Annapolis Cottage Rentals & Holiday Homes
Find the best cottages in Annapolis - We found 39 exact matches
About Annapolis Luxury Rental on Gulf Blue Vacations
Searching for cottages to rent near Annapolis? Gulf Blue Vacations features more than 39 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. Gulf Blue Vacations’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? Gulf Blue Vacations’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.
Gulf Blue Vacations boasts of 39 holiday cottages and places to stay in Annapolis. The site provides unique Airbnb, VRBO, Gulf Blue Vacations-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 Annapolis Cottage Rentals
What are the top rated Cottage Rentals 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:
- Wonderful Cottage Nestled On Chesapeake Bay
- Peaceful Escape: Bay Ridge Cottage by the Bay
- Idyllic Cottage Near Annapolis with Treehouse Vibes & Outdoor Charm
- Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
- 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!
- Cozy Nautical Cottage in Annapolis w/Beautiful Outdoor Space
- Waterfront Chesapeake Cottage in Oyster Bay - Dock
How much does it cost to rent a cottage in Annapolis?
The average cost for a cottage rental in Annapolis is $460 per night. Gulfbluevacations 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.
Are there any cottages in Annapolis that allow pets?
Yes, here are the top cottage rentals in Annapolis that allow you to bring your pet:
- Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
- Weems Creek Cottage, Annapolis Waterfront
- The Yellow Cottage on Harness Creek
- Chesapeake Bay Views and Private Deck Cozy Cottage
See all pet-friendly vacation rentals in Annapolis on Gulfbluevacations
Do you have any rental cottages in Annapolis that are suitable for families?
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.
Are there quality cottages in Annapolis that have indoor swimming pools?
As of 2026, the data from Gulfbluevacations shows that there are Over 39 private swimming pools or cottages with indoor pools in the Annapolis area along with other great amenities.
