Cottages in Annapolis

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

• Pet-Friendly Edgewater Cottage Big Fenced Yard
• Cozy Cottage w Beach Access Near Annapolis
• Private & Quiet Cottage in West Annapolis
• Cozy 1-bedroom cottage in adorable Annapolis on a private wooded area
• Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
• 2-bedroom waterfront Cottage in Annapolis, MD. Cove of Cork, view of the Severn.
• Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
• Walk to everything! Downtown Historic Annapolis “Arts District”
• Chesapeake Cottage
• Waterfront nature retreat, contemporary home w/pier by Annapolis. Pet Friendly!

The average cost for a cottage rental in Annapolis is $494 per night. Smartours 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:

• Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.
• Pet-Friendly Cottage Walk to USNA Stadium
• Your Annapolis Waterfront retreat for a weekend or any-day getaway! Great lodging for Plebe Parent's Weekend - and all your USNA activities.
• Weems Creek Cottage, Annapolis Waterfront

See all pet-friendly vacation rentals in Annapolis on Smartours

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 2026, the data from Smartours shows that there are Over 43 private swimming pools or cottages with indoor pools in the Annapolis area along with other great amenities.