Vacation Rentals in Annapolis, MD
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.
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Admiral's Glen
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
Furnished · Air Conditioning · Wifi ·
From
$427/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Furnished
Air Conditioning
Wifi
Dishwasher
Oven
On Site Laundry
Other spaces
Kitchen
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
10
Excellent
·
Annapolis
·
5 br
·
Sleeps 10
·
Wifi · Oven · Furnished ·
From
$712/nightProperty
House · 5 Beds · 4 baths
Amenities
Wifi
Oven
Furnished
Waterfront
Air Conditioning
Dishwasher
On Site Laundry
Other spaces
Kitchen
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PERFECT LOCATION in the heart of history
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
Kitchen · Air Conditioning · Fitness Center ·
From
$328/nightProperty
House · 3 Beds · 3 baths
Amenities
Air Conditioning
Fitness Center
Wheelchair Accessible
On Site Laundry
Business Center
Furnished
Hardwood Floor
Dishwasher
Other spaces
Kitchen, Workspace
Cozy Home in Beautiful Annapolis
10
Excellent
·
Annapolis
·
2 br
·
Sleeps 4
·
Kitchen · On Site Laundry · Air Conditioning ·
From
$162/nightProperty
House · 2 Beds · 1 bath
Amenities
On Site Laundry
Air Conditioning
Oven
Furnished
Wifi
Other spaces
Kitchen, Workspace
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
10
Excellent
·
Annapolis
·
2 br
·
Sleeps 4
·
Kitchen · Dishwasher · Hardwood Floor ·
From
$250/nightProperty
House · 2 Beds · 2 baths
Amenities
Dishwasher
Hardwood Floor
On Site Laundry
Fireplace
Furnished
Air Conditioning
Oven
Assigned Parking
Other spaces
Kitchen
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Annapolis Vacation Home: 2 Mi to Quiet Waters Park
10
Excellent
·
Annapolis
·
4 br
·
Sleeps 8
·
Air Conditioning · Fireplace · Walk In Closets ·
From
$334/nightProperty
House · 4 Beds · 4 baths
Amenities
Air Conditioning
Fireplace
Walk In Closets
Oven
On Site Laundry
Dishwasher
Furnished
Wifi
Other spaces
Kitchen
Our Recommended Vacation Rentals in Annapolis, MD
We analyzed vacation rentals in Annapolis from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Annapolis to help you find a deal for your next trip.
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Private Single Family Home Close to Both Water and Downtown!
9.2
Excellent
·
Annapolis
·
4 br
·
Sleeps 7
·
Outdoor Space · Furnished · Wifi ·
From
$606/nightProperty
House · 4 Beds · 3 baths
Amenities
Furnished
Wifi
Beach
Air Conditioning
Oven
On Site Laundry
Assigned Parking
Dishwasher
Other spaces
Workspace, Kitchen
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Anchors Aweigh
No rating
·
Annapolis
·
4 br
·
Sleeps 8
·
Kitchen · Oven · Wifi ·
From
$936/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Oven
Wifi
Furnished
Air Conditioning
On Site Laundry
Dishwasher
Other spaces
Kitchen
Price drop
Blue Angel's Nest
9
Excellent
·
Annapolis
·
4 br
·
Sleeps 10
·
Dishwasher · Air Conditioning · Furnished ·
From
$865/nightProperty
Apartment · 4 Beds · 4 baths
Amenities
Dishwasher
Air Conditioning
Furnished
On Site Laundry
Fireplace
Oven
Wifi
Other spaces
Kitchen
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Harrison Hall
No rating
·
Annapolis
·
4 br
·
Sleeps 8
·
On Site Laundry · Fireplace · Outdoor Space ·
From
$885/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
On Site Laundry
Fireplace
Air Conditioning
Wifi
Furnished
Oven
Dishwasher
Other spaces
Kitchen
Price drop
The Pacific Fleet House
No rating
·
Annapolis
·
5 br
·
Sleeps 10
·
Air Conditioning · Furnished · Kitchen ·
From
$1,047/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
Air Conditioning
Furnished
Oven
Fireplace
Wifi
On Site Laundry
Dishwasher
Other spaces
Kitchen
Price drop
The Little House
4
Good
·
Annapolis
·
2 br
·
Sleeps 4
·
Oven · Kitchen · Outdoor Space ·
From
$380/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Oven
Dishwasher
On Site Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
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 $79. Use the price filter at the top of the page to search for more specific prices.
Eastport condo is located in a waterfront community with a community pool & picnic/grilling area
No rating
·
Annapolis
·
1 br
·
Sleeps 2
·
Furnished · Outdoor Space · In Unit Laundry ·
From
$79/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Furnished
In Unit Laundry
Elevator
Swimming Pool
Assigned Parking
Air Conditioning
Pool
Oven
Other spaces
Workspace
Convenient Eastport condo with beautiful water views and community pool!
No rating
·
Annapolis
·
1 br
·
Sleeps 2
·
Furnished · Pool · Air Conditioning ·
From
$83/nightProperty
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/nightProperty
Hotel · 1 Bed
Amenities
Residents Lounge
Smoking Allowed
Storage
On Site Laundry
Wifi
Business Center
Air Conditioning
Fitness Center
Other spaces
Workspace
The Westin Annapolis
8.3
Very good
·
Annapolis
·
1 br
·
Sleeps 4
·
Assigned Parking · Swimming Pool · Storage ·
From
$89/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Swimming Pool
Storage
Fitness Center
On Site Laundry
Dry Cleaning Service
Air Conditioning
Pool
Other spaces
Workspace
Graduate Annapolis
9.1
Excellent
·
Annapolis
·
1 br
·
Sleeps 10
·
Assigned Parking · Residents Lounge · Furnished ·
From
$93/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Residents Lounge
Furnished
On Site Laundry
Dry Cleaning Service
Air Conditioning
Storage
Fitness Center
Other spaces
Workspace
Historic Inns of Annapolis
8.2
Very good
·
Annapolis
·
1 br
·
Sleeps 4
·
Concierge Service · Residents Lounge · Wifi ·
From
$95/nightProperty
Hotel · 1 Bed
Amenities
Concierge Service
Residents Lounge
Wifi
Fitness Center
Assigned Parking
Smoking Allowed
Storage
On Site Laundry
Other spaces
Workspace
Vacation Rentals With A Pool in Annapolis, MD
Want to relax by the pool? Book one of these Annapolis vacation rentals with a pool.
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Waterfront Yacht Life!
10
Excellent
·
Annapolis
·
3 br
·
Sleeps 4
·
Air Conditioning · Waterfront · Residents Lounge ·
From
$359/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Air Conditioning
Waterfront
Residents Lounge
Swimming Pool
Furnished
On Site Laundry
Pool
Oven
Other spaces
Kitchen, Workspace
Price drop
Waterfront Condo with pool and parking walkable to all of DTA
10
Excellent
·
Annapolis
·
2 br
·
Sleeps 7
·
Pool · Balcony · Oven ·
From
$338/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Pool
Oven
Wifi
On Site Laundry
Swimming Pool
Air Conditioning
Elevator
Furnished
Other spaces
Balcony, Kitchen
Chill in Mellow Yellow with PARKING!
10
Excellent
·
Annapolis
·
1 br
·
Sleeps 4
·
Kitchen · Fitness Center · Wifi ·
From
$238/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Wifi
Swimming Pool
On Site Laundry
Oven
Furnished
Air Conditioning
Hot Tub
Other spaces
Kitchen
Vacation Rentals With AC and/or Heat in Annapolis, MD
Whether you need air conditioning or central heating, these vacation rentals are for you.
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Waterfront Chesapeake Cottage in Oyster Bay - Dock
9.8
Excellent
·
Annapolis
·
3 br
·
Sleeps 8
·
Cable · Kitchen · Outdoor Space ·
From
$470/nightProperty
House · 3 Beds · 2 baths
Amenities
Cable
Air Conditioning
Beach
Tv
Wifi
Assigned Parking
Toiletries
Oven
Other spaces
Kitchen
Annapolis Oasis: Home Theater & Screened Porch
No rating
·
Annapolis
·
3 br
·
Sleeps 8
·
Furnished · Workspace · Oven ·
From
$236/nightProperty
House · 3 Beds · 2 baths
Amenities
Furnished
Oven
Fireplace
Air Conditioning
Central Heat
Wifi
Ceiling Fan
On Site Laundry
Other spaces
Workspace, Kitchen
Price drop
Renovated Rowhome in the Heart of Downtown Annapolis Historic District!
10
Excellent
·
Annapolis
·
2 br
·
Sleeps 4
·
Oven · Outdoor Space · Fireplace ·
From
$375/nightProperty
House · 2 Beds · 2 baths
Amenities
Oven
Fireplace
Central Heat
Furnished
In Unit Laundry
Dishwasher
Assigned Parking
Air Conditioning
Other spaces
Kitchen, Workspace
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.
Ideal Eastport/ Annapolis Location
10
Excellent
·
Annapolis
·
1 br
·
Sleeps 2
·
Outdoor Space · Oven · Wifi ·
From
$183/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Oven
Wifi
Furnished
Air Conditioning
Onsite Management
Dishwasher
On Site Laundry
Other spaces
Kitchen
Price drop
Gracie's Garden in Annapolis
No rating
·
Annapolis
·
1 br
·
Sleeps 4
·
Furnished · On Site Laundry · Outdoor Space ·
From
$307/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Furnished
On Site Laundry
Wifi
Residents Lounge
Air Conditioning
Business Center
Oven
Assigned Parking
Other spaces
Kitchen, Workspace
Historic Home with Parking Steps From Capital & USNA
No rating
·
Annapolis
·
1 br
·
Sleeps 4
·
Wifi · Furnished · Air Conditioning ·
From
$225/nightProperty
House · 1 Bed · 2 baths
Amenities
Wifi
Furnished
Air Conditioning
Oven
Dishwasher
Hot Tub
On Site Laundry
Other spaces
Kitchen
Expand your search criteria to see more vacation rentals near Annapolis.
Updated: September 23, 2023
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