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-1760-cape-nestled-in-the-foothills-of-litchfield-county/HA-3211182588" class="class="static-page-link"">Charming 1760 Cape Nestled in the Foothills of Litchfield County</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/clean-bright-2-bedroom-cottage-shares-8-acres/HA-3213089784" class="class="static-page-link"">Clean &amp; Bright 2 Bedroom Cottage shares 8 Acres</a> <a href="/property/historic-litchfield-county-home/HA-3213602352" class="class="static-page-link"">Historic Litchfield County Home</a> <a href="/property/charming-1-bedroom-apartment-with-off-street-parking-in-middlebury/HA-3214497842" class="class="static-page-link"">Charming 1-bedroom apartment with off street parking in Middlebury.</a> <a href="/property/rustic-colonial-home-with-private-rooms/BC-10553797" class="class="static-page-link"">Rustic Colonial Home with Private Rooms</a> <a href="/property/courtyard-by-marriott-waterbury-downtown/EP-34227" class="class="static-page-link"">Courtyard by Marriott Waterbury Downtown</a> <a href="/property/heritage-hotel-golf-spa-conference-center/EP-35389" class="class="static-page-link"">Heritage Hotel, Golf, Spa &amp; Conference Center</a> <a href="/property/heritage-hotel-golf-spa-conference-center/BC-57791" class="class="static-page-link"">Heritage Hotel, Golf, Spa &amp; Conference Center</a>

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

The average cost for a cottage rental in Middlebury is $318 per night. Cruiseandresorts 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 2026, the data from Cruiseandresorts shows that there are Over 108 private swimming pools or cottages with indoor pools in the Middlebury area along with other great amenities.

Middlebury Cottage Rentals By Owner

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

From US $379

10.0 (51 Reviews)

House

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

Air Conditioner
Parking
Pet Friendly

Middlebury Cottage Rentals & Holiday Homes

Find the best cottages in Middlebury - We found 108 exact matches

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