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.

Annapolis Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
119 rentals in Annapolis.
Sort by:
Tripadvisor Sort
Stunning Home in the Heart of Downtown Annapolis
3 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2. Private 20 acre waterfront estate - studio apt
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful Murray Hill Home (Annapolis)
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
6 other travellers have booked this property
Charming and Spacious Annapolis Victorian
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
31 other travellers have booked this property
Charming Townhouse - Steps to City Dock and USNA
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 other travellers have booked this property
Walk to Shops/Eateries Charming Cottage. Dogs Wel.
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 other travellers have booked this property
*BOOK NOW* Beautiful Cottage in historic Annapolis
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 other travellers have booked this property
Charming Artists Home in Eastport/Annapolis
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Excellent Location in Downtown Annapolis- walk to everything !
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
4 other travellers have booked this property
Location,location,location,walk to city dock,free
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Charming Eastport Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Annapolis Area Waterfront Home
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Perfect Annapolis with Lots of Parking & Hot Tub
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Heart of the Historic District!
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Charming historic home just steps from Main Street!
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Historic Downtown Charmer, Water Views and Parking!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Gorgeous Luxury Home steps to USNA/State House/City Dock
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Beautiful Waterfront Townhome In Historic Annapolis
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Steps Away from Historic Downtown / Close to USNA
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Annapolis Condominium in the Heart of Historic Downtown
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Heart of Downtown, superior location!
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Historic District - 1 Block to Naval Academy & State House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
LUXURY DOWNTOWN HOME - WALK TO EVERYTHING ANNAPOLIS HAS TO OFFER!
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Extended Stays Available Please contact for Availability and Pricing.
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Large Luxury Apartment In Downtown Annapolis
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Historic Annapolis Home And Garden
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Sleeps 10! Great Reviews.
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Less Than A Block From Main Street - Heart Of Historic District!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
OFFICER'S QUARTERS. A 5 BR Luxurious Historic Annapolis Home. Steps to USNA.
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
PERFECT LOCATION in the heart of history
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Two Blocks to Town, Underground Parking Garage
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Charming Annapolis Home w/ Yard - 5 Mins to Dwtn!
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Annapolis House w/ Patio in Bay Ridge Maryland!
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
WALK TO THE STADIUM! Gorgeous, newly built 5 bedroom home.
5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Charming garden row home, easy 4 block walk to the heart of Annapolis.
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Location Location Location!!!50 Steps from Main Street and all of the action
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Private 2 BR Apt -- Less than 1 mi to Downtown & USNA gate
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Jode's Retreat' Your Home Away From Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Historic District, across from Naval Academy, walk to St. John's College.
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Extended Stays Available Please contact for Availability and Pricing.
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
“Athens of America,” Annapolis Apartment One B
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
0025 Bella Chateau. SPECIAL Commissioning Week 2021 Discount! Ask!
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Waterside with it All! Private Pier, Hot Tub and Pool.
6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
The Kings Court - Downtown 4 BR Gem, One Block to the Naval Academy Gates!
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Historic Grandeur in the Heart of Downtown
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Homeaway.co.uk logo
Check-in
Check-out
Previous