1. USA
  2. Massachusetts
  3. Chatham
  4. Cottage Rentals

Chatham Cottage Rentals & Holiday Homes

Find the best cottages in Chatham - We found 38 exact matches

About Chatham Cottage Rentals on Winters Vacations Rentals

Searching for cottages to rent near Chatham? Winters Vacations Rentals features more than 38 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 Chatham 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. Winters Vacations Rentals’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Chatham.

Are you planning to travel to the lakeside, beach, or mountain area? Winters Vacations Rentals’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.

Winters Vacations Rentals boasts of 38 holiday cottages and places to stay in Chatham. The site provides unique Airbnb, VRBO, Winters Vacations Rentals-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.

Frequently Asked Questions About Chatham Cottage Rentals

What are the top rated Cottage Rentals in Chatham?

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

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

The average cost for a cottage rental in Chatham is $474 per night. Wintersvacationsrentals has a wide list of great cottages near Chatham that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

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

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

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

As of 2026, the data from Wintersvacationsrentals shows that there are Over 38 private swimming pools or cottages with indoor pools in the Chatham area along with other great amenities.