Anne Arundel County Cottage Rentals & Holiday Homes
Find the best cottages in Anne Arundel County - We found 94 exact matches
About Anne Arundel County Luxury Rental on Stay If You Dare
Searching for cottages to rent near Anne Arundel County? Stay If You Dare features more than 94 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 Anne Arundel County 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. Stay If You Dare’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Anne Arundel County.
Are you planning to travel to the lakeside, beach, or mountain area? Stay If You Dare’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.
Stay If You Dare boasts of 94 holiday cottages and places to stay in Anne Arundel County. The site provides unique Airbnb, VRBO, Stay If You Dare-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 Anne Arundel County Cottage Rentals
What are the top rated Cottage Rentals in Anne Arundel County?
There are a lot of options in Anne Arundel County. If you plan on staying in the Anne Arundel County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Anne Arundel County:
- Annapolis waterfront "tiny house" in garden setting
- Potomac River Getaway at McKays Beach
- Truly Waterfront Cottage
- Rare find! Chic cottage, salt water heated pool May 15-Oct15.
- Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
- Enchanting West River Retreat
- Windswept Getaway
- Turtle Cove at Cedar Cove Marina
- Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park
- Charming 2-bedroom cottage
How much does it cost to rent a cottage in Anne Arundel County?
The average cost for a cottage rental in Anne Arundel County is $331 per night. Stayifyoudare has a wide list of great cottages near Anne Arundel County that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Anne Arundel County that allow pets?
Yes, here are the top cottage rentals in Anne Arundel County that allow you to bring your pet:
- Cottage Located on the Patuxent River!
- Cottage Escape in the Allegany Mountains
- Sunny Glen Burnie Home - On-site Water Access
- Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
See all pet-friendly vacation rentals in Anne Arundel County on Stayifyoudare
Do you have any rental cottages in Anne Arundel County that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Anne Arundel County to find one that works for you.
Are there quality cottages in Anne Arundel County that have indoor swimming pools?
As of 2026, the data from Stayifyoudare shows that there are Over 94 private swimming pools or cottages with indoor pools in the Anne Arundel County area along with other great amenities.
