Stays in Annapolis, MD
Stays in Annapolis, MD, from $100 a night. Book direct on each manager's site, no OTA fee.
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Strohm House Annapolis
House · 3 bed · 3 bath · sleeps 5
Annapolis, MD
From $130 a night
- fully furnished
- bi-weekly housekeeping included
- full kitchen
- free wi-fi
Exact location
Book direct on Annapolis Legislative Housing
Crew's Quarters
House · 3 bed · 1.5 bath · sleeps 6
Annapolis, MD
From $100 a night
- no smoking.
Exact location
Book direct on CielStay
Brand New Reno in Historic Dist w 2 Parking spots
House · 2 bed · 1 bath · sleeps 4
Annapolis, MD
From $312 a night
- air conditioning
- bedsheets provided
- dining area
- fireplace
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
6 Mi to Dtwn: Family-Friendly Home in Annapolis!
House · 5 bed · 3 bath · sleeps 12
Annapolis, MD
From $404 a night
- air conditioning
- barbecue grill
- books
- deck or patio
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Holiday Rentals Home (HRH)
House · 4 bed · 4 bath · sleeps 12
Annapolis, MD
From $404 a night
- air conditioning
- bedsheets provided
- deck or patio
- dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Holiday Rentals Home (HRH)
House · 5 bed · 3 bath · sleeps 12
Annapolis, MD
From $404 a night
- air conditioning
- barbecue grill
- bedsheets provided
- deck or patio
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Chesapeake Room
Hotel
Annapolis, MD
From $225 a night
Exact location
Book direct on Capital Hotel Annapolis: Lodging near Downtown Annapolis Maryland
Cape Saint Claire
Beach house · 2 bed
Annapolis, MD
From $100 a night
- reception services
- room services
- internet
- toiletries
City-level location
Book direct on Luxury Vacation Rentals Anywhere in the World
Furnished Corporate Housing in Annapolis | Izeal Stay
Apartment · 5 bed · 3 bath
Annapolis, MD
From $180 a night
City-level location
Book direct on Furnished Apartments and Corporate Housing USA
Airbnb Marketing in Annapolis
Annapolis, MD
From $285 a night
- 01 services 30
- 02 locations all
- 03 clients 24
- 04 resources 17
City-level location
Book direct on Airbnb Marketing Agency for Vacation Rentals
4BR Family Retreat Near Annapolis w/ Large Yard
House · 4 bed · 2 bath · sleeps 16
Annapolis, MD
No nightly rate published
- 24 checkin
- air conditioning
- baking sheet
- barbecue
Exact location
Book direct on Vacation Rentals in Annapolis, Ocean City & Florida
Coastal Comfort
Farmhouse · 4 bed · 2.5 bath · sleeps 8
Annapolis, MD
No nightly rate published
- air conditioning
- fireplace
- central heating
- baking sheet
Exact location
Book direct on Hygge Hosting and Design
Coastal Quarters
Farmhouse · 4 bed · 3 bath · sleeps 8
Annapolis, MD
No nightly rate published
- air conditioning
- central heating
- baking sheet
- blender
Exact location
Book direct on Hygge Hosting and Design
Eastport Bungalow | Yard, Grill & Walk Downtown
Bungalow · 4 bed · 3 bath · sleeps 8
Annapolis, MD
No nightly rate published
- 24 checkin
- air conditioning
- baking sheet
- balcony terrasse
Exact location
Book direct on Vacation Rentals in Annapolis, Ocean City & Florida
Historic Downtown Annapolis Gem Near USNA
House · 3 bed · 2 bath · sleeps 16
Annapolis, MD
No nightly rate published
- 24 checkin
- air conditioning
- baking sheet
- barbecue
Exact location
Book direct on Vacation Rentals in Annapolis, Ocean City & Florida
Luxury Eastport Home w/ Chef’s Kitchen, Sleeps 16
House · 3 bed · 4 bath · sleeps 16
Annapolis, MD
No nightly rate published
- 24 checkin
- air conditioning
- baking sheet
- balcony terrasse
Exact location
Book direct on Vacation Rentals in Annapolis, Ocean City & Florida
Pet Friendly Retreat Near Downtown Annapolis
House · 3 bed · 1 bath · sleeps 16
Annapolis, MD
No nightly rate published
- 24 checkin
- air conditioning
- baking sheet
- bidet
Exact location
Book direct on Vacation Rentals in Annapolis, Ocean City & Florida
Plebe's Paradise
Farmhouse · 2 bed · 2.5 bath · sleeps 6
Annapolis, MD
No nightly rate published
- air conditioning
- central heating
- baking sheet
- coffee maker
Exact location
Book direct on Hygge Hosting and Design
Renovated Downtown Annapolis w/ 3-Car Parking
House · 3 bed · 2 bath · sleeps 16
Annapolis, MD
No nightly rate published
- 24 checkin
- air conditioning
- baking sheet
- blender
Exact location
Book direct on Vacation Rentals in Annapolis, Ocean City & Florida
STAYdium House
House · 4 bed · 3 bath · sleeps 8
Annapolis, MD
No nightly rate published
- air conditioning
- central heating
- baking sheet
- blender
Exact location
Book direct on Hygge Hosting and Design
Spa Creek Cottage – Walk to Downtown Annapolis
Cottage · 5 bed · 2 bath · sleeps 16
Annapolis, MD
No nightly rate published
- 24 checkin
- activity antiquing
- activity bay
- activity boating
Exact location
Book direct on Vacation Rentals in Annapolis, Ocean City & Florida
Gallant Fox Room
Suite · sleeps 2
Annapolis, MD
No nightly rate published
- curated concierge services
- heated bathroom flooring
- tile bathroom with shower & bathtub
- complimentary wi-fi
City-level location
Book direct on Luxury Boutique Hotel
Hot Tub EV Charger DogsOK 50"TV Fire Pit Gas Grill
House · 5 bed · 4 bath · sleeps 12
Annapolis, MD
No nightly rate published
City-level location
Book direct on Stay Bubo Annapolis
Presidential Suite
Suite · sleeps 2
Annapolis, MD
No nightly rate published
- curated concierge services
- complimentary locally- sourced breakfast
- nespresso coffee machine
- complimentary wi-fi
City-level location
Book direct on Luxury Boutique Hotel
Queen Rooms III | IV | V
Suite · sleeps 2
Annapolis, MD
No nightly rate published
- curated concierge services
- heated bathroom flooring
- complimentary wi-fi
- 4k flat-screen tv
City-level location
Book direct on Luxury Boutique Hotel
Annapolis Luxury: Firepit | Deck | Grill
Townhome · 3 bed · 3 bath
Annapolis, MD
No nightly rate published
City-level location
Book direct on Chesapeake Vacation Rental Homes
Hot Tub Dogs OK Fire Pit Gas Grill Wood Stove Roku
Cabin · 4 bed · 2 bath
Annapolis, MD
No nightly rate published
City-level location
Book direct on Stay Bubo Annapolis
Hot Tub Pool Table 65"TV Pool Tennis Hiking Golf
House · 6 bed · 4 bath
Annapolis, MD
No nightly rate published
City-level location
Book direct on Stay Bubo Annapolis
♛Royal A-Frame♛HOT TUB★PetsOK★WoodStove★FASTwifi
Cabin · 3 bed · 1 bath
Annapolis, MD
No nightly rate published
City-level location
Book direct on Stay Bubo Annapolis
Commodore Suite
House · sleeps 2
Annapolis, MD
No nightly rate published
City-level location
Book direct on Flag House Inn
How prices are computed
Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.
Updated 2026-10-30 05:35 UTC. Prices and facts are whatever the manager published on their own site.