Vacation Rentals in Annapolis, MD
PRICE PER NIGHT
ACCOMMODATION TYPES
Beautiful Historic Home With Great Location!
10
Excellent
·
Annapolis
·
4 br
·
Free Parking · Fireplace · Outdoor Space ·
From
$350/nightProperty
House · 4 Beds · 3 baths
Amenities
Free Parking
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Waterfront Chesapeake Cottage in Oyster Bay - Dock
9.8
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
Central Heat · Toiletries · Tv ·
From
$200/nightProperty
House · 3 Beds · 2 baths
Amenities
Central Heat
Toiletries
Tv
Waterfront
Beach
Free Parking
Wifi
Other spaces
Kitchen
Chic Condo w/ Balcony in the Heart of Annapolis!
9.7
Excellent
·
Annapolis
·
2 br
·
Sleeps 6
·
Cable · Microwave · Toiletries ·
From
$110/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Cable
Microwave
Toiletries
Walk In Closets
Tv
Dishwasher
Wifi
Oven
Other spaces
Kitchen
Private Pet-friendly Coastal Suite with water views just minutes to Annapolis
9.5
Excellent
·
Annapolis
·
2 br
·
Sleeps 4
·
Beach · Fitness Center · Dishwasher ·
From
$312/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Beach
Fitness Center
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
7 mins away from Downtown Annapolis
No reviews
·
Annapolis
·
6 br
·
Sleeps 11
·
Air Conditioning · Furnished · In Unit Laundry ·
From
$450/nightProperty
House · 6 Beds · 2 baths
Amenities
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Indoor/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!
9.8
Excellent
·
Annapolis
·
5 br
·
Sleeps 16
·
Carpet · Pool · Private Pool ·
From
$1,150/nightProperty
House · 5 Beds · 4 baths
Amenities
Carpet
Pool
Private Pool
Waterfront
Assigned Parking
Fireplace
Dishwasher
Air Conditioning
Other spaces
Balcony, Workspace, Kitchen
Private Single Family Home Close to Both Water and Downtown!
9.2
Excellent
·
Annapolis
·
4 br
·
Sleeps 7
·
Beach · Free Parking · Assigned Parking ·
From
$748/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Beach
Free Parking
Assigned Parking
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
Anchors Aweigh
No reviews
·
Annapolis
·
4 br
·
Sleeps 8
·
On Site Laundry · Dishwasher · Air Conditioning ·
From
$637/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
On Site Laundry
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
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The King's Court
No reviews
·
Annapolis
·
4 br
·
Sleeps 8
·
On Site Laundry · Dishwasher · Air Conditioning ·
From
$418/nightProperty
Apartment · 4 Beds · 4 baths
Amenities
On Site Laundry
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Blue Angel's Nest
9
Excellent
·
Annapolis
·
4 br
·
Sleeps 10
·
On Site Laundry · Fireplace · Dishwasher ·
From
$555/nightProperty
Apartment · 4 Beds · 4 baths
Amenities
On Site Laundry
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
The Pacific Fleet House
No reviews
·
Annapolis
·
5 br
·
Sleeps 10
·
On Site Laundry · Fireplace · Dishwasher ·
From
$679/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
On Site Laundry
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Annapolis Vacation Home 2 Mi to Quiet Waters Park
No reviews
·
Annapolis
·
4 br
·
Sleeps 8
·
Free Parking · Fireplace · Dishwasher ·
From
$303/nightProperty
Apartment · 4 Beds · 4 baths
Amenities
Free Parking
Fireplace
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
The Little House
4
Good
·
Annapolis
·
2 br
·
Sleeps 4
·
On Site Laundry · Outdoor Space · Dishwasher ·
From
$306/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
On Site Laundry
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Cozy Yellow House
No reviews
·
Annapolis
·
2 br
·
Sleeps 4
·
On Site Laundry · Outdoor Space · Dishwasher ·
From
$373/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
On Site Laundry
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Stroll to Downtown Annapolis and all it has to offer
No reviews
·
Annapolis
·
4 br
·
Sleeps 12
·
Workspace · Dishwasher · Air Conditioning ·
From
$541/nightProperty
House · 4 Beds · 2 baths
Amenities
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Workspace, Kitchen
Spacious Downtown Getaway- Across from US Naval Academy
9.7
Excellent
·
Annapolis
·
2 br
·
Sleeps 6
·
Dishwasher · Air Conditioning · Furnished ·
From
$261/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Business Center
Other spaces
Kitchen
Charming Downtown 3rd Floor 1 Bedroom Apt
10
Excellent
·
Annapolis
·
1 br
·
Sleeps 4
·
Outdoor Space · Air Conditioning · Furnished ·
From
$191/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Business Center
Other spaces
Kitchen
#theMidShip,downtown,parking,petfamilyfriendly
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 9
·
Free Parking · Workspace · Dishwasher ·
From
$726/nightProperty
House · 3 Beds · 2 baths
Amenities
Free Parking
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Workspace, Kitchen
MODERN 2022 NEWLY BUILT TOWNHOME
No reviews
·
Annapolis
·
3 br
·
Sleeps 8
·
Walk In Closets · Balcony · Fireplace ·
From
$700/nightProperty
House · 3 Beds · 4 baths
Amenities
Walk In Closets
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Balcony, Workspace, Kitchen
Seashell in the City 2 parking spots and Walkable to Main Street!
10
Excellent
·
Annapolis
·
4 br
·
Sleeps 8
·
Fitness Center · Outdoor Space · Dishwasher ·
From
$519/nightProperty
House · 4 Beds · 3 baths
Amenities
Fitness Center
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Quaint 2BR/2.5 BA water view home with parking!
10
Excellent
·
Annapolis
·
2 br
·
Sleeps 4
·
Fireplace · Workspace · Dishwasher ·
From
$583/nightProperty
House · 2 Beds · 3 baths
Amenities
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Oven
Other spaces
Workspace, Kitchen
Steps to Main Street w View of the Capital private back patio & off-site parking
9.9
Excellent
·
Annapolis
·
4 br
·
Sleeps 8
·
Assigned Parking · Fitness Center · Workspace ·
From
$434/nightProperty
House · 4 Beds · 3 baths
Amenities
Assigned Parking
Fitness Center
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Workspace, Kitchen
3 Parking Spots at Lux Red Door Gem
No reviews
·
Annapolis
·
5 br
·
Sleeps 10
·
Ev Charging · Hardwood Floor · Fireplace ·
From
$1,375/nightProperty
House · 5 Beds · 4 baths
Amenities
Ev Charging
Hardwood Floor
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
Historic Fisher House steps to Main St with parking and private back patio!
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 9
·
Assigned Parking · Fitness Center · Fireplace ·
From
$398/nightProperty
House · 3 Beds · 2 baths
Amenities
Assigned Parking
Fitness Center
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
3 parking spots and private patio at Hansel & Gretel home in downtown Annapolis
9.8
Excellent
·
Annapolis
·
2 br
·
Sleeps 7
·
Fitness Center · Fireplace · Outdoor Space ·
From
$367/nightProperty
House · 2 Beds · 2 baths
Amenities
Fitness Center
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Downtown Annapolis Row House
9
Excellent
·
Annapolis
·
3 br
·
Sleeps 6
·
Workspace · Outdoor Space · Dishwasher ·
From
$275/nightProperty
House · 3 Beds · 2 baths
Amenities
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Workspace, Kitchen
Charming garden row home, easy 4 block walk to the heart of Annapolis.
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 6
·
Outdoor Space · Dishwasher · Air Conditioning ·
From
$351/nightProperty
House · 3 Beds · 2 baths
Amenities
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Family Tribute Marine's Gate across from Gate 1
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 6
·
On Site Laundry · Fitness Center · Fireplace ·
From
$447/nightProperty
House · 3 Beds · 4 baths
Amenities
On Site Laundry
Fitness Center
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
9.4
Excellent
·
Annapolis
·
1 br
·
Sleeps 2
·
Outdoor Space · Air Conditioning · Furnished ·
From
$188/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Waterfront Chesapeake Cottage in Oyster Bay - Dock
9.8
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
High Ceilings · Central Heat · Waterfront ·
From
$638/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
High Ceilings
Central Heat
Waterfront
Beach
Fireplace
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Kitchen
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
10
Excellent
·
Annapolis
·
4 br
·
Sleeps 8
·
Cable · Microwave · Toiletries ·
From
$218/nightProperty
House · 4 Beds · 4 baths
Amenities
Cable
Microwave
Toiletries
Tv
Free Parking
Fireplace
Dishwasher
Wifi
Other spaces
Kitchen
Take your Leave of Absence around gardens with a private driveway
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 9
·
Balcony · On Site Laundry · Fitness Center ·
From
$948/nightProperty
House · 3 Beds · 3 baths
Amenities
On Site Laundry
Fitness Center
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Balcony, Workspace, Kitchen
We Get Repeat Renters!!
10
Excellent
·
Annapolis
·
4 br
·
Sleeps 8
·
Hardwood Floor · Fitness Center · Dishwasher ·
From
$680/nightProperty
House · 4 Beds · 4 baths
Amenities
Hardwood Floor
Fitness Center
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Lots free parking, hot tub, tree house, outdoor oasis - NOT party house
9.5
Excellent
·
Annapolis
·
4 br
·
Sleeps 10
·
Hot Tub · Hardwood Floor · Free Parking ·
From
$567/nightProperty
House · 4 Beds · 3 baths
Amenities
Hot Tub
Hardwood Floor
Free Parking
On Site Laundry
Fitness Center
Fireplace
Dishwasher
Air Conditioning
Other spaces
Kitchen
Freshly renovated 3-story home 1 block from USNA!
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 10
·
Balcony · Hardwood Floor · Fireplace ·
From
$125/nightProperty
House · 3 Beds · 3 baths
Amenities
Hardwood Floor
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Balcony, Workspace, Kitchen
Lovely historic home with patio, central AC, full kitchen & washer/dryer
No reviews
·
Annapolis
·
3 br
·
Sleeps 6
·
Workspace · Dishwasher · Air Conditioning ·
From
$365/nightProperty
House · 3 Beds · 2 baths
Amenities
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Oven
Other spaces
Workspace, Kitchen
Duke's Den Downtown home with 2 PARKING spots!
9.9
Excellent
·
Annapolis
·
4 br
·
Sleeps 14
·
Walk In Closets · Hardwood Floor · Assigned Parking ·
From
$904/nightProperty
House · 4 Beds · 4 baths
Amenities
Walk In Closets
Hardwood Floor
Assigned Parking
On Site Laundry
Fitness Center
Dishwasher
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Historic happy home on quiet City street, steps to Main Street, parking and lots of outdoor space
No reviews
·
Annapolis
·
3 br
·
Assigned Parking · On Site Laundry · Fitness Center ·
From
$539/nightProperty
House · 3 Beds · 3 baths
Amenities
Assigned Parking
On Site Laundry
Fitness Center
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
New Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 6
·
On Site Laundry · Fitness Center · Outdoor Space ·
From
$790/nightProperty
House · 3 Beds · 4 baths
Amenities
On Site Laundry
Fitness Center
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
High-end Eastport home with private pool, hot tub, grill & off-street parking
No reviews
·
Annapolis
·
4 br
·
Sleeps 8
·
Pool · Private Pool · Hot Tub ·
From
$756/nightProperty
House · 4 Beds · 3 baths
Amenities
Pool
Private Pool
Hot Tub
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
Historic Downtown Annapolis Home for Rent- Steps to Naval Academy
10
Excellent
·
Annapolis
·
4 br
·
Sleeps 11
·
Assigned Parking · Dishwasher · Air Conditioning ·
From
$540/nightProperty
House · 4 Beds · 3 baths
Amenities
Assigned Parking
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Stay in USNA-themed home steps from Navy Stadium
10
Excellent
·
Annapolis
·
3 br
·
Hot Tub · On Site Laundry · Fitness Center ·
From
$433/nightProperty
House · 3 Beds · 2 baths
Amenities
Hot Tub
On Site Laundry
Fitness Center
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Workspace, Kitchen
a charming 2 bedrooms home in historic Annapolis with parking!!
9.8
Excellent
·
Annapolis
·
2 br
·
Sleeps 6
·
Workspace · Outdoor Space · Dishwasher ·
From
$223/nightProperty
House · 2 Beds · 2 baths
Amenities
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Workspace, Kitchen
Annapolis steps to Harbor and Naval Academy
8.7
Very good
·
Annapolis
·
1 br
·
Sleeps 4
·
Waterfront · Assigned Parking · Workspace ·
From
$242/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Waterfront
Assigned Parking
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Workspace, Kitchen
Walk to Waterfront & USNA with Parking at Historic Wisteria
9.8
Excellent
·
Annapolis
·
4 br
·
Sleeps 7
·
Assigned Parking · Fitness Center · Dishwasher ·
From
$409/nightProperty
House · 4 Beds · 4 baths
Amenities
Assigned Parking
Fitness Center
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Stunning, Large Historic Annapolis Home, Steps to Academy and Downtown.
No reviews
·
Annapolis
·
5 br
·
Sleeps 12
·
Carpet · Balcony · Hardwood Floor ·
From
$1,000/nightProperty
House · 5 Beds · 4 baths
Amenities
Carpet
Hardwood Floor
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Spacious 4 BR Annapolis retreat
10
Excellent
·
Annapolis
·
4 br
·
Sleeps 8
·
Beach · Outdoor Space · Dishwasher ·
From
$442/nightProperty
House · 4 Beds · 4 baths
Amenities
Beach
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
“Athens of America,” Annapolis Apartment Two B
8.3
Very good
·
Annapolis
·
1 br
·
Sleeps 4
·
Air Conditioning · Furnished · In Unit Laundry ·
From
$160/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Eastport Cottage .5 mi from Downtown Annapolis
10
Excellent
·
Annapolis
·
2 br
·
Sleeps 3
·
Workspace · Outdoor Space · Dishwasher ·
From
$369/nightProperty
House · 2 Beds · 1 bath
Amenities
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Workspace, Kitchen
Luxury home! 1 mi from USNA! 3 Bd/3.5 Ba with Private Heated & Salted Pool!
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
Pool · Private Pool · Dishwasher ·
From
$814/nightProperty
House · 3 Beds · 4 baths
Amenities
Pool
Private Pool
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
Showing 1 - 50 of 310 results
Updated: March 27, 2023
Learn about vacation rentals in
Annapolis
Explore 311 vacation rentals near Annapolis, Maryland. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Annapolis, you can see photos of Annapolis vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Annapolis vacation rentals in specific areas. Whether you’re looking for a Annapolis staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Annapolis is $110 per night and the highest price is $1,375 per night.
63 of the vacation rentals near Annapolis are
apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation
units is $191 per night. There are
currently 25 vacation units under this
price. 233 of the vacation rentals near Annapolis are houses.
The average bathroom count for a vacation house near Annapolis is
3. The average price for vacation houses near Annapolis is $548 per night. There are 143 vacation homes under this price. The most common
amenities for vacation rentals near Annapolis are: furnished, kitchen, and oven. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
51 available
2 bed rentals
70 available
3 bed rentals
91 available
4+ bed rentals
97 available
Getting around Annapolis
Walking
5/10
Some shops and stores are within a few minutes.
Car
8/10
Commuting is easy with multiple accessible routes and plenty of parking.
Transit
3/10
There are a few mass transit options within the area.
Points of interest in Annapolis
Groceries
5/10
At least one grocery store within a 30-minute walk
Shopping
5/10
Variety of shops within walking distance
Cafes
4/10
Some cafés within walking distance
Restaurants
5/10
Some restaurants within walking distance
Parks
5/10
Moderate amount of park space nearby
Nightlife
3/10
Few or no bars within walking distance
Vacation Rentals in Annapolis, MD FAQ
How many vacation rentals in Annapolis are available?
There are currently 311 vacation rentals in Annapolis available. Our vacation rentals in Annapolis include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Annapolis?
Yes, right now there are 75 pet friendly vacation rentals in Annapolis. A pet friendly vacation rental in Annapolis means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Annapolis with a pool?
Yes there are vacation rentals with a pool available in Annapolis, MD. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Annapolis with internet access?
As of March 27, 2023, there are vacation rentals with internet access available in Annapolis, Maryland. Check out more enjoyable destinations on Vacations by Zumper.
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