The 10 best holiday homes in Middlebury, USA | Booking.com
Skip to main content

Holiday Homes in Middlebury

Find the holiday homes that appeal to you the most

The best holiday homes in Middlebury

Check out our pick of great holiday homes in Middlebury

Show hotels on map

Filter by:

Review score

The Wellington Lake Cottage

Middlebury

Located in Middlebury in the Indiana region, The Wellington Lake Cottage features a patio and inner courtyard views. This property offers access to a balcony, free private parking and free WiFi.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 28 reviews
Price from
US$89.10
1 night, 2 adults
Check availability

Lakin' It Easy

Middlebury

Featuring air-conditioned accommodation with a balcony, Lakin' It Easy is set in Middlebury.

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 16 reviews
Price from
US$130.50
1 night, 2 adults
Check availability

Cozy Amish Country Cabin on Shipshewana Lake!

Shipshewana (Near Middlebury)

Featuring air-conditioned accommodation with a patio, Cozy Amish Country Cabin on Shipshewana Lake! is set in Shipshewana. This holiday home is 33 km from Midwest Museum of American Art.

Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 12 reviews
Check availability

Howe Retreat with Fire Pit and Private Boat Dock!

Howe (Near Middlebury)

Howe Retreat with Fire Pit and Private Boat Dock! is set in Howe. Free WiFi is available throughout the property and Midwest Museum of American Art is 43 km away.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 6 reviews
Check availability

Shipshewana Guest House with Fire Pit!

Shipshewana (Near Middlebury)

Shipshewana Guest House with Fire Pit! offers accommodation in Shipshewana, 35 km from Midwest Museum of American Art. The accommodation offers a 24-hour front desk and parking on-site.

Scored out of 10, guest rating 10.0
Exceptional - What previous guests thought, 21 reviews
Check availability

Cozy Haven of Rest Home with Amish Country Views!

Shipshewana (Near Middlebury)

Situated in Shipshewana in the Indiana region, Cozy Haven of Rest Home with Amish Country Views! features a patio. The property is non-smoking and is located 39 km from Midwest Museum of American Art....

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 16 reviews
Check availability
All holiday homes in Middlebury

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes in Middlebury and surroundings in the past month

See all

Research, refine and make plans for your whole trip

Hotels near South Bend Regional Airport

Got a stopover, late arrival or early departure? Find hotels conveniently close to the airport.

Hotels near Fort Wayne Airport

Perfect for a late arrival or early departure.

Hotels in Middlebury

More great accommodation options for your trip.

Hotels with Parking in Middlebury

More great accommodation options for your trip.

Holiday Homes in Elkhart

Find more hotels in a city close to Elkhart.

Holiday Homes in South Bend

Find more hotels in a city close to South Bend.

When to visit the United States

Events, prices, the weather – everything you need to know about the best time to visit the United States.

Holiday Homes in New York

Discover another destination in the United States.

Holiday Homes in Las Vegas

Discover another destination in the United States.