Middlebury Cottage Rentals & Holiday Homes

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

Destination
Dates
Guests
Search
  • Up-front pricing
  • No markup
  • Trusted partners

Compare Cottage Rentals in Middlebury

2 Cottage Rentals
Sort by

People Visiting Middlebury Also Like

See More Places to Stay in Middlebury

About Middlebury Cottage Rentals on Casai.com

Searching for cottages to rent near Middlebury? Casai features more than 2 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Middlebury have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Casai’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Middlebury.

Are you planning to travel to the lakeside, beach, or mountain area? Casai’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Casai boasts of 2 holiday cottages and places to stay in Middlebury. The site provides unique Airbnb, VRBO, Casai-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

Cottage Rentals: Explore Top Destinations

Cottage Rentals in Adirondack Region
Cottage Rentals in Asheville
Cottage Rentals in Bass Lake
Cottage Rentals in Beavers Bend Resort Park
Big Bear Cottage Rentals
Big Sur Cottage Rentals
Blue Ridge Cottage Rentals
Boone Cottage Rentals
Branson Cottage Rentals
Broken Bow Cottage Rentals
Brown County Cottage Rentals
Bryson City Cottage Rentals
Buffalo National River Cottage Rentals
Cape Cod Cottage Rentals

Frequently Asked Questions About Middlebury Rental Cottages

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:

How much does it cost to rent a cottage in Middlebury?
The average cost for a cottage rental in Middlebury is $154 per night. Casai 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 Casai.com shows that there are Over 2 private swimming pools or cottages with indoor pools in the Middlebury area along with other great amenities.
Are there luxury cottages in Middlebury?
Yes, there are luxury cottages in Middlebury. Find more luxury, lakefront, winter, & last-minute cottage rentals near Middlebury.