What are the top rated Cottage Rentals in Middlebury?

There are a lot of options in Middlebury. If you plan on staying in the Middlebury area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Middlebury: <a href="/property/charming-spacious-home-near-towncenter-amenities-resturants-trails-and-parks/HA-1217463624" class="class="static-page-link"">Charming, spacious home near towncenter amenities, resturants, trails and parks.</a> <a href="/property/hot-tub-amish-farm-country-pergola-deck/HA-1219511571" class="class="static-page-link"">| Hot Tub | Amish Farm Country | Pergola | Deck |</a> <a href="/property/hot-tub-beautiful-backyard-oasis-newly-renovated/HA-1219691098" class="class="static-page-link"">HOT TUB | Beautiful Backyard Oasis|Newly Renovated</a> <a href="/property/charming-1912-bungalow-in-middlebury-indiana/HA-3213053195" class="class="static-page-link"">Charming 1912 Bungalow in Middlebury Indiana</a> <a href="/property/lemon-hill-amish-guest-house-an-amish-themed-whole-house-experience/HA-3213903491" class="class="static-page-link"">Lemon Hill Amish Guest House. . . an Amish themed, whole house experience.</a> <a href="/property/rustic-roots-cabin-3bd-3ba-cozy-shipshewana-nd/HA-3213647995" class="class="static-page-link"">Rustic Roots Cabin 3bd/3ba Cozy/Shipshewana/ND</a> <a href="/property/burning-pine-inn-farm-house-in-amish-country/HA-3213301585" class="class="static-page-link"">`Burning Pine Inn&#39; Farm House in Amish country.</a> <a href="/property/the-back-porch-havennstay-in-amish-country-yet-close-to-notre-dame/HA-3213528273" class="class="static-page-link"">The Back Porch HavennStay in Amish Country yet close to Notre Dame</a> <a href="/property/spacious-rural-apt-w-outdoor-amenities-close-to-shipshewana-and-toll-road/HA-3212536656" class="class="static-page-link"">Spacious, rural apt w/outdoor amenities - close to Shipshewana and Toll Road</a> <a href="/property/charming-3-bedroom-house-located-on-main-street-in-downtown-middlebury/HA-3214676770" class="class="static-page-link"">Charming 3-bedroom house located on Main Street in Downtown Middlebury</a>

How much does it cost to rent a cottage in Middlebury?

The average cost for a cottage rental in Middlebury is $111 per night. Rentattahoe has a wide list of great cottages near Middlebury that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Middlebury that allow pets?

Yes, here are the top cottage rentals in Middlebury that allow you to bring your pet: Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury The Wellington Cottage Charming, spacious home near towncenter amenities, resturants, trails and parks. Lakin' It Easy Farm Country Amish Country Newly Renovated | Hot Tub | Amish Farm Country | Pergola | Deck | <a href="/all/usa/indiana/middlebury" class="class="static-page-link"">See all pet-friendly vacation rentals in Middlebury on Rentattahoe</a>

Do you have any rental cottages in Middlebury that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Middlebury to find one that works for you.

Are there quality cottages in Middlebury that have indoor swimming pools?

As of 2026, the data from Rentattahoe shows that there are Over 2 private swimming pools or cottages with indoor pools in the Middlebury area along with other great amenities.

Middlebury Cottage Rentals By Owner

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

From US $141

10.0 (41 Reviews)

Cottage

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

Air Conditioner
Parking
TV

Middlebury Cottage Rentals & Holiday Homes

Find the best cottages in Middlebury - We found 2 exact matches

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