We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows:
Internet Explorer
,
Mozilla Firefox
,
Google Chrome
. Mac:
Safari
.
Flights
Holiday Rentals
Restaurants
Things to do
Skip to main content
Review
Trips
Alerts
Sign in
Basket
Inbox
See all
Sign in
to get trip updates and message other travellers.
Annapolis
Annapolis Tourism
Annapolis Hotels
Annapolis Bed and Breakfast
Annapolis Holiday Rentals
Annapolis Packages
Flights to Annapolis
Annapolis Restaurants
Annapolis Attractions
Annapolis Travel Forum
Annapolis Pictures
Annapolis Map
Annapolis Guide
Hotels
All Annapolis Hotels
Annapolis Hotel Deals
Last Minute Hotels in Annapolis
By Hotel Type
By Hotel Class
By Hotel Brand
Popular Amenities
Popular Annapolis Categories
Near Airports
Near Colleges
Annapolis Motels
Family Hotels in Annapolis
Romantic Hotels in Annapolis
Annapolis Beach Hotels
Business Hotels Annapolis
Annapolis Green Hotels
Luxury Hotels in Annapolis
5-stars Hotels in Annapolis
4-stars Hotels in Annapolis
3-stars Hotels in Annapolis
Hilton Garden Inns in Annapolis
Extended Stay America Hotels in Annapolis
Choice Hotels in Annapolis
Hilton Hotels in Annapolis
InterContinental (IHG) Hotels in Annapolis
Marriott Hotels in Annapolis
Annapolis Hotels with a Pool
Pet Friendly Hotels in Annapolis
Annapolis Hotels with Free Wifi
Annapolis Hotels With Indoor Pools
Quiet Hotels in Annapolis
Annapolis Pet Friendly Motels
Cool & Unique Hotels Annapolis
Honeymoon Hotels Annapolis
Hotels with Kitchenette in Annapolis
Charming Hotels in Annapolis
Annapolis Hotels with Smoking Rooms
Boutique Hotels Annapolis
Hotels near (DCA) Ronald Reagan National Airport
Hotels near (IAD) Dulles Intl Airport
Hotels near (BWI) Balt.-Wash. Intl Airport
Hotels near United States Naval Academy
Hotels near Anne Arundel Community College
Things to do
Restaurants
Flights
Holiday Rentals
By Holiday Rental Type
Popular Amenities
Places of Interest
House Rentals in Annapolis
Cheap Annapolis Holiday Rentals
Annapolis Luxury Holiday Rentals
Pet Friendly Rentals in Annapolis
Kid Friendly Annapolis Holiday Rentals
Downtown Annapolis Holiday Rentals
Holiday Rentals near Sandy Point State Park
Holiday Rentals near Annapolis Historic District
Holiday Rentals near Severna Park Lanes
Holiday Rentals near Beverly Triton Beach Park
Shopping
Package Holidays
Cruises
Car Hire
Tours
Add a Place
Travel Forum
Airlines
Travellers' Choice
Help Centre
Travel Stories
Annapolis Pet Friendly Holiday Rentals
Holiday Rentals
USA
Maryland (MD)
Annapolis
Pet Friendly Rentals in Annapolis
Search
Pet Friendly Holiday Rentals in Annapolis
List your property
Owner log in
Where to?
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
View Map
Bedrooms
Any
Bathrooms
Any
Amenities
Internet (77)
Air Conditioning (77)
Washer/Dryer (76)
Wi-Fi (74)
Show all
Suitability
Pet friendly (80)
Kid friendly (75)
Elder access (3)
Smoking allowed (1)
Show more
Property type
Holiday Rental House (70)
Condominium/Apartment (10)
Cabin Holiday Rental (0)
Private Room (0)
Show more
Distinctive Features
Waterfront (14)
Boat Available (2)
Water Views (2)
Private Chef (0)
Show all
Distance from
1 km
80 rentals
in Annapolis.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order.
Learn more.
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
113 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Charming historic home just steps from Main Street!
162 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Beautiful Waterfront Townhome In Historic Annapolis
102 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Annapolis Condominium in the heart of the historic center
202 reviews
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Water Views - Close to Downtown Annapolis
31 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Beautiful Historic Home With Great Location!
64 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Renovated Historic Home located downtown with parking - Walk everywhere !
210 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Quiet Relaxing Waterfront Suisse Chalet - Winter Specials, Great Wedding Venue
39 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
72 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Charming Historic Annapolis with Impressive Updates Throughout
24 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Save time - get the best
Annapolis
rentals sent straight to your email!
Get the List
Historic District Renovated Home Available for 2023 Legislative Session
53 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!
77 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Best Location. Best Price. Across from Gate One & Steps from the Waterfront
75 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Upscale home with parking for 4 cars in driveway. Walk to downtown.
74 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis
20 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Historic District"Crab Cakes and Football"
33 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Nautical Feel to This Beautiful Eastport Home
21 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Perfect historic home + Peloton, walk to downtown Annapolis
21 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Great Location! Walk to Downtown Annapolis, w/ full kitchen washer/dryer...
60 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Excellent Location, Super Clean, Super Spacious !!
18 reviews
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Waterfront Chesapeake Cottage in Oyster Bay - Dock
25 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Beautifully furnished home close to Navy Stadium with Parking!
16 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Large Luxury Apartment In Downtown Annapolis
27 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Charming Annapolis WaterVIEW Home
28 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 13
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Warm and welcoming Eastport home. Gracious sophistication in an ideal location.
15 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Beautiful family-friendly 4-Bdr home in Murray Hill
18 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Parking & Pet Friendly USNA-themed Annapolis home
15 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
ACROSS FROM STADIUM - walk to downtown Annapolis.
24 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Little Magothy Riverfront Home With Pool
13 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
All-stop. Rental Midships.
13 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Relaxing Bay Ridge Lagoon
14 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
10 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Parking and Pet Friendly Annapolis-themed home
9 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Less than a block from Main Street - Heart Of Historic District!
12 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Pet Friendly 2nd Floor Lofted apartment in Eastport
7 reviews
Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
The Navy House~ Walk to Downtown! 3 Bed Bungalow across from Navy Stadium
8 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
NEW! Waterfront Annapolis Getaway w / Fishing Pier!
15 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Beach Neighborhood Minutes From Naval Academy
4 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Cool 1870's Historic District Home with modern amenities
6 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Eastport Peninsula Charm
5 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Get Away On The Bay!
5 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Suburban 3 Bedroom Home, Just 2 Miles From Downtown Annapolis
2 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Everything's New - Annapolis Treasure
2 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Annapolis Garden Suite
1 review
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Private Pet-friendly Coastal Suite with water views just minutes to Annapolis
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Payment Protection
Admiral's Retreat - Pet friendly, 1 mile to Navy Stadium with Parking!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Payment Protection
Eastport Gem - Popular house Walk to Downtown & USNA
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Payment Protection
Adorable home steps from Navy Stadium!
1 review
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
The Heart of Historic Cool in Annapolis
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Payment Protection
Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Pet friendly
More info
Check-in
Check-out
Show Prices
Payment Protection
Previous
Next
1
2