Stays for 8+ guests in Annapolis, MD
Stays for 8+ guests in Annapolis, MD, from $404 a night. Book direct on each manager's site, no OTA fee.
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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
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
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
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
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 2026-10-29 18:40 UTC. Prices and facts are whatever the manager published on their own site.