1. USA
  2. Maryland
  3. Annapolis
  4. Cottage Rentals

Annapolis Cottage Rentals & Holiday Homes

Find the best cottages in Annapolis - We found 36 exact matches

About Annapolis Cottage Rentals on Rent By Owner

Searching for cottages to rent near Annapolis? Rent By Owner features more than 36 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 Annapolis 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. RBO’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Annapolis.

Are you planning to travel to the lakeside, beach, or mountain area? RBO’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.

Rent By Owner boasts of 36 holiday cottages and places to stay in Annapolis. The site provides unique Airbnb, VRBO, RBO-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.

Show more
Show less

Annapolis Cottage Rentals Frequently Asked Questions

The average cost for a cottage rental in Annapolis is $495 per night. RBO has a wide list of great cottages near Annapolis 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 Annapolis that allow you to bring your pet:

See all pet-friendly vacation rentals in Annapolis on Rent By Owner

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Annapolis to find one that works for you.
As of 2025, the data from Rent By Owner shows that there are Over 36 private swimming pools or cottages with indoor pools in the Annapolis area along with other great amenities.
About 36 cottages in Annapolis boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Annapolis on Rent By Owner