1. USA
  2. Indiana
  3. Madison
  4. Bennington
  5. Cottage Rentals

Bennington Cottage Rentals & Holiday Homes

Find the best cottages in Bennington - We found 37 exact matches

About Bennington Cottage Rentals on SunSkiResorts

Searching for cottages to rent near Bennington? SunSki features more than 37 cottages that are perfect for your next trip. Escape the snow and slopes and discover luxury cottage rentals just a few miles away from the lake or beach. These cottage rentals in Bennington offer hot baths, are kid-friendly & family-friendly, and are situated near top local attraction spots, ensuring guests have the best travel experience possible. SunSki’s cottage listings come in all shapes and sizes, catering to large groups, friends, or couples in Bennington.

Planning to travel to the lakeside, beach, or mountain area? SunSki’s cottage rentals offer a wide selection, providing direct access to the owners of these cottage rentals and offering you the best opportunity to find a good price.

SunSki boasts of 37 holiday cottages and places to stay in Bennington. The site provides unique Airbnb, VRBO, ski-style cottages to fit your trip or getaway with your friends and family. Whether it's a weekend getaway, spring break, summer vacation, or annual holiday, all fit within your budget.

Show more
Show less

Frequently Asked Questions About Bennington Rental Cottages

There are a lot of options in Bennington. If you plan on staying in the Bennington area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Bennington:

The average cost for a cottage rental in Bennington is $267 per night. SunSki has a wide list of great cottages near Bennington that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Bennington that allow you to bring your pet:

See all pet-friendly vacation rentals in Bennington on SunSkiResorts

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Bennington to find one that works for you.
As of 2025, the data from SunSkiResorts shows that there are Over 37 private swimming pools or cottages with indoor pools in the Bennington area along with other great amenities.
About 37 cottages in Bennington boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Bennington on SunSkiResorts
Yes, there are luxury cottages in Bennington. Find more luxury, lakefront, winter, & last-minute cottage rentals near Bennington.