Vacation Rentals in Annapolis, MD

335 rentals

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Annapolis, MD

Book a vacation rental in Annapolis that has the highest visitor rating. Here are 6 of the best vacation rentals in Annapolis.
Stunning Waterfront Cottage with Breathtaking Views!
10

Excellent

·
Annapolis
·
2 br
·
Sleeps 6
·
Waterfront · Kitchen · Air Conditioning ·
From
$371/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Waterfront
Air Conditioning
Hardwood Floor
Furnished
In Unit Laundry
Fitness Center
Oven
Dishwasher
Other spaces
Kitchen, Outdoor Space
Waterfront Oasis in Eastport - Walk to Downtown and USNA
10

Excellent

·
Annapolis
·
5 br
·
Sleeps 10
·
Wifi · Oven · In Unit Laundry ·
From
$475/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Wifi
Oven
In Unit Laundry
Furnished
Dishwasher
Waterfront
Air Conditioning
Other spaces
Kitchen, Outdoor Space
Large Luxury Apartment In Downtown Annapolis
10

Excellent

·
Annapolis
·
2 br
·
Sleeps 4
·
Dishwasher · Wifi · Air Conditioning ·
From
$367/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Dishwasher
Wifi
Air Conditioning
Furnished
Oven
On Site Laundry
In Unit Laundry
Fitness Center
Other spaces
Kitchen, Outdoor Space
PERFECT LOCATION in the heart of history
10

Excellent

·
Annapolis
·
3 br
·
Sleeps 8
·
Outdoor Space · Fitness Center · Dishwasher ·
From
$345/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Fitness Center
Dishwasher
Wifi
Air Conditioning
Business Center
Hardwood Floor
Wheelchair Accessible
In Unit Laundry
Other spaces
Outdoor Space, Kitchen, Workspace
Restriction Retreat - Relax & walk to Main St
10

Excellent

·
Annapolis
·
2 br
·
Sleeps 6
·
Furnished · Workspace · Kitchen ·
From
$511/night
Check availability
Property
House · 2 Beds · 3 baths
Amenities
Furnished
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Wifi
Other spaces
Workspace, Kitchen
Fisher House - Downtown Annapolis!
10

Excellent

·
Annapolis
·
3 br
·
Sleeps 9
·
In Unit Laundry · Air Conditioning · Oven ·
From
$459/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
In Unit Laundry
Air Conditioning
Oven
Dishwasher
Furnished
Wifi
Other spaces
Kitchen, Outdoor Space

Budget-Friendly Vacation Rentals in Annapolis, MD

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Annapolis starting at $66. Use the price filter at the top of the page to search for more specific prices.
16 Silverwood Cir

No rating

·
Annapolis
·
2 br
·
Swimming Pool · Air Conditioning · Storage ·
From
$66/night
Min stay: 30 nights
Property
Condo · 2 Beds · 2 baths
Amenities
Swimming Pool
Air Conditioning
Storage
In Unit Laundry
Other spaces
Walk In Closets, Balcony
Charming Downtown 3rd Floor 1 Bedroom Apt
10

Excellent

·
Annapolis
·
1 br
·
Sleeps 4
·
Furnished · Wifi · In Unit Laundry ·
From
$81/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Wifi
In Unit Laundry
Business Center
Oven
Air Conditioning
Other spaces
Kitchen, Outdoor Space
Convenient Eastport condo with beautiful water views and community pool!

No rating

·
Annapolis
·
1 br
·
Sleeps 2
·
Furnished · Pool · Air Conditioning ·
From
$83/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
Furnished
Pool
Air Conditioning
Waterfront
Business Center
Swimming Pool
Oven
Fireplace
Hilton Garden Inn Annapolis Downtown
8

Very good

·
Annapolis
·
1 br
·
Sleeps 4
·
Residents Lounge · Smoking Allowed · Storage ·
From
$88/night
Check availability
Property
Hotel · 1 Bed
Amenities
Residents Lounge
Smoking Allowed
Storage
On Site Laundry
Wifi
Business Center
Air Conditioning
Fitness Center
Other spaces
Outdoor Space, Workspace
The Westin Annapolis
8.3

Very good

·
Annapolis
·
1 br
·
Sleeps 4
·
Assigned Parking · Swimming Pool · Storage ·
From
$89/night
Check availability
Property
Hotel · 1 Bed
Amenities
Assigned Parking
Swimming Pool
Storage
Fitness Center
On Site Laundry
Dry Cleaning Service
Air Conditioning
Pool
Other spaces
Workspace
Amazing Bright Big Window Loft Heart of Eastport

No rating

·
Annapolis
·
1 br
·
Sleeps 2
·
Furnished · Oven · In Unit Laundry ·
From
$90/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Oven
In Unit Laundry
Fitness Center
Elevator
Dishwasher
Air Conditioning
Wifi
Other spaces
Outdoor Space, Kitchen

Family-Friendly Vacation Rentals in Annapolis, MD

Heading to Annapolis for your next family vacation? Check out these family-friendly vacation rentals, which have more bedrooms and more space for you and your loved ones. Use the filters at the top of the page to narrow your search and find what you need.
Gracie's Garden in Annapolis

No rating

·
Annapolis
·
1 br
·
Sleeps 4
·
Wifi · Air Conditioning · Outdoor Space ·
From
$268/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Air Conditioning
Residents Lounge
Furnished
Business Center
Free Parking
In Unit Laundry
Oven
Other spaces
Outdoor Space, Kitchen, Workspace
Luxurious apartment with gourmet kitchen in Eastport

No rating

·
Annapolis
·
1 br
·
Sleeps 2
·
Oven · Workspace · Air Conditioning ·
From
$352/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Oven
Air Conditioning
Dishwasher
Furnished
Fitness Center
Wifi
In Unit Laundry
Other spaces
Workspace, Kitchen, Outdoor Space
Anchor's Away in the Heart of Eastport!
10

Excellent

·
Annapolis
·
1 br
·
Sleeps 3
·
Air Conditioning · Dishwasher · Wifi ·
From
$188/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
Air Conditioning
Dishwasher
Wifi
Storage
High Ceilings
Fireplace
In Unit Laundry
Furnished
Other spaces
Outdoor Space, Kitchen, Workspace
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Updated: February 29, 2024