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.

Holiday Rentals in Annapolis

List your property
Owner log in
Where to?
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 km
405 rentals in Annapolis.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
Charming historic home  just steps from Main Street!, holiday rental in Annapolis
Charming historic home  just steps from Main Street!, holiday rental in Annapolis
Charming historic home  just steps from Main Street!, holiday rental in Annapolis

Charming historic home just steps from Main Street!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, holiday rental in Annapolis
Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, holiday rental in Annapolis
Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, holiday rental in Annapolis

Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis

Charming Historic Annapolis Home With Two Off-street Parking Places!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis

Stunning Waterfront Cottage with Breathtaking Views!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Annapolis waterfront "tiny house" in garden setting, holiday rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, holiday rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, holiday rental in Annapolis

Annapolis waterfront "tiny house" in garden setting

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

The Yellow Cottage on Harness Creek, holiday rental in Annapolis
The Yellow Cottage on Harness Creek, holiday rental in Annapolis
The Yellow Cottage on Harness Creek, holiday rental in Annapolis

The Yellow Cottage on Harness Creek

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Brand new Renovation in Historic District with 2 parking spots -walk everywhere, holiday rental in Annapolis
Brand new Renovation in Historic District with 2 parking spots -walk everywhere, holiday rental in Annapolis
Brand new Renovation in Historic District with 2 parking spots -walk everywhere, holiday rental in Annapolis

Brand new Renovation in Historic District with 2 parking spots -walk everywhere

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, holiday rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, holiday rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, holiday rental in Annapolis

One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis

Waterfront Oasis in Eastport - Walk to Downtown and USNA

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Save time - get the best Annapolis rentals sent straight to your email!
Stunning Home in Historic District, Steps to USNA & Downtown, holiday rental in Annapolis
Stunning Home in Historic District, Steps to USNA & Downtown, holiday rental in Annapolis
Stunning Home in Historic District, Steps to USNA & Downtown, holiday rental in Annapolis

Stunning Home in Historic District, Steps to USNA & Downtown

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Two Blocks to Town, Underground Parking Garage, holiday rental in Annapolis
Two Blocks to Town, Underground Parking Garage, holiday rental in Annapolis
Two Blocks to Town, Underground Parking Garage, holiday rental in Annapolis

Two Blocks to Town, Underground Parking Garage

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

PERFECT LOCATION in the heart of history, holiday rental in Annapolis
PERFECT LOCATION in the heart of history, holiday rental in Annapolis
PERFECT LOCATION in the heart of history, holiday rental in Annapolis

PERFECT LOCATION in the heart of history

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

La Maison - Stunning waterfront views with pool, holiday rental in Annapolis
La Maison - Stunning waterfront views with pool, holiday rental in Annapolis
La Maison - Stunning waterfront views with pool, holiday rental in Annapolis

La Maison - Stunning waterfront views with pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

The Cottage on Spa Creek, holiday rental in Annapolis
The Cottage on Spa Creek, holiday rental in Annapolis
The Cottage on Spa Creek, holiday rental in Annapolis

The Cottage on Spa Creek

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Beautiful Waterfront Townhome In Historic Annapolis, holiday rental in Annapolis
Beautiful Waterfront Townhome In Historic Annapolis, holiday rental in Annapolis
Beautiful Waterfront Townhome In Historic Annapolis, holiday rental in Annapolis

Beautiful Waterfront Townhome In Historic Annapolis

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis

Historic Downtown Charmer, Water Views and Parking!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Beautiful Historic Home With Great Location!, holiday rental in Annapolis
Beautiful Historic Home With Great Location!, holiday rental in Annapolis
Beautiful Historic Home With Great Location!, holiday rental in Annapolis

Beautiful Historic Home With Great Location!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis

Renovated Historic Home located downtown with parking - Walk everywhere !

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Annapolis Condominium in the heart of the historic center, holiday rental in Annapolis
Annapolis Condominium in the heart of the historic center, holiday rental in Annapolis
Annapolis Condominium in the heart of the historic center, holiday rental in Annapolis

Annapolis Condominium in the heart of the historic center

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, holiday rental in Annapolis
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, holiday rental in Annapolis
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, holiday rental in Annapolis

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, holiday rental in Annapolis
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, holiday rental in Annapolis
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, holiday rental in Annapolis

Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, holiday rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, holiday rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, holiday rental in Annapolis

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, holiday rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, holiday rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, holiday rental in Annapolis

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

Stunning Annapolis Home! Across from the library, walk to Naval Graduation, holiday rental in Annapolis
Stunning Annapolis Home! Across from the library, walk to Naval Graduation, holiday rental in Annapolis
Stunning Annapolis Home! Across from the library, walk to Naval Graduation, holiday rental in Annapolis

Stunning Annapolis Home! Across from the library, walk to Naval Graduation

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Charming Annapolis Victorian, holiday rental in Annapolis
Charming Annapolis Victorian, holiday rental in Annapolis
Charming Annapolis Victorian, holiday rental in Annapolis

Charming Annapolis Victorian

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Tastefully decorated Eastport Annapolis house with water views, holiday rental in Annapolis
Tastefully decorated Eastport Annapolis house with water views, holiday rental in Annapolis
Tastefully decorated Eastport Annapolis house with water views, holiday rental in Annapolis

Tastefully decorated Eastport Annapolis house with water views

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Space & Relaxation you Crave ! With plenty of Parking!, holiday rental in Annapolis
Space & Relaxation you Crave ! With plenty of Parking!, holiday rental in Annapolis
Space & Relaxation you Crave ! With plenty of Parking!, holiday rental in Annapolis

Space & Relaxation you Crave ! With plenty of Parking!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Historic Annapolis Home And Garden, holiday rental in Annapolis
Historic Annapolis Home And Garden, holiday rental in Annapolis
Historic Annapolis Home And Garden, holiday rental in Annapolis

Historic Annapolis Home And Garden

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Annapolis
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Annapolis
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Annapolis

THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Location Location Location!!!50 Steps from Main Street and all of the action

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis
Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis
Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis

Welcome Aboard the Kathleen Marie!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Heart of Historic District!, holiday rental in Annapolis
Heart of Historic District!, holiday rental in Annapolis
Heart of Historic District!, holiday rental in Annapolis

Heart of Historic District!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, holiday rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, holiday rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, holiday rental in Annapolis

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Eastport Cottage .5 mi from Downtown Annapolis, holiday rental in Annapolis
Eastport Cottage .5 mi from Downtown Annapolis, holiday rental in Annapolis
Eastport Cottage .5 mi from Downtown Annapolis, holiday rental in Annapolis

Eastport Cottage .5 mi from Downtown Annapolis

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Charming cottage - easy walk to downtown with parking, holiday rental in Annapolis
Charming cottage - easy walk to downtown with parking, holiday rental in Annapolis
Charming cottage - easy walk to downtown with parking, holiday rental in Annapolis

Charming cottage - easy walk to downtown with parking

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis, holiday rental in Annapolis
Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis, holiday rental in Annapolis
Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis, holiday rental in Annapolis

Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Come enjoy Historic Annapolis!, holiday rental in Annapolis
Come enjoy Historic Annapolis!, holiday rental in Annapolis
Come enjoy Historic Annapolis!, holiday rental in Annapolis

Come enjoy Historic Annapolis!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Historic District Home with Gorgeous Renovation, holiday rental in Annapolis
Historic District Home with Gorgeous Renovation, holiday rental in Annapolis
Historic District Home with Gorgeous Renovation, holiday rental in Annapolis

Historic District Home with Gorgeous Renovation

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Charming Historic Annapolis with Impressive Updates Throughout, holiday rental in Annapolis
Charming Historic Annapolis with Impressive Updates Throughout, holiday rental in Annapolis
Charming Historic Annapolis with Impressive Updates Throughout, holiday rental in Annapolis

Charming Historic Annapolis with Impressive Updates Throughout

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out

Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis

Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out

Walk to Naval Academy + City Dock, holiday rental in Annapolis
Walk to Naval Academy + City Dock, holiday rental in Annapolis
Walk to Naval Academy + City Dock, holiday rental in Annapolis

Walk to Naval Academy + City Dock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

Walk everywhere . . .just minutes to historic Annapolis,  Updated., holiday rental in Annapolis
Walk everywhere . . .just minutes to historic Annapolis,  Updated., holiday rental in Annapolis
Walk everywhere . . .just minutes to historic Annapolis,  Updated., holiday rental in Annapolis

Walk everywhere . . .just minutes to historic Annapolis, Updated.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis, holiday rental in Annapolis
Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis, holiday rental in Annapolis
Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis, holiday rental in Annapolis

Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Beautiful Condo - Water View Near City Dock, holiday rental in Annapolis
Beautiful Condo - Water View Near City Dock, holiday rental in Annapolis
Beautiful Condo - Water View Near City Dock, holiday rental in Annapolis

Beautiful Condo - Water View Near City Dock

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!, holiday rental in Annapolis
0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!, holiday rental in Annapolis
0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!, holiday rental in Annapolis

0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Historic District'Crab Cakes and Football', holiday rental in Annapolis
Historic District'Crab Cakes and Football', holiday rental in Annapolis
Historic District'Crab Cakes and Football', holiday rental in Annapolis

Historic District'Crab Cakes and Football'

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Water Views - Close to Downtown Annapolis, holiday rental in Annapolis
Water Views - Close to Downtown Annapolis, holiday rental in Annapolis
Water Views - Close to Downtown Annapolis, holiday rental in Annapolis

Water Views - Close to Downtown Annapolis

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Waterfront Chesapeake Cottage in Oyster Bay - Dock, holiday rental in Annapolis
Waterfront Chesapeake Cottage in Oyster Bay - Dock, holiday rental in Annapolis
Waterfront Chesapeake Cottage in Oyster Bay - Dock, holiday rental in Annapolis

Waterfront Chesapeake Cottage in Oyster Bay - Dock

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, holiday rental in Annapolis
Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, holiday rental in Annapolis
Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, holiday rental in Annapolis

Best Location. Best Price. Across from Gate One & Steps from the Waterfront

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

PreviousNext
123456
Frequently Asked Questions about Annapolis