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/large-sunny-4-bedroom-home-sleeps-8-and-1-minute-to-five-fabulous-restaurants/HA-321697520" class="class="static-page-link"">Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants</a> <a href="/property/6-acre-luxurious-country-home-with-goddess-point-lookout/HA-3212887172" class="class="static-page-link"">6-Acre Luxurious Country Home with Goddess Point Lookout</a> <a href="/property/cozy-family-and-pet-friendly-3br-home/HA-3213759559" class="class="static-page-link"">Cozy family and pet friendly 3BR Home</a> <a href="/property/historic-litchfield-county-home/HA-3213602352" class="class="static-page-link"">Historic Litchfield County Home</a> <a href="/property/private-apartment-in-southbury-103/HA-3214387123" class="class="static-page-link"">Private Apartment in Southbury 103</a> <a href="/property/watertown-home-with-yard-1-mi-to-echo-lake-park/BC-12794297" class="class="static-page-link"">Watertown Home with Yard 1 Mi to Echo Lake Park!</a> <a href="/property/private-apartment-in-southbury-102/BC-12564420" class="class="static-page-link"">Private Apartment in Southbury 102</a> <a href="/property/southbury-charming-studio-retreat-on-beautiful-grounds-sleeps-4/HA-3214832366" class="class="static-page-link"">Southbury Charming Studio Retreat on Beautiful Grounds — Sleeps 4</a> <a href="/property/new-one-bedroom-apartment-centrally-located-in-southbury/HA-3214355843" class="class="static-page-link"">New One Bedroom Apartment Centrally Located in Southbury</a> <a href="/property/private-apartment-in-southbury-102/HA-3214122952" class="class="static-page-link"">Private Apartment in Southbury 102</a>

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

The average cost for a cottage rental in Middlebury is $349 per night. Villa Bay 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.

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 2025, the data from Villa Bay shows that there are Over 5 private swimming pools or cottages with indoor pools in the Middlebury area along with other great amenities.

Middlebury Cottage Rentals By Owner

From US $214

9.2 (42 Reviews)

Cottage

Guest Cottage on Country Estate

Air Conditioner
Parking
Pet Friendly

Middlebury Cottage Rentals & Holiday Homes

Find the best cottages in Middlebury - We found 5 exact matches

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