. . . an Amish themed, whole house experience.
A gravel path leading to a white house with a garage, surrounded by grassy fields and trees.

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

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Middlebury
10.0 out of 10, Exceptional, (77 reviews)
The price is CA $240
CA $276 total
includes taxes & fees
Nov 15 - Nov 16
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
A hot tub with a view of a grassy field and a cloudy sky.

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

| Hot Tub | Amish Farm Country | Pergola | Deck |
Middlebury
10.0 out of 10, Exceptional, (104 reviews)
The price is CA $176
CA $378 total
includes taxes & fees
Nov 23 - Nov 24
| Hot Tub | Amish Farm Country | Pergola | Deck |
A hotel room with two beds, a nightstand, a lamp, and a floral tapestry.

6. The Wellington Cottage

The Wellington Cottage
3.0 star property
Middlebury
10.0 out of 10, Exceptional, (13 reviews)
  • cleanliness
    Remodeled lakeside cottage offers games, kayaks, firepit, and toys for all ages, creating cherished memories.
The price is CA $128
CA $155 total
includes taxes & fees
Nov 16 - Nov 17
The Wellington Cottage
A kitchen with a double sink, light-colored cabinets, and a refrigerator.

7. Farm Country Amish Country Newly Renovated

Farm Country Amish Country Newly Renovated
2.0 star property
Middlebury
The price is CA $214
CA $432 total
includes taxes & fees
Nov 23 - Nov 24
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.

8. 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, (36 reviews)
The price is CA $208
CA $472 total
includes taxes & fees
Nov 11 - Nov 12
The Back Porch Haven Stay in Amish Country yet close to Notre Dame
A covered patio with brick flooring, green cushioned seating, and a stone planter.

9. Van Buren Hotel

Van Buren Hotel
4.0 star property
Shipshewana
9.2 out of 10, Wonderful, (1,594 reviews)
  • cleanliness
    Family-friendly escapes with a sparkling indoor pool that kids will love, plus fitness centre and premium entertainment options.
The price is CA $145
CA $167 total
includes taxes & fees
Nov 15 - Nov 16
Van Buren Hotel
A hotel room with two beds, each with a patterned bedspread, a nightstand with a lamp, and a framed cityscape picture on the wall.

10. Super 8 by Wyndham Shipshewana

Super 8 by Wyndham Shipshewana
2.0 star property
Shipshewana
8.8 out of 10, Excellent, (1,006 reviews)
The price is CA $119
CA $136 total
includes taxes & fees
Nov 28 - Nov 29
Super 8 by Wyndham Shipshewana
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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Choose what matters most at family-friendly hotels in Middlebury

Breakfast included
Pool

Top Middlebury Hotel Reviews

A billiards room with a pool table, a seating area, and a window providing a view of the outdoors.
Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center
Middlebury

10/10 Excellent

Tout était parfait très propre et la bouffe était très bonne
Canada
Marc
Reviewed November 5, 2026
Essenhaus Inn & Conference Center

Frequently Asked Questions

What's Middlebury like for family-friendly vacations?

The welcoming destination of Middlebury is a good choice if you've been considering a getaway with your kids. The biking trails, gardens, and hiking trails are just a few things that make this an attractive place for a family vacation. Fly into Goshen, IN (GSH-Goshen Municipal), which is located 11.5 mi (18.5 km) from the city center.

When’s the best time to book a family-friendly vacation in Middlebury?

The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Middlebury is 45 inches.

What's there to see and do with your family in Middlebury?

While you and your family are staying in Middlebury, you might want to visit some family-friendly attractions such as Middlebury Public Library, Deutsch Kase Haus, and Dutch Creek Farm Animal Park. Make sure you have lots of time for activities like Blue Gate Theater and Shipshewana Auction and Flea Market.

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